Английская Википедия:Drostanolone
Шаблон:Short description Шаблон:Drugbox
Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.[1][2][3] An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron.[1][2][3][4] This has also been used non-medically for physique- or performance-enhancing purposes.[3]
Pharmacology
Pharmacodynamics
Шаблон:Relative androgenic to anabolic activity in animals
Like other AAS, drostanolone is an agonist of the androgen receptor (AR).[3] It is not a substrate for 5α-reductase and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of anabolic to androgenic activity.[3] As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[3] While no data are available on the progestogenic activity of drostanolone, it is thought to have low or no such activity similarly to other DHT derivatives.[3] Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.[3]
Chemistry
Drostanolone, also known as 2α-methyl-5α-dihydrotestosterone (2α-methyl-DHT) or as 2α-methyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and a derivative of DHT.[1][2][3] It is specifically DHT with a methyl group at the C2α position.[1][2][3]
History
Drostanolone and its ester drostanolone propionate were first described in 1959.[3][5] Drostanolone propionate was first introduced for medical use in 1961.[6]
Society and culture
Generic names
Drostanolone is the generic name of the drug and its Шаблон:Abbrlink, Шаблон:Abbrlink, and Шаблон:Abbrlink.[1][2] It has also been referred to as dromostanolone.[1][2]
Legal status
Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[7]
Synthesis
Bolazine is when react 2 eq. with hydrazine to give dimer
Treatment of DHT (androstan-17β-ol-3-one, stanolone) [521-18-6] (1) with methyl formate and the strong base sodium methoxide gives [4033-95-8] (2). The newly added formyl function in the product is shown in the enol form. Catalytic hydrogenation reduces that function to a methyl group (3). The addition of hydrogen from the bottom face of the molecule leads to the formation of β-methyl isomer where the methyl group occupies the higher-energy axial position. Strong base-induced equilibration of the methyl group leads to the formation of the sterically favoured equatorial α-methyl isomer, affording dromostanolone (4).
References
External links
Шаблон:Androgens and antiandrogens Шаблон:Androgen receptor modulators
- ↑ 1,0 1,1 1,2 1,3 1,4 1,5 Шаблон:Cite book
- ↑ 2,0 2,1 2,2 2,3 2,4 2,5 Шаблон:Cite book
- ↑ 3,00 3,01 3,02 3,03 3,04 3,05 3,06 3,07 3,08 3,09 3,10 Шаблон:Cite book
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite journal
- ↑ Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
- ↑ Шаблон:Cite patent
- ↑ Шаблон:Cite patent
- ↑ Шаблон:Cite patent Шаблон:Cite patent
