Question:

What is the average price for a 10 ml bottle of pharmacuitical grade tesosterone cyponate?

Answer:

Most 10 ml bottles of testosterone cypionate run about $60 - $70 United States.

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A wine bottle is a bottle used for holding wine, generally made of glass. Some wines are fermented in the bottle, others are bottled only after fermentation. Recently, the bottle has become a standard unit of volume to describe sales in the wine industry, measuring 750 ml.][ However, bottles are produced in a variety of volumes and shapes. Wine bottles are traditionally sealed with cork, but screw-top caps are becoming popular, and there are several other methods used to seal a bottle. The chart below expresses the sizes of various wine bottles in multiples relating to a standard bottle of wine, which is 0.75 litres (0.20 U.S. gal; 0.16 imp gal). Many common sizes are named for Biblical kings and historical figures. Most champagne houses are unable to carry out secondary fermentation in bottles larger than a magnum due to the difficulty in riddling large, heavy bottles. After the secondary fermentation completes, the champagne must be transferred from the magnums into larger bottles, which results in a loss of pressure. Some believe this re-bottling exposes the champagne to greater oxidation and therefore results in an inferior product compared to champagne which remains in the bottle in which it was fermented. * For many years, the U.S. standard (non-metric) wine and liquor bottle was the "fifth", meaning one-fifth of a U.S. gallon, or 25.6 U.S. fluid ounces (757 ml; 26.6 imp fl oz). Some beverages also came in tenth-gallon, half-gallon and one-gallon sizes. In 1979, the U.S. adopted the metric system for wine bottles, with the basic bottle becoming 750 ml, as in Europe.][ Wine producers in Portugal, Italy, Spain, France and Germany follow the tradition of their local areas in choosing the shape of bottle most appropriate for their wine. Many North and South American, South African, and Australasian wine producers select the bottle shape with which they wish to associate their wines. For instance, a producer who believes his wine is similar to Burgundy may choose to bottle his wine in Burgundy-style bottles. Other producers (both in and out of Europe) have chosen idiosyncratic bottle styles for marketing purposes. Pere-Anselme markets its Châteauneuf-du-Pape in bottles that appear half-melted. The Moselland company of Germany has a riesling with a bottle in the shape of a house cat. The home wine maker may use any bottle, as the shape of the bottle does not affect the taste of the finished product. The sole exception is in producing sparkling wine, where thicker-walled bottles should be used to handle the excess pressure. Most wine bottles standards have a bore (inner neck) diameter of 18.5 at the mouth of the bottle and increase to 21 mm before expanding into the full bottle. The traditional colours used for wine bottles are: Clear colourless bottles have recently become popular with white wine producers in many countries, including Greece, Canada and New Zealand. Dark-coloured bottles are most commonly used for red wines, but many white wines also still come in dark green bottles. The main reason for using coloured or tinted glass is that natural sunlight can break down desirable antioxidants such as vitamin c and tannins in a wine over time, which affects storability and can cause a wine to prematurely oxidise. Dark glass can prevent oxidation and increase storage life. It is therefore mostly ready-to-drink white wines with a short anticipated storage lifespan which are bottled in clear colourless bottles. Commercial corked wine bottles typically have a protective sleeve called a foil (commonly referred to as a "capsule") covering the top of the bottle. The purpose of which is to protect the cork from being gnawed away by rodents or infested with the cork weevil and to serve as collar to catch small drips when pouring. The foil also serves as a decorative element of the bottle's label. Foils were historically made of lead; However, because of research showing that trace amounts of toxic lead could remain on the lip of the bottle and mix with the poured wine, lead foil bottleneck wrapping were slowly phased out, and by the 1990s, most foils were made of tin, heat-shrink plastic (polyethylene or PVC), or aluminium or polylaminate aluminium. Sealing wax is sometimes used, or the foil can be omitted entirely. In the US, the FDA officially banned lead foils on domestic and imported wine bottles as of 1996. Some bottles of wine have a paper strip beneath the foil, as a seal of authenticity, which must be broken before the bottle can be uncorked. A punt, also known as a kick-up, refers to the dimple at the bottom of a wine bottle. There is no consensus explanation for its purpose. The more commonly cited explanations include: Glass retains its colour on recycling, and the United Kingdom has a large surplus of green glass because it imports a large quantity of wine but produces very little. 1.4 million tonnes are sent to landfill annually. Glass is a relatively heavy packing material and wine bottles use quite thick glass, so the tare weight of a full wine bottle is a relatively high proportion of its gross weight. The average weight of an empty 75 cl wine bottle is 500 g (and can range from 300 to 900 g), which makes the glass 40% of the total weight of the full bottle. This has led to suggestions that wine should be exported in bulk from producer regions and bottled close to the market. This would reduce the cost of transportation and its carbon footprint, and provide a local market for recycled green glass. Less radically, box wine is sold in large-size light cardboard and foil containers, though its use has been restricted to cheaper products in the past and as such retains a stigma. Some wine producers are exploring more alternative packagings such as plastic bottles and tetra packs.][
Bottled water is drinking water (e.g., well water, distilled water, Mineral water, or spring water) packaged in plastic or glass water bottles. Bottled water may be carbonated or not. Sizes range from small single serving bottles to large carboys for water coolers. The global bottled water sales have increased dramatically over the past several decades, reaching a valuation of around $60 billion and a volume of more than 115,000,000 cubic metres (3.01010 US gal) in 2006. U.S. sales reached around 30 billion bottles of water in 2008, a slight drop from 2007 levels The rate of consumption more than quadrupled between 1990 and 2005. Spring water and purified tap water are currently the leading global sellers. By one estimate, approximately 50 billion bottles of water are consumed per annum in the U.S. and around 200 billion bottles globally. Bottled water is often stored as part of an emergency kit in case of natural disaster. Commonly, disaster management experts recommend storing 1-US-gallon (3.8 L) of water per person, per day. This amount is intended to include water for drinking and cooking as well as water for hand washing, washing dishes, and personal hygiene. Factory-containers of water have an indefinite shelf life, as long as they remain unopened and undamaged. The sell-by date is voluntarily and individually set by manufacturers to indicate the length of time that they believe the water will taste and smell fresh, rather than to indicate any issue of contamination or food safety. In the United States, bottled water and tap water are regulated by different federal agencies: the Food and Drug Administration (FDA) regulates bottled water and the Environmental Protection Agency (EPA) regulates the quality of tap water. Under the Safe Drinking Water Act the EPA has set maximum contaminant levels for approximately 90 contaminants that might be found in drinking water and 15 secondary maximum contaminant levels. Often, enforcement and monitoring of water quality is uneven and irregular for both tap water and bottled water. While tap water contamination incidents must be reported promptly to the public, the same is not true for bottled water, and while contamination of bottled water does occur, many instances have never received public notice until recently (see, for example, the list of more than 100 bottled water recalls). Since the 1950s, tap water is often treated with fluoride to prevent tooth decay. Since bottled water processed with distillation or reverse osmosis lacks fluoride ions which are present in some natural ground water, it is possible that the drinking of distilled water may increase the risk of tooth decay due to a lack of this element now added to many water supplies. Social and scientific issues surrounding the fluoridation of water supplies are discussed in more detail in the articles