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			{{Short description|Chemical compound}}
	{{Drugbox
			{{Drugbox
	| IUPAC_name = (2''R'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy- 2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopentaphenanthren-3-one
			| Verifiedfields = changed
	| image = Drostanolone.png
			| Watchedfields = changed
	| CAS_number = 58-19-5
			| verifiedrevid = 376093236
	| CAS_supplemental =
			| IUPAC_name = (2''R'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy- 2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopentaphenanthren-3-one
	| ATC_prefix = none
			| image = Drostanolone Structural Formula V2.svg
	| ATC_suffix =
			| width = 225px
	| ATC_supplemental =
	| PubChem = 6011
			<!--Clinical data-->
	| DrugBank =
			| tradename = Drolban, Masteril, Masteron, others (all as ])
	| chemical_formula =
			| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	| C=20 | H=32 | O=2
			| pregnancy_US = <!-- A / B / C / D / X -->
	| molecular_weight = 304.46 g/mol
			| pregnancy_category =
	| smiles = CC1CC2(C(CCC3C2CCC4(C3CCC4O)C)CC1=O)C
			| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
	| bioavailability =
	| protein_bound =		| legal_BR = C5
			| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
	| metabolism =
			| legal_CA = Schedule IV
	| elimination_half-life =
			| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
	| excretion =
			| legal_US = Schedule III
	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			| legal_status =
	| pregnancy_US = <!-- A / B / C / D / X -->
			| routes_of_administration = ] (as ])
	| pregnancy_category=
			| class = ]; ]
	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
			<!--Pharmacokinetic data-->
	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
			| bioavailability =
	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	| legal_status =		| protein_bound =
			| metabolism =
	| routes_of_administration =
			| elimination_half-life =
			| excretion =
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number = 58-19-5
			| CAS_supplemental =
			| ATC_prefix =
			| ATC_suffix =
			| ATC_supplemental =
			| PubChem = 6011
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB00858
			| UNII_Ref = {{fdacite|changed|FDA}}
			| UNII = 7DR7H00HDT
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1582
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 5789
			| synonyms = Dromostanolone; 2α-Methyl-4,5α-dihydrotestosterone; 2α-Methyl-DHT; 2α-Methyl-5α-androstan-17β-ol-3-one
			<!--Chemical data-->
			| C=20 | H=32 | O=2
			| SMILES = C1C2((CC32CC4(3CC4O)C)CC1=O)C
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 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
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = IKXILDNPCZPPRV-RFMGOVQKSA-N
	}}		}}
	'''Drostanolone''' (]; also known as '''dromostanolone''' or '''Drolban''') is an anabolic steroid. Its main medical applications are to lower ] levels, and as an ] agent in the treatment of some cancers. It is most commonly marketed as the ester ] (trade name Masteron).
			'''Drostanolone''', or '''dromostanolone''', is an ] (AAS) of the ] (DHT) group which was never marketed.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA652|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=652–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA377|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=377–}}</ref><ref name="Llewellyn2011">{{cite book| first = William | last = Llewellyn | name-list-style = vanc |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT517|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=517–}}</ref> An ] ] of drostanolone, ], was formerly used in the treatment of ] in women under brand names such as Drolban, Masteril, and Masteron.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /><ref name="pmid1242823">{{cite journal | vauthors = Bennett MB, Helman P, Palmer P | title = Hormonal therapy of breast cancer with special reference to Masteril therapy | journal = South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde | volume = 49 | issue = 49 | pages = 2036–40 | date = November 1975 | pmid = 1242823 }}</ref> This has also been used non-medically for ]s.<ref name="Llewellyn2011" />
	Ringold, H. J.; Batres, E.; Halpern, O.; Necoechea, E.; J. Amer. Chem. Soc. 1959, 81, 427.
			==Pharmacology==
			===Pharmacodynamics===
			{{Relative androgenic to anabolic activity in animals}}
			Like other AAS, drostanolone is an ] of the ] (AR).<ref name="Llewellyn2011" /> It is not a substrate for ] and is a poor substrate for ] (3α-HSD), and therefore shows a high ratio of ] to ] activity.<ref name="Llewellyn2011" /> As a DHT derivative, drostanolone is not a ] for ] and hence cannot be aromatized into ]ic ]s.<ref name="Llewellyn2011" /> While no data are available on the ]ic activity of drostanolone, it is thought to have low or no such activity similarly to other DHT derivatives.<ref name="Llewellyn2011" /> Since the drug is not ], it is not known to cause ].<ref name="Llewellyn2011" />
			==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 ] ] ] and a ] of DHT.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is specifically DHT with a ] at the C2α position.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />
			==History==
			Drostanolone and its ester ] were first described in 1959.<ref name="Llewellyn2011" /><ref name="RingoldBatres1959">{{cite journal| vauthors = Ringold HJ, Batres E, Halpern O, Necoechea E |title=Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives|journal=Journal of the American Chemical Society|volume=81|issue=2|year=1959|pages=427–432|issn=0002-7863|doi=10.1021/ja01511a040}}</ref> Drostanolone propionate was first introduced for medical use in 1961.<ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1402|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1402–}}</ref>
			==Society and culture==
			===Generic names===
			''Drostanolone'' is the ] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|DCF|Dénomination Commune Française}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /> It has also been referred to as ''dromostanolone''.<ref name="Elks2014" /><ref name="IndexNominum2000" />
			===Legal status===
			Drostanolone, along with other AAS, is a ] ] in the ] under the ].<ref name="FFFLM2006">{{cite book| first = Steven B. | last = Karch | name-list-style = vanc |title=Drug Abuse Handbook, Second Edition|url=https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}</ref>
			==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==
			] is when react 2 eq. with hydrazine to give dimer
			Synthesis:<ref>{{cite journal | vauthors = Ringold HJ, Batres E, Halpern O, Necoechea E | title = Steroids. CV. 1 2-Methyl and 2-hydroxymethylene-androstane derivatives | journal = Journal of the American Chemical Society | date = January 1959 | volume = 81 | issue = 2 | pages = 427–432 | doi = 10.1021/ja01511a040 }}</ref><ref>Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.</ref><ref>{{cite patent | inventor = Ringold HJ, Rosenkranz G | country = US | number = 2908693 | gdate = 1959 | assign1 = Syntex SA }}</ref><ref>{{cite patent | inventor = Ringold HJ, Rosenkranz G | country = US | number = 3118915 | gdate = 1964 | assign1 = Roche Palo Alto LLC }}</ref><ref>{{cite patent | country = GB | number = 1005896 }} {{cite patent | country = US | number = 3249627 | gdate = 1966 | assign1 = Ormonoterapia Richter Spa }}</ref>]]
			Treatment of DHT (androstan-17β-ol-3-one, stanolone) (1) with methyl formate and the strong base sodium methoxide gives (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 ==
			{{Reflist}}
			== External links ==
	http://dx.doi.org/10.1021/ja01511a040
			* {{Webarchive|url=https://web.archive.org/web/20160926003251/http://anabolic.org/masteron-drostanolone-propionate/ |date=2016-09-26 }}
	{{Anabolic steroids}}
	]
			{{Androgens and antiandrogens}}
			{{Androgen receptor modulators}}
			]
	{{gastrointestinal-drug-stub}}
			]
			]
			]