Drostanolone

Drostanolone
Clinical data
Trade names	Drolban, Masteril, Masteron, others (all as drostanolone propionate)
Other names	Dromostanolone; 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 class	Androgen; Anabolic steroid
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
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	58-19-5 ;
PubChem CID	6011;
ChemSpider	5789 ;
UNII	7DR7H00HDT;
ChEMBL	ChEMBL1582 ;
CompTox Dashboard (EPA)	DTXSID6022971 ;
ECHA InfoCard	100.000.334
Chemical and physical data
Formula	C20H32O2
Molar mass	304.474 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:IKXILDNPCZPPRV-RFMGOVQKSA-N ;
	(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

v
t
e
Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication	Ratio^a
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

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]

Legal status

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

Potential side effects

Like other AAS, drostanolone can cause a variety of side effects, including:

Virilization: This refers to the development of masculine characteristics in women, such as deepening of the voice, increased body hair growth, and clitoral enlargement.
Acne: AAS can increase sebum production, leading to acne.
Hair loss: Drostanolone can accelerate male pattern baldness.
Cardiovascular issues: AAS can negatively affect cholesterol levels and increase the risk of cardiovascular disease.
Liver damage: Although drostanolone is not 17α-alkylated, high doses or prolonged use can still potentially damage the liver.
Mood swings: AAS can cause aggression, irritability, and mood swings.

Non-medical uses

Drostanolone is used by some bodybuilders and athletes to increase muscle mass and strength. It is often used during "cutting cycles" to help preserve muscle mass while losing body fat. However, the use of AAS for non-medical purposes is not recommended due to the potential for serious side effects.

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

^ 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.
^ ^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.
^ ^a ^b ^c ^d ^e ^f Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1.
^ ^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.
^ 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.
^ 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.
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3.
^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
^ 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.
^ Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
^ US 2908693, Ringold HJ, Rosenkranz G, issued 1959, assigned to Syntex SA
^ US 3118915, Ringold HJ, Rosenkranz G, issued 1964, assigned to Roche Palo Alto LLC
^ GB 1005896 US 3249627, issued 1966, assigned to Ormonoterapia Richter Spa