on water fluoridation and the water fluoridation controversy. According to a 1999 NRDC study, in which roughly 22 percent of brands were tested, at least one sample of bottled drinking water contained chemical contaminants at levels above strict state health limits. Some of the contaminants found in the study could pose health risks if consumed over a long period of time. The NRDC report conceded that "most waters contained no detectable bacteria, however, and the level of synthetic organic chemicals and inorganic chemicals of concern for which [they] were tested were either below detection limits or well below all applicable standards." Meanwhile, a report by the Drinking Water Research Foundation found that of all samples tested by NRDC, "federal FDA or EPA limits were allegedly exceeded only four times, twice for total coliforms and twice for fluorides." Another study, conducted by the Goethe University at Frankfurt found that a high percentage of the bottled water contained in plastic containers was polluted with estrogenic chemicals. Although some of the bottled water contained in glass were found polluted with chemicals as well, the researchers believe some of the contamination of water in the plastic containers may have come from the plastic containers. Leaching of chemicals into the water is related to the plastic bottles being exposed to either low or high temperatures. Bottled noncarbonated drinking water competes in the marketplace with carbonated beverages (including carbonated water) sold in individual plastic bottles. Consumption of water often is considered a healthier substitute for sodas. According to the Container Recycling Institute, sales of flavored, noncarbonated drinks are expected to surpass soda sales by 2010. In response, Coca-Cola and Pepsi-Cola have introduced new carbonated drinks that are fortified with vitamins and minerals, Diet Coke Plus and Tava, marketed as "sparkling beverages." In the United States, bottled water often costs up to $3 per bottle, while a similar volume of tap water costs less than one cent. In 1999, according to a NRDC study, U.S. consumers paid between 240 and 10,000 times more per unit volume for bottled water than for tap water. Typically 90 percent or more of the cost paid for bottled water is for things such as bottling, packaging, shipping, marketing, retailing, and profit, but not for the water itself. In some areas, tap water may contain added fluoride, which helps prevent tooth decay and cavities. Most bottled water manufacturers in the United States either add fluoride to their product or provide a fluoridated bottled water product. The Food and Drug Administration of the United States does not require bottled water manufacturers to list the fluoride content on the label. Water fluoridation remains controversial in countries where forced fluoridation is practiced (the United States, United Kingdom, Ireland, Canada, Australia, and a handful of other countries). Bottled water may have reduced amounts of copper, lead, and other metal contaminants since it does not run through the plumbing pipes where tap water is exposed to metal corrosion, however, this varies by the household and plumbing system. In a study comparing 57 bottled water samples and tap water samples, all of the tap water samples had a bacterial content under 3 CFUs/mL(colony-forming unit) and the bottled water samples' bacterial content ranged from 0.01-4900 CFUs/mL. Most of the water bottle samples were under 1 CFU/mL, although there were 15 water bottle samples containing 6-4900 CFUs/mL. In another study comparing 25 different bottled waters, most of the samples exceeded the contaminant level set by the U.S. Environmental Protection Agency (EPA) for mercury, thallium, and thorium. In much of the developed world chlorine often is added as a disinfectant to water. If the water contains organic matter, this may produce other byproducts in the water such as trihalomethanes and haloacetic acids, resulting in off-smell or taste. The level of residual chlorine found at around 0.0002 g per litre, which is too small to cause any health problems directly. The chlorine concentration recommended by World Health Organization is between 0.0005 and 0.0002 g/L. The Natural Resources Defense Council, Sierra Club, and World Wildlife Fund have urged their supporters to consume less bottled water. Anti-bottled-water-campaigns and organizations, such as Corporate Accountability International, typically argue that bottled water is no better than tap water, and emphasize the detrimental environmental side-effects of disposable plastic bottles. The Showtime series Penn & Teller: Bullshit! demonstrated, in a 2003 episode, that in a controlled setting, restaurant diners could not discern between bottled water and water from a garden hose behind the restaurant. The United Church of Christ, United Church of Canada, National Council of Churches, National Coalition of American Nuns, and Presbyterians for Restoring Creation are among some of the religious organizations that have raised questions about whether or not the "privatization" of water is ethical. They regard the industrial purchase and repackaging at a much higher resale price of a basic resource as an unethical trend. Another frequent criticism of bottled water is the control of limited water sources by private companies, often with the result of closing access to those resources by local peoples, and the near global monopoly of those resources by a small number of corporations, most particularly Nestlé S.A., the World's largest producer of bottled water. The recent documentary Tapped argues against the bottled water industry, asserting that tap water is healthier, more environmentally sustainable, and more ecologically sound than bottled water. The film focuses on the bottled water industry in the United States. The film has received largely positive reviews, and has spawned college campus groups such as Beyond the Bottle. In February 2012, the Grand Canyon National Park Service has approved a plan that would eliminate the sale of bottled water within 30 days. Visitors can use 10 water stations to refill their own water bottles, which they can tote in from the outside, based on concerns that empty plastic bottles scattered around the park are spoiling views of the natural wonder. Another environmental factor is the amount of energy used to manufacture and ship the bottled water. The companies must pump the water out of a spring or municipal source, filter it, create the bottles, fill the bottles, package the bottles, store and chill them, and then ship them all over the country. The amount of energy used in the process to create PET bottles is 100,000 Megajoules (MJ) per ton of PET. There was 100 billion liters of bottled water sold world wide in 2007 which amounted to 3.8 million tons of PET being produced. That comes to 380 billion MJ used in one year on bottle manufacturing. To put that into perspective, the average household uses about 42,864 MJ a year. The FDA has established "Standards of Identity" for bottled water products sold in the U.S. Some of the more common types of bottled water are listed below: Artesian Water This is water that originates from a confined aquifer that has been tapped and in which the water level stands at some height above the top of the aquifer. Fluoridated This type of water contains fluoride added within the limitations established in the FDA Code of Federal Regulations. This category includes water classified as "For Infants" or "Nursery." Ground Water This type of water is from an underground source that is under a pressure equal to or greater than atmospheric pressure. Mineral water Mineral water contains at least 250 parts per million total dissolved solids (TDS). It comes from a source tapped at one or more bore holes or spring, and originates from a geologically and physically protected underground water source. No minerals may be added to this water. Purified Water This type of water has been produced by distillation, deionization, reverse osmosis, or other suitable processes. Purified water may also be referred to as "demineralized water." It meets the definition of "purified water" in the United States Pharmacopoeia. Sparkling Water Sparkling water contains the same amount of carbon dioxide that it had at emergence from the source. The carbon dioxide may be removed and replenished after treatment. Spring Water This type of water comes from an underground formation from which water flows naturally to the Earth's surface. Sterile Water This type of water meets the requirements under "sterility tests" in the United States Pharmacopoeia. Well Water Well water is taken from a hole tapping, etc. This hole may be bored, drilled, or otherwise constructed in the ground. The Beverage Marketing Corporation defines the bottled water market