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Other names | 17α-Vinyltestosterone; Ethenyltestosterone; 17α-Ethenyltestosterone; 17α-Vinylandrost-4-en-17β-ol-3-one; 17α-Hydroxypregna-4,20-dien-3-one |
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Formula | C21H30O2 |
Molar mass | 314.469 g·mol−1 |
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Vinyltestosterone (also known as 17α-vinyltestosterone, 17α-vinylandrost-4-en-17β-ol-3-one, and 17α-hydroxypregna-4,20-dien-3-one) is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. [1] [2] However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone (17α-vinyl-δ5(10)-19-nortestosterone), have been marketed. [3] They are used as progestins for female hormonal contraception, rather than as AAS. [3]
Vinyltestosterone is a relatively weak AAS. [2] [4] [5] In one study, it showed approximately one-third and one-fifth of the respective androgenic and anabolic activity of other AAS such as nandrolone (19-nortestosterone), methyltestosterone (17α-methyltestosterone), and ethyltestosterone (17α-ethyltestosterone) in castrated male rats, whereas ethisterone (17α-ethynyltestosterone) showed almost no androgenic and anabolic activity (only 1/20 the anabolic potency of vinyltestosterone). [4] Additionally, in women with metastatic breast cancer, vinyltestosterone was found to be ineffective in treating the disease (unlike other AAS such as testosterone propionate or fluoxymesterone) [6] and produced little or no virilization in the women at a dosage of 100 mg intramuscularly three times per week. [5] [7] [8]
Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.
Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.
Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.
Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and effectiveness for bulking cycles. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.
Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.
Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.
Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.
Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.
Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.
Methandriol, also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.
Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.
Propetandrol, or propethandrol, also known as 17α-ethyl-19-nortestosterone 3β-propionate or 17α-ethyl-19-nor-4-androstenediol 3β-propionate, as well as 17α-ethylestr-4-en-3β,17β-diol 3β-propionate, is a synthetic and orally active anabolic–androgenic steroid (AAS) and progestogen and a 17α-alkylated derivative of 19-nortestosterone. It is an androgen ester – specifically, the 3β-propionate ester of norethandrolone (17α-ethyl-19-nortestosterone).
Norvinisterone, sold under the brand names Neoprogestin and Nor-Progestelea, is a progestin and androgen/anabolic steroid (AAS) medication which was used in Europe but is now no longer marketed. It is taken by mouth.
Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.
A 17α-alkylated anabolic steroid is a synthetic anabolic–androgenic steroid (AAS) that features an alkyl group, specifically a methyl or ethyl group, at the C17α position. Unlike many other AAS, 17α-alkylated AAS are orally active and do not require intramuscular injection. However, they uniquely possess a high potential for hepatotoxicity, which simultaneously limits their use. In addition, some have a high risk of gynecomastia due to uniquely high estrogenic activity, although this does not apply to 17α-alkylated AAS that are also 4,5α-reduced or 19-demethylated. The prototypical example of a 17α-alkylated AAS is methyltestosterone (17α-methyltestosterone).
Ethyltestosterone, or 17α-ethyltestosterone, also known as 17α-ethylandrost-4-en-17β-ol-3-one or 17α-pregn-4-en-17-ol-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed. Like methyltestosterone, ethyltestosterone is the parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone, ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.
Methylhydroxynandrolone, also known as 4-hydroxy-17α-methyl-19-nortestosterone (HMNT), as well as 4,17β-dihydroxy-17α-methylestr-4-en-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of nandrolone (19-nortestosterone) which was never marketed. It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use. The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement". MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.
11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.
17α-Vinyltestosterone in large doses manifested weak myotropic and androgenic activities in castrated male rats (1) and proved to be ineffective in the therapy of patients with metastatic breast cancer, in whom it had little or no virilizing effect at a dosage level of 100 mg. intramuscularly three times a week (18).