Drostanolone

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]

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
IUPAC name
  • (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
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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
 NY (what is this?)  (verify)

Pharmacology

Pharmacodynamics
Androgenic vs. anabolic activity
of androgens/anabolic steroids
MedicationRatioa
Testosterone~1:1
Androstanolone (DHT)~1:1
Methyltestosterone~1:1
Methandriol~1:1
Fluoxymesterone1:1–1:15
Metandienone1:1–1:8
Drostanolone1:3–1:4
Metenolone1:2–1:30
Oxymetholone1:2–1:9
Oxandrolone1:3–1:13
Stanozolol1:1–1:30
Nandrolone1:3–1:16
Ethylestrenol1:2–1:19
Norethandrolone1:1–1:20
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).[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
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.[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 INN, BAN, and DCF.[1][2] It has also been referred to as dromostanolone.[1][2]

Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[7]

References
  1. 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.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1.
  3. Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4.
  4. 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.
  5. 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.
  6. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3.
  7. Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
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