segment as "retail PET, retail bulk, home and office delivery, vending, domestic sparkling and imports", but excluding "flavored and enhanced water." The Plastics Symbol no. 7 is a recent concern worldwide on discovery that large numbers of no.7 plastics are made with Polycarbonate plastic which, experimentally were found to leach bisphenol A. This chemical is a known hormonal disruptor causing miscarriages and birth defects, according to a study conducted by Case Western Reserve scientists. “Synthetic xenoestrogens,” one of which is Bisphenol A or BPA “are linked to breast cancer and uterine cancer in women, decreased testosterone levels in men, and are particularly devastating to babies and young children. BPA has even been linked to insulin resistance and Type 2 Diabetes.” Responsible baby bottle industries are producing BPA-free bottles that are clearly marked. A number of cities and companies worldwide have vending machines that dispense purified water into customer's own containers. All dispensers filter the location's tap water. In North America, these machines are typically located outside of supermarkets. Of all the water vending companies, Glacier Water is by far the largest. Since its inception in 1983, Glacier Water has experienced significant growth in machine placements and has created an extensive network of approximately 17,000 water vending machines (year 2010) located throughout the United States and Canada. Many plumbers install final purification devices into the homes and businesses of customers. Several methods of treatment are offered, ranging from carbon filtration to reverse osmosis and the degree of filtration ranges from making the tap water more palatable to removal of specific minerals and contaminants. Counter-top filtration systems also are sold in grocery and department stores that make tap water more palatable. Similar in principle to traditional canteens that have been used for generations, stainless steel containers for carrying one's personal water supply (drawn from the home or public supply) now are being marketed, however, they are built to resemble contemporary water bottles. Whether that is intended symbolically or as an attempt to fit so many products designed for soda cans or plastic bottles, is uncertain. Similar to glass, stainless steel has been proven as a safe container for water or food for generations because they do not leach any contaminants into its contents. Reverse osmosis water purification systems can remove up to 90% or more of certain inorganic chemicals. These inorganic chemicals include: fluoride, sulfate, nitrate, iron, copper, lead, mercury, arsenic, cadmium, silver and zinc. Reverse osmosis can even remove some microbiological contaminants, including Giardia cysts. However unless equipped with an activated charcoal post-filter, reverse osmosis by itself does not remove dissolved gases and organic chemicals such as radon and trihalomethanes,<http://ag.arizona.edu/pubs/water/az9419.pdf>. It is not uncommon for business or individuals to subscribe to a bottled water service. These services deliver water either monthly or weekly, sometimes even daily. Traditionally, water in glass bottles (jugs) was provided to electric coolers in areas of businesses without plumbing. Plastic containers have replaced those glass jugs, however, dispensers at businesses now may stand alongside of existing water taps or fountains. The Australasian Bottled Water Institute is a regional member of the International Council of Bottled Water Associations. The bottled water industry in Australia is worth approximately $400 million per year, An upmarket restaurant in Sydney has stopped selling bottled water and started using a machine costing A$5000 to filter, chill and carbonate tap water to get the same quality water. In 2009, the New South Wales town of Bundanoon voted to become the first town in the world to outlaw bottled water. Its citizens voluntarily chose to ban bottled water in response to a bottling company's desire to sell water from the town's local aquifer. The initiative was proposed by local businessman Huw Kingston and carried out by the grassroots organization name Bundy On Tap (the name is a pun which refers to Bundaberg, an Australian brand of rum which is sometimes served as a pre-mixed draught). In a community meeting of 356 of the town's 2,500 residents, all but one voted in favor of the ban, prohibiting the selling or dispensing of bottled water within the town precinct. Bundanoon's six stores have removed bottled water from their stock. The town now offers public drinking fountains and filtered water dispensers where people can fill up reusable water bottles and canteens. The reusable empty bottles are sold in place of full bottles in the local stores. Bundanoon's bold stand against bottled water's damaging effects on the environment and on communities has thrust it into a global spotlight. Bundanoon has caught the attention of many other cities around the world who soon could have similar policies. The decision to ban bottled water came partly from opposition to the proposed bottling plant, and partly from opposition to the environmental and health impacts. There is skepticism that singling out bottled water is necessarily the best option, as there is a worry that soft drinks will be purchased more frequently in place of bottled water because of the convenience the disposable bottle offers. Directive 2009/54/EC deals with the marketing and exploitation of natural mineral waters in the European Union. The two main types of bottled water recognized are mineral water and spring water. Broadly speaking, "mineral water" is groundwater that has emerged from the ground and flowed over rock. Treatment of mineral water is restricted to removal of unstable elements such as iron and sulfur compounds. Treatment for such minerals may extend only to filtration or decanting with oxygenation. Free carbon dioxide may be removed only by physical methods, and the regulations for introduction (or reintroduction) of CO2 are strictly defined. Disinfection of natural mineral water is completely prohibited, including the addition of any element that is likely to change bacterial colony counts. If natural mineral water is effervescent, it must be labelled accordingly, depending on the origin of the carbon dioxide: naturally carbonated natural mineral water (no introduction of CO2); natural mineral water fortified with gas from the spring (reintroduction of CO2); carbonated natural mineral water (CO2 added following strict guidelines). Directive 2001/83/EC deals with bottled water that is considered a "medicinal product" and is thus excluded from the scope of the other regulation. Water is the chief natural resource of Lebanon where the porous fractured limestone of the mountains, both the Mount Lebanon and the Anti-Lebanon ranges, create an excellent aquifer that are replenished over spring and early summer by the melting snow. Lebanon has an advantageous position in the region as far as the amount of rainfall the country receives and water resources available where springs are abundant, due to the exceedingly “fractured geologic rocks,” and where streams amount to a length of 730 km. Lebanon has one of the fastest growth rate of per capita consumption of bottled water. Lebanon has seven major brands of bottled mineral water for local consumption and for exportation to the water-starved countries on the Arabian Peninsula and in the Persian Gulf: Almaha, Arz Water, Rim Natural Mineral Water, Sabil, Sannine, Sohat and Tannourine. Bottled water in New Zealand is regulated by Food Standards Australia New Zealand and must comply with the Food Act 1981. From July 2009 fluoride was allowed to be present in bottled water as an additive or as a natural occurring mineral. Due to contaminated water being widespread, in the mid-1980s urban families started installing filtration units at home. This later developed into companies providing mineral water delivery services at home. Use of these 1-US-gallon (3.8 L) bottles that could be attached to a dispenser is still widespread. Bottled water was made famous by one of the largest marketing campaigns in Pakistan history undertaken by Nestle. Eventually, other bottlers including dozens of local ones, Coca Cola, Pepsi, Nature, Vey, Great Water Islamabad, Dew Drop, and other imported brands such as Evian began marketing in the country. The U.S. is the largest consumer market for bottled water in the world, followed by Mexico, China, and Brazil. In 2008, U.S. bottled water sales topped 8.6 billion US gallons (33,000,000 m3) for 28.9% of the U.S. liquid beverage market, exceeding sales of all other beverages except carbonated soft drinks, they are followed by fruit juices, and sports drinks. Americans drink 21 US gallons (79 L) of bottled water per capita per year.
