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Drostanolone

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Drostanolone
Clinical data
Trade namesDrolban, Masteril, Masteron, others (all as drostanolone propionate)
Other namesDromostanolone; 2α-Methyl-4,5α-dihydrotestosterone; 2α-Methyl-DHT; 2α-Methyl-5α-androstan-17β-ol-3-one
Routes of
administration		Intramuscular injection (as drostanolone propionate)
Drug classAndrogen; Anabolic steroid
Legal status
Legal status
Identifiers
  • (2R,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy- 2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.334 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
  • C[C@@H]1C[C@]2([C@@H](CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)CC1=O)C
  • InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1 ☒N
  • Key:IKXILDNPCZPPRV-RFMGOVQKSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.[2][3][4] 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.[2][3][4][5] This has also been used non-medically for physique- or performance-enhancing purposes.[4]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Like other AAS, drostanolone is an agonist of the androgen receptor (AR).[4] 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.[4] As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[4] 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.[4] Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.[4]

Chemistry

See also: List of androgens/anabolic steroids

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.[2][3][4] It is specifically DHT with a methyl group at the C2α position.[2][3][4]

History

Drostanolone and its ester drostanolone propionate were first described in 1959.[4][6] Drostanolone propionate was first introduced for medical use in 1961.[7]

Society and culture

Generic names

Drostanolone is the generic name of the drug and its INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and DCFTooltip Dénomination Commune Française.[2][3] It has also been referred to as dromostanolone.[2][3]

Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[8]

Synthesis

Bolazine is when react 2 eq. with hydrazine to give dimer

Thieme Synthesis:[9][10][11][12][13]

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

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ a b c d e f Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 652–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1.
  4. ^ a b c d e f g h i j k Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4.
  5. ^ Bennett MB, Helman P, Palmer P (November 1975). "Hormonal therapy of breast cancer with special reference to Masteril therapy". South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde. 49 (49): 2036–40. PMID 1242823.
  6. ^ Ringold HJ, Batres E, Halpern O, Necoechea E (1959). "Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040. ISSN 0002-7863.
  7. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3.
  8. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  9. ^ Ringold HJ, Batres E, Halpern O, Necoechea E (January 1959). "Steroids. CV. 1 2-Methyl and 2-hydroxymethylene-androstane derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040.
  10. ^ Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
  11. ^ US 2908693, Ringold HJ, Rosenkranz G, issued 1959, assigned to Syntex SA 
  12. ^ US 3118915, Ringold HJ, Rosenkranz G, issued 1964, assigned to Roche Palo Alto LLC 
  13. ^ GB 1005896  US 3249627, issued 1966, assigned to Ormonoterapia Richter Spa 
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