Vinyltestosterone

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Vinyltestosterone
17a-vinyltestosterone structure.png
Clinical data
Other names17α-Vinyltestosterone; Ethenyltestosterone; 17α-Ethenyltestosterone; 17α-Vinylandrost-4-en-17β-ol-3-one; 17α-Hydroxypregna-4,20-dien-3-one
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-Ethenyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C21H30O2
Molar mass 314.469 g·mol−1
3D model (JSmol)
  • C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C=C)O)C
  • InChI=1S/C21H30O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h4,13,16-18,23H,1,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21-/m1/s1
  • Key:ILGPJZIKYMIGMU-SJFWLOONSA-N

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]

See also

Related Research Articles

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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.

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

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<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

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<span class="mw-page-title-main">Ethisterone</span> Chemical compound

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<span class="mw-page-title-main">Trestolone</span> Chemical compound

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<span class="mw-page-title-main">Metribolone</span> Chemical compound

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<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

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<span class="mw-page-title-main">Normethandrone</span> Chemical compound

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<span class="mw-page-title-main">Norvinisterone</span> Chemical compound

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.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

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<span class="mw-page-title-main">Ethyltestosterone</span> Synthetic anabolic steroid

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.

<span class="mw-page-title-main">Methylhydroxynandrolone</span> Chemical compound

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.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

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.

References

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  3. 1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887, 889. ISBN   978-1-4757-2085-3.
  4. 1 2 SAUNDERS FJ, DRILL VA (1956). "The myotrophic and androgenic effects of 17-ethyl-19-nortestosterone and related compounds". Endocrinology. 58 (5): 567–72. doi:10.1210/endo-58-5-567. PMID   13317831.
  5. 1 2 SCHEDL HP, DELEA C, BARTTER FC (1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". J. Clin. Endocrinol. Metab. 19 (8): 921–35. doi:10.1210/jcem-19-8-921. PMID   14442516. 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).
  6. Gregory Pincus; Erwin P. Vollmer (17 September 2013). Biological Activities of Steroids in Relation to Cancer: Proceedings of a Conference Sponsored by the Cancer Chemotherapy National Service Center, National Cancer Institute, National Institutes of Health, U. S. Department of Health, Education and Welfare. Elsevier Science. pp. 26–. ISBN   978-1-4832-7057-9.
  7. SEGALOFF A, GORDON DL, HORWITT BN, MURISON PJ, SCHLOSSER JV (1955). "Hormonal therapy in cancer of the breast. X. The effect of vinyltestosterone therapy on clinical course and hormonal excretion". Cancer. 8 (5): 903–5. doi:10.1002/1097-0142(1955)8:5<903::aid-cncr2820080509>3.0.co;2-u. PMID   13261042. S2CID   45406269.
  8. SCHEDL HP, DELEA C, BARTTER FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". J. Clin. Endocrinol. Metab. 19 (8): 921–35. doi:10.1210/jcem-19-8-921. PMID   14442516.