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1Yes 
Key:MUMGGOZAMZWBJJ-DYKIIFRCSA-NYes  Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. In mammals, testosterone is primarily secreted in the testicles of males and the ovaries of females, although small amounts are also secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid. In men, testosterone plays a key role in the development of male reproductive tissues such as the testis and prostate as well as promoting secondary sexual characteristics such as increased muscle, bone mass, and the growth of body hair. In addition, testosterone is essential for health and well-being as well as the prevention of osteoporosis. On average, in adult human males, the plasma concentration of testosterone is about 7–8 times as great as the concentration in adult human females' plasma, but as the metabolic consumption of testosterone in males is greater, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. Testosterone is observed in most vertebrates. Fish make a slightly different form called 11-ketotestosterone. Its counterpart in insects is ecdysone. These ubiquitous steroids suggest that sex hormones have an ancient evolutionary history. In general, androgens promote protein synthesis and growth of those tissues with androgen receptors. Testosterone effects can be classified as virilizing and anabolic, though the distinction is somewhat artificial, as many of the effects can be considered both. Testosterone effects can also be classified by the age of usual occurrence. For postnatal effects in both males and females, these are mostly dependent on the levels and duration of circulating free testosterone. The prenatal androgen effects occur during two different stages. Between 4 and 6 weeks of the gestation. During the second trimester, androgen level is associated with gender formation. This period affects the femininization or masculinization of the fetus and can be a better predictor of feminine or mascular behaviours such as sex typed behaviour than an adult's own levels. A mother's testosterone level during pregnancy is correlated with her daughter's sex-typical behavior as an adult, and the correlation is even stronger than with the daughter's own adult testosterone level. Early infancy androgen effects are the least understood. In the first weeks of life for male infants, testosterone levels rise. The levels remain in a pubertal range for a few months, but usually reach the barely detectable levels of childhood by 4–6 months of age. The function of this rise in humans is unknown. It has been speculated that "brain masculinization" is occurring since no significant changes have been identified in other parts of the body. Surprisingly, the male brain is masculinized by testosterone being aromatized into estrogen, which crosses the blood–brain barrier and enters the male brain, whereas female fetuses have alpha-fetoprotein which binds up the estrogen so that female brains are not affected. Pre- Peripubertal effects are the first observable effects of rising androgen levels at the end of childhood, occurring in both boys and girls. Pubertal effects begin to occur when androgen has been higher than normal adult female levels for months or years. In males, these are usual late pubertal effects, and occur in women after prolonged periods of heightened levels of free testosterone in the blood. Adult testosterone effects are more clearly demonstrable in males than in females, but are likely important to both sexes. Some of these effects may decline as testosterone levels decrease in the later decades of adult life. Falling in love decreases men's testosterone levels while increasing women's testosterone levels. There has been speculation that these changes in testosterone result in the temporary reduction of differences in behavior between the sexes. However, it is suggested that after the "honeymoon phase" ends—some one to three years into a relationship—this change in testosterone levels is no longer apparent. Fatherhood also decreases testosterone levels in men, suggesting that the resulting emotional and behavioral changes promote paternal care. Men who produce less testosterone are more likely to be in a relationship and/or married, and men who produce more testosterone are more likely to divorce; however, causality cannot be determined in this relationship. Marriage or commitment could cause a decrease in T levels. Single men who have not had relationship experience have lower testosterone levels than single men with experience. It is suggested that these single men with prior experience are in a more competitive state than their non-experienced counterparts. Married men who engage in bond-maintenance activities such as spending the day with their spouse/and or child have no different testosterone levels compared to times when they do not engage in such activities. Collectively, these results suggest that the presence of competitive activities rather than bond-maintenance activities are more relevant to changes in T levels. Men who produce more testosterone are more likely to engage in extramarital sex. Testosterone levels do not rely on physical presence of a partner for men engaging in relationships (same-city vs. long-distance), men have similar testosterone levels across the board. Physical presence may be required for women who are in relationships for the testosterone–partner interaction, where same-city partnered women have lower testosterone levels than long-distance partnered women. It has been found that when testosterone and endorphins in ejaculated semen meet the cervical wall after sexual intercourse, females receive a spike in testosterone, endorphin, and oxytocin levels, and males after orgasm during copulation experience an increase in endorphins and a marked increase in oxytocin levels. This adds to the hospitable physiological environment in the female internal reproductive tract for conceiving, and later for nurturing the conceptus in the pre-embryonic stages, and stimulates feelings of love, desire, and paternal care in the male (this is the only time male oxytocin levels rival a female's). Testosterone levels follow a nyctohemeral rhythm which peaks early each day, regardless of sexual activity There are positive correlations between positive orgasm experience in women and testosterone levels where relaxation was a key perception of the experience. There is no correlation between testosterone and men's perceptions of their orgasm experience, and also no correlation between higher testosterone levels and greater sexual assertiveness in either sex. An increase in T levels has also been found to occur in both men and women who have masturbation-induced orgasms. Studies conducted on rats have indicated that their degree of sexual arousal is sensitive to reductions in testosterone. When testosterone-deprived rats were given medium levels of testosterone, their sexual behaviors (copulation, partner preference, etc.) resumed, but not when given low amounts of the same hormone. Therefore, these mammals may provide a model for studying clinical populations among humans suffering from sexual arousal deficits such as hypoactive sexual desire disorder. In one study, almost every mammalian species examined demonstrated a marked increase in a male's testosterone level upon encountering a novel female. P.J. James et al. investigated the role of genotype on such so-called reflexive testosterone increases in male mice. They also concluded that this response is related to the male's initial level of sexual arousal. In non-human primates it has been suggested that testosterone in puberty stimulates sexual motivation, which allows the primate to increasingly seek out sexual experiences with females and thus creates a sexual preference for females. Some research has also indicated that if testosterone is eliminated in an adult male human or other adult male primate's system, its sexual motivation decreases, but there is no corresponding decrease in ability to engage in sexual activity (mounting, ejaculating, etc.). Higher levels of testosterone were associated with periods of sexual activity within subjects, but between subjects testosterone levels were higher for less sexually active individuals. Men who have sexual encounters with unfamiliar or multiple partners experience large increases of testosterone the morning after. Men who watch a sexually explicit movie have an average increase of 35% in testosterone, peaking at 60–90 minutes after the end of the film, but no increase is seen in men who watch sexually neutral films. Men who watch sexually explicit films also report increased optimism and decreased exhaustion. Previous research has found a link between relaxation following sexual arousal and testosterone levels. A 2002 study found that testosterone increased in heterosexual men who had engaged in sexual activity in the past six months after brief conversations with women. The increase in T levels was associated with the intensity of "courtship" behaviours that the men exhibited. Men's levels of testosterone, a hormone known to affect men's mating behaviour, changes depending on whether they are exposed to an ovulating or nonovulating woman's body odour. Men who are exposed to scents of ovulating women maintained a stable testosterone level that was higher than the testosterone level of men exposed to nonovulation cues. Testosterone levels and sexual arousal in men are heavily aware of hormone cycles in females. This may be linked to the ovulatory shift hypothesis, where males are adapted to respond to the ovulation cycles of females by sensing when they are most fertile and whereby females look for preferred male mates when they are the most fertile; both actions may be driven by hormones. In a 1991 study, males were exposed to either visual or auditory erotic stimuli and asked to complete a cognitive task, where the number of errors on the task indicated how distracted the participant was by the stimuli. It concluded that men with lower thresholds for sexual arousal have a greater likelihood to attend to sexual information and that testosterone may have an impact by enhancing their attention to the relevant stimuli. Sperm competition theory: Testosterone levels are shown to increase as a response to previously neutral stimuli when conditioned to become sexual in male rats. This reaction engages penile reflexes (such as erection and ejaculation) that aid in sperm competition when more than one male is present in mating encounters, allowing for more production of successful sperm and a higher chance of reproduction. Androgens may modulate the physiology of vaginal tissue and contribute to female genital sexual arousal. Women's level of testosterone is higher when measured pre-intercourse vs pre-cuddling, as well as post-intercourse vs post-cuddling. There is a time lag effect when testosterone is administered, on genital arousal in women. In addition, a continuous increase in vaginal sexual arousal may result in higher genital sensations and sexual appetitive behaviors. When females have a higher baseline level of testosterone, they have higher increases in sexual arousal levels but smaller increases in testosterone, indicating a ceiling effect on testosterone levels in females. Sexual thoughts also change the level of testosterone but not level of cortisol in the female body, and hormonal contraceptives may have an impact on the variation in testosterone response to sexual thoughts. Testosterone may prove to be an effective treatment in female sexual arousal disorders. Currently there is no FDA approved androgen preparation for the treatment of androgen insufficiency, however it has been used off-label to treat low libido and sexual dysfunction in older women. Testosterone may be a treatment for postmenopausal women as long as they are effectively estrogenized. Testosterone levels play a major role in risk-taking during financial decisions. A 2009 study of 25 male subjects found that men with artificially raised testosterone were 27% less generous while playing a test game than they were at their normal testosterone level. The authors concluded that "What we have found is that T[estosterone] appears to play a role inducing men to change from being selfless to being selfish." As testosterone affects the entire body (often by enlarging; males have bigger hearts, lungs, liver, etc.), the brain is also affected by this "sexual" differentiation; the enzyme aromatase converts testosterone into estradiol that is responsible for masculinization of the brain in male mice. In humans, masculinization of the fetal brain appears, by observation of gender preference in patients with congenital diseases of androgen formation or androgen receptor function, to be associated with functional androgen receptors. There are some differences between a male and female brain (possibly the result of different testosterone levels), one of them being size: the male human brain is, on average, larger. In a Danish study from 2003, men were found to have a total myelinated fiber length of 176,000 km at the age of 20, whereas in women the total length was 149,000 km (approx. 15% less). A study conducted in 1996 found no immediate short term effects on mood or behavior from the administration of supraphysiologic doses of testosterone for 10 weeks on 43 healthy men. Another study found a correlation between testosterone and risk tolerance in career choice among women. The literature suggests that attention, memory, and spatial ability are key cognitive functions affected by testosterone in humans. Preliminary evidence suggests that low testosterone levels may be a risk factor for cognitive decline and possibly for dementia of the Alzheimer's type, a key argument in life extension medicine for the use of testosterone in anti-aging therapies. Much of the literature, however, suggests a curvilinear or even quadratic relationship between spatial performance and circulating testosterone, where both hypo- and hypersecretion (deficient- and excessive-secretion) of circulating androgens have negative effects on cognition. The "evolutionary neuroandrogenic theory" focuses on the hormone testosterone as a factor influencing aggression and criminality and being evolutionarily beneficial during certain forms of competition. In most species, males are more aggressive than females. Castration of males usually has a pacifying effect on their aggressive behavior. In humans, males engage in crime and especially violent crime more than females. Their involvement in crime usually rises in the early teens to mid teens, at the same time as testosterone levels rise. Research on the relationship between testosterone and aggression is difficult since the only reliable measurement of brain testosterone is by a lumbar puncture which is not done for research purposes. Studies therefore have often instead used more unreliable measurements from blood or saliva. Most studies support a link between adult criminality and testosterone although the relationship is modest if examined separately for each sex. Nearly all studies of juvenile delinquency and testosterone are not significant. Most studies have also found testosterone to be associated with behaviors or personality traits linked with criminality such as antisocial behavior and alcoholism. Many studies have also been done on the relationship between more general aggressive behavior/feelings and testosterone. About half the studies have found a relationship and about half no relationship. The testosterone derivative estradiol (an estrogen) is known to correlate with aggression in male mice. Moreover, the conversion of testosterone to estradiol regulates male aggression in sparrows during breeding season. The original and primary use of testosterone is for the treatment of males who have too little or no natural endogenous testosterone production—males with hypogonadism. Appropriate use for this purpose is legitimate hormone replacement therapy (testosterone replacement therapy [TRT]), which maintains serum testosterone levels in the normal range. Testosterone has also been given for many other conditions and purposes besides replacement. Examples include reducing infertility, correcting lack of libido or erectile dysfunction, correcting osteoporosis, encouraging penile enlargement, encouraging height growth, encouraging bone marrow stimulation and reversing the effects of anemia, and even appetite stimulation. By the late 1940s testosterone was being touted as an anti-aging wonder drug (e.g., see Paul de Kruif's The Male Hormone). Decline of testosterone production with age has led to interest in androgen replacement therapy. To take advantage of its virilizing effects, testosterone is often administered to transsexual men as part of the hormone replacement therapy, with a "target level" of the normal male testosterone level. Like-wise, transsexual women are sometimes prescribed anti-androgens to decrease the level of testosterone in the body and allow for the effects of estrogen to develop. Testosterone patches are effective at treating low libido in post-menopausal women. Low libido may also occur as a symptom or outcome of hormonal contraceptive use. Women may also use testosterone therapies to treat or prevent loss of bone density, muscle mass and to treat certain kinds of depression and low energy state. Women on testosterone therapies may experience an increase in body weight without an increase in body fat due to changes in bone and muscle density. The undesired effects of testosterone therapy in women are typically controlled with symptomatic treatments, such as hair removal and topical acne therapy. There is a theoretical risk that testosterone therapy increases the risk of breast or gynaecological cancers, and further research is needed to define any such risks more clearly. Appropriate testosterone therapy may improve the management of type 2 diabetes. Low testosterone has been associated with the development of Alzheimer's disease. A small trial in 2005 showed mixed results in using testosterone to combat the effects of aging. Large scale trials to assess the efficiency and long-term safety of testosterone are still lacking. Testosterone levels decline gradually with age in human beings. The clinical significance of this decrease is debated (see andropause). There is disagreement about when to treat aging men with testosterone replacement therapy. The American Society of Andrology's position is that "testosterone replacement therapy in aging men is indicated when both clinical symptoms and signs suggestive of androgen deficiency and decreased testosterone levels are present." The American Association of Clinical Endocrinologists says "Hypogonadism is defined as a free testosterone level that is below the lower limit of normal for young adult control subjects. Previously, age-related decreases in free testosterone were once accepted as normal. Currently, they are not considered normal. Patients with borderline testosterone levels warrant a clinical trial of testosterone." There is not total agreement on the threshold of testosterone value below which a man would be considered hypogonadal. (Currently there are no standards as to when to treat women.) Testosterone can be measured as "free" (that is, bioavailable and unbound) or more commonly, "total" (including the percentage which is chemically bound and unavailable). In the United States, male total testosterone levels below 300 ng/dL from a morning serum sample are generally considered low. Identification of inadequate testosterone in an aging male by symptoms alone can be difficult. Adverse effects of testosterone supplementation include minor side effects such as acne and oily skin, and more significant complications such as increased hematocrit which can require venipuncture in order to treat, exacerbation of sleep apnea and acceleration of pre-existing prostate cancer growth in individuals who have undergone androgen deprivation. Another adverse effect may be significant hair loss and/or thinning of the hair. This may be prevented with 5-alpha reductase inhibitors ordinarily used for the treatment of benign prostatic hyperplasia such as finasteride or dutasteride. Exogenous testosterone also causes suppression of spermatogenesis and can lead to infertility. Testosterone insufficiency (also termed hypotestosteronism or hypotestosteronemia) is an abnormally low testosterone production. It may occur because of testicular dysfunction (primary hypogonadism) or hypothalamic-pituitary dysfunction (secondary hypogonadism) and may be congenital or acquired. An acquired form of hypotestosteronism is the decline in testosterone levels that occurs by aging, sometimes called "andropause" in men, as a comparison to the decline in estrogen that comes with menopause in women. In Western countries, average testosterone levels are receding in men of all ages. Several theories, from increases in obesity, to exposure to endocrine disruptors have been proposed as an explanation for this reduction. Testosterone can be used by an athlete in order to improve performance, but it is considered to be a form of doping in most sports. There are several application methods for testosterone, including intramuscular injections, transdermal gels and patches, and implantable pellets. Supplement of the hormone results in lower metabolic production via the Farquharson phenomenon, creating long term dependence for improved performance level.][ Anabolic steroids (including testosterone) have also been taken to enhance muscle development, strength, or endurance. They do so directly by increasing the muscles' protein synthesis. As a result, muscle fibers become larger and repair faster than the average person's. After a series of scandals and publicity in the 1980s (such as Ben Johnson's improved performance at the 1988 Summer Olympics), prohibitions of anabolic steroid use were renewed or strengthened by many sports organizations. Testosterone and other anabolic steroids were designated a "controlled substance" by the United States Congress in 1990, with the Anabolic Steroid Control Act. The use is seen as being a seriously problematic issue in modern sport, particularly given the lengths to which athletes and professional laboratories go to in trying to conceal such abuse from sports regulators. Steroid abuse once again came into the spotlight recently as a result of the Chris Benoit double murder-suicide in 2007, and the media frenzy surrounding it – however, there has been no evidence indicating steroid use as a contributing factor. A number of methods for detecting testosterone use by athletes have been employed, most based on a urine test. These include the testosterone/epitestosterone ratio (normally less than 6), the testosterone/luteinizing hormone ratio and the carbon-13 / carbon-12 ratio (pharmaceutical testosterone contains less carbon-13 than endogenous testosterone). In some testing programs, an individual's own historical results may serve as a reference interval for interpretation of a suspicious finding. Another approach being investigated is the detection of the administered form of testosterone, usually an ester, in hair. Exogenous testosterone supplementation comes with a number of health risks. Fluoxymesterone and methyltestosterone are synthetic derivatives of testosterone. Methyltestosterone and fluoxymesterone are no longer prescribed by physicians given their poor safety record, and testosterone replacement in men does have a very good safety record as evidenced by over sixty years of medical use in hypogonadal men. Testosterone in the presence of a slow-growing cancer is assumed to increase its growth rate. However the association between testosterone supplementation and the development of prostate cancer is unproven. Nevertheless physicians are cautioned about the cancer risk associated with testosterone supplementation: Ethnic groups have different incidences of prostate cancer. Differences in sex hormones including testosterone have been suggested as an explanation for these differences. This apparent paradox can be resolved by noting that prostate cancer is very common. In autopsies, 80% of 80 year old men have prostate cancer. Like other steroid hormones, testosterone is derived from cholesterol (see figure to the left). The first step in the biosynthesis involves the oxidative cleavage of the sidechain of cholesterol by CYP11A, a mitochondrial cytochrome P450 oxidase with the loss of six carbon atoms to give pregnenolone. In the next step, two additional carbon atoms are removed by the CYP17A enzyme in the endoplasmic reticulum to yield a variety of C19 steroids. In addition, the 3-hydroxyl group is oxidized by 3-β-HSD to produce androstenedione. In the final and rate limiting step, the C-17 keto group androstenedione is reduced by 17-β hydroxysteroid dehydrogenase to yield testosterone. The largest amounts of testosterone (>95%) are produced by the testes in men. It is also synthesized in far smaller quantities in women by the thecal cells of the ovaries, by the placenta, as well as by the zona reticularis of the adrenal cortex and even skin in both sexes. In the testes, testosterone is produced by the Leydig cells. The male generative glands also contain Sertoli cells which require testosterone for spermatogenesis. Like most hormones, testosterone is supplied to target tissues in the blood where much of it is transported bound to a specific plasma protein, sex hormone binding globulin (SHBG). In males, testosterone is primarily synthesized in Leydig cells. The number of Leydig cells in turn is regulated by luteinizing hormone (LH) and follicle stimulating hormone (FSH). In addition, the amount of testosterone produced by existing Leydig cells is under the control of LH which regulates the expression of 17-β hydroxysteroid dehydrogenase. The amount of testosterone synthesized is regulated by the hypothalamic–pituitary–testicular axis (see figure to the right). When testosterone levels are low, gonadotropin-releasing hormone (GnRH) is released by the hypothalamus which in turn stimulates the pituitary gland to release FSH and LH. These latter two hormones stimulate the testis to synthesize testosterone. Finally, increasing levels of testosterone through a negative feedback loop act on the hypothalamus and pituitary to inhibit the release of GnRH and FSH/LH, respectively. Environmental factors affecting testosterone levels include: Approximately 7% of testosterone is reduced to 5α-dihydrotestosterone (DHT) by the cytochrome P450 enzyme 5α-reductase, an enzyme highly expressed in male sex organs and hair follicles. Approximately 0.3% of testosterone is converted into estradiol by aromatase (CYP19A1) an enzyme expressed in the brain, liver, and adipose tissues. DHT is a more potent form of testosterone while estradiol has completely different activities (feminization) compared to testosterone (masculinization). Finally, testosterone and DHT may be deactivated or cleared by enzymes that hydroxylate at the 6, 7, 15 or 16 positions. The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than testosterone, so that its androgenic potency is about 5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. Androgen receptors occur in many different vertebrate body system tissues, and both males and females respond similarly to similar levels. Greatly differing amounts of testosterone prenatally, at puberty, and throughout life account for a share of biological differences between males and females. The bones and the brain are two important tissues in humans where the primary effect of testosterone is by way of aromatization to estradiol. In the bones, estradiol accelerates ossification of cartilage into bone, leading to closure of the epiphyses and conclusion of growth. In the central nervous system, testosterone is aromatized to estradiol. Estradiol rather than testosterone serves as the most important feedback signal to the hypothalamus (especially affecting LH secretion).][ In many mammals, prenatal or perinatal "masculinization" of the sexually dimorphic areas of the brain by estradiol derived from testosterone programs later male sexual behavior.][ A number of synthetic analogs of testosterone have been developed with improved bioavailability and metabolic half life relative to testosterone. Many of these analogs have an alkyl group introduced at the C-17 position in order to prevent conjugation and hence improve oral bioavailability. These are the so-called "17-aa" (17-alkyl androgen) family of androgens such as fluoxymesterone and methyltestosterone. Some drugs indirectly target testosterone as a way of treating certain conditions. For example, 5-alpha-reductase inhibitors such as finasteride inhibit the conversion of testosterone into dihydrotestosterone (DHT), a metabolite which is more potent than testosterone. These 5-alpha-reductase inhibitors have been used to treat various conditions associated with androgens, such as androgenetic alopecia (male-pattern baldness), hirsutism, benign prostatic hyperplasia (BPH), and prostate cancer. Alternatively GnRH antagonists bind to GnRH receptors in the pituitary gland, blocking the release of luteinising hormone (LH) and follicle-stimulating hormone (FSH) from the pituitary. In men, the reduction in LH subsequently leads to rapid suppression of testosterone release from the testes. GnRH antagonists have been used for the treatment of prostate cancer. There are many routes of administration for testosterone. Forms of testosterone for human administration currently available include injectable (such as testosterone cypionate or testosterone enanthate in oil), oral, buccal, transdermal skin patches, transdermal creams, gels, and implantable pellets. Roll-on methods and nasal sprays are currently under development. A testicular action was linked to circulating blood fractions – now understood to be a family of androgenic hormones – in the early work on castration and testicular transplantation in fowl by Arnold Adolph Berthold (1803–1861). Research on the action of testosterone received a brief boost in 1889, when the Harvard professor Charles-Édouard Brown-Séquard (1817–1894), then in Paris, self-injected subcutaneously a "rejuvenating elixir" consisting of an extract of dog and guinea pig testicle. He reported in The Lancet that his vigor and feeling of well-being were markedly restored but the effects were transient, and Brown-Séquard's hopes for the compound were dashed. Suffering the ridicule of his colleagues, he abandoned his work on the mechanisms and effects of androgens in human beings. In 1927, the University of Chicago's Professor of Physiologic Chemistry, Fred C. Koch, established easy access to a large source of bovine testicles — the Chicago stockyards — and recruited students willing to endure the tedious work of extracting their isolates. In that year, Koch and his student, Lemuel McGee, derived 20 mg of a substance from a supply of 40 pounds of bovine testicles that, when administered to castrated roosters, pigs and rats, remasculinized them. The group of Ernst Laqueur at the University of Amsterdam purified testosterone from bovine testicles in a similar manner in 1934, but isolation of the hormone from animal tissues in amounts permitting serious study in humans was not feasible until three European pharmaceutical giants—Schering (Berlin, Germany), Organon (Oss, Netherlands) and Ciba (Basel, Switzerland)—began full-scale steroid research and development programs in the 1930s. The Organon group in the Netherlands were the first to isolate the hormone, identified in a May 1935 paper "On Crystalline Male Hormone from Testicles (Testosterone)". They named the hormone testosterone, from the stems of testicle and sterol, and the suffix of ketone. The structure was worked out by Schering's Adolf Butenandt. The chemical synthesis of testosterone from cholesterol was achieved in August that year by Butenandt and Hanisch. Only a week later, the Ciba group in Zurich, Leopold Ruzicka (1887–1976) and A. Wettstein, published their synthesis of testosterone. These independent partial syntheses of testosterone from a cholesterol base earned both Butenandt and Ruzicka the joint 1939 Nobel Prize in Chemistry. Testosterone was identified as 17β-hydroxyandrost-4-en-3-one (C19H28O2), a solid polycyclic alcohol with a hydroxyl group at the 17th carbon atom. This also made it obvious that additional modifications on the synthesized testosterone could be made, i.e., esterification and alkylation. The partial synthesis in the 1930s of abundant, potent testosterone esters permitted the characterization of the hormone's effects, so that Kochakian and Murlin (1936) were able to show that testosterone raised nitrogen retention (a mechanism central to anabolism) in the dog, after which Allan Kenyon's group was able to demonstrate both anabolic and androgenic effects of testosterone propionate in eunuchoidal men, boys, and women. The period of the early 1930s to the 1950s has been called "The Golden Age of Steroid Chemistry", and work during this period progressed quickly. Research in this golden age proved that this newly synthesized compound—testosterone—or rather family of compounds (for many derivatives were developed from 1940 to 1960), was a potent multiplier of muscle, strength, and well-being. Testis: testosterone  AMH  inhibin Ovary: estradiol  progesterone  activin and inhibin  relaxin (pregnancy) Thymus: Thymosin (Thymosin α1, Thymosin beta)  Thymopoietin  Thymulin Digestive system: Stomach: gastrin  ghrelin  Duodenum: CCK  Incretins (GIP, GLP-1)   secretin  motilin  VIP  Ileum: enteroglucagon  peptide YY  Liver/other: Insulin-like growth factor (IGF-1, IGF-2) Adipose tissue: leptin  adiponectin  resistin Skeleton: Osteocalcin Kidney: JGA (renin)  peritubular cells (EPO)  calcitriol  prostaglandin M: END anat/phys/devp/horm noco (d)/cong/tumr, sysi/epon proc, drug (A10/H1/H2/H3/H5) M: ♂ MRS anat/phys/devp noco/cong/tumr, sysi/epon proc, drug (G3B/4BE/4C) M: DIG anat (t, g, p)/phys/devp/enzy noco/cong/tumr, sysi/epon proc, drug (A2A/2B/3/4/5/6/7/14/16), blte Note: Anabolic steroids, including those that are only weakly virilizing (or even anti-virilizing (e.g., oxandrolone)), are included here (since their anabolic effects are nonetheless mediated via activation of the androgen receptor). Note: Though not listed here, many anabolic steroids can also be estrogenic as they can be aromatized into estrogen-like metabolites that possess estrogenic activity.
3-Cyclopentylpropanoic acid 3-Cyclopentylpropionic acid; Cypionate; Cipionate O=C(O)CCC1CCCC1 InChI=1S/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10)
Key: ZRPLANDPDWYOMZ-UHFFFAOYSA-N InChI=1/C8H14O2/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2,(H,9,10)
Key: ZRPLANDPDWYOMZ-UHFFFAOYAK 130-132 °C (12 mmHg) Cypionic acid is a carboxylic acid with the molecular formula C8H14O2. Its salts and esters are known as cypionates or cipionates. The primary use of cypionic acid is in pharmaceutical formulations. Cypionic acid is used to prepare ester prodrugs which have increased half-lives relative to the parent compound. The lipophilicity of the cypionate group allows the prodrug to be sequestered in fat depots after intramuscular injection. The ester group is slowly hydrolyzed by metabolic enzymes, releasing steady doses of the active ingredient. Examples include testosterone cypionate, hydrocortisone cypionate, and oxabolone cypionate.
pentanoate d'estra-1,3,5(10)-triène-3-ol-17β-yle InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
Key:RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate (INN, USAN; brand names Altadiol, Deladiol, Delestrogen, Estraval, Progynova, Valergen, many others), or oestradiol valerate (BAN), is a synthetic ester, specifically the 17-pentanoyl ester, of the natural estrogen, 17β-estradiol. It was introduced in the 1950s, and along with estradiol benzoate and estradiol cypionate, has since become one of the most widely used esters of estradiol. Upon ingestion, regardless of the route of administration, estradiol valerate behaves as a prodrug, being cleaved by esterases in blood plasma and the liver into 17β-estradiol and valeric acid. However, compared to estradiol itself, estradiol valerate is absorbed more slowly and possesses a longer duration, especially when given in an oil solution via intramuscular injection (in which it acts as a depot), and as a result, can be administered less frequently.
M: ♀ FRS anat/phys/devp noco/cong/npls, sysi/epon proc/asst, drug (G1/G2B/G3CD) Note: Though not listed here, many anabolic steroids can also be estrogenic as they can be aromatized into estrogen-like metabolites that possess estrogenic activity.
InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1
Key:UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol cypionate (INN, USAN; Depo-Estradiol, Depofemin, Estradep, many others), or estradiol cipionate, is a synthetic ester, specifically the 3-cyclopentylpropanoyl ester, of the natural estrogen, estradiol. It was first introduced in 1952 by Upjohn in the United States, and has been in widespread use since. Estradiol cypionate is absorbed more slowly than estradiol itself, and for that reason, it can be administered less often. Compared to other commonly used estradiol esters, via the intramuscular route, estradiol cypionate was found to have the longest duration of action with a duration of ~11 days, while estradiol benzoate and estradiol valerate were found to last for 4–5 days and 7–8 days, respectively. M: ♀ FRS anat/phys/devp noco/cong/npls, sysi/epon proc/asst, drug (G1/G2B/G3CD) Note: Though not listed here, many anabolic steroids can also be estrogenic as they can be aromatized into estrogen-like metabolites that possess estrogenic activity.
Sustanon 250 is a trade name for an oil-based injectable blend of four esterized testosterone compounds: Sustanon 100 was similar, though with three esters. This smaller dose was usually for pediatric use. Sustanon 100 has not been produced since 2009. The different testosterone esters provide for different half lives. Esterization of the testosterone molecules provides for a sustained (but non-linear) release of testosterone from the injection depot into the blood plasma. While the intention of the mixed testosterone esters in Sustanon is to provide more stable serum testosterone levels, a single long-ester testosterone, such as testosterone cypionate or testosterone enanthate, may actually provide more stable serum testosterone levels. It is the preferred method of testosterone replacement in the UK as detailed in the British National Formulary.][ In the United Kingdom, there was a brief shortage of Sustanon 250 during late 2011, due to licensing problems and a further shortage in mid-2012 (unresolved as of 29 June 2012) due to manufacturing problems. Sustanon is a fairly popular anabolic steroid product among bodybuilders and athletes for muscle building purposes as well as other reasons such as andropause.][
testosterone cypionate United States USD Testosterone Unit of alcohol Wine bottle ML/I Korski vodka Endocrine system Androgens Neuroendocrinology Hospitality Recreation Hospitality Recreation

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