Stenbolone
{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields = changed
| verifiedrevid = 444787792
| IUPAC_name = (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-2,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
| image = Stenbolone.svg
| width = 225px
| tradename =
| pregnancy_AU =
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| routes_of_administration = Intramuscular injection (as stenbolone acetate)
| class = Androgen; Anabolic steroid
| bioavailability =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 5197-58-0
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| PubChem = 234454
| IUPHAR_ligand =
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| ChemSpiderID_Ref =
| ChemSpiderID = 204491
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3Q6FKA848S
| KEGG =
| ChEBI = 34980
| ChEMBL =
| synonyms = 2-Methyl-5α-androst-1-en-17β-ol-3-one; 2-Methyl-δ1-4,5α-dihydrotestosterone; 2-Methyl-δ1-DHT; Deacetylanatrofin
| C=20 | H=30 | O=2
| SMILES = CC1=C[C@]2([C@@H](CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)CC1=O)C
| StdInChI_Ref =
| StdInChI = 1S/C20H30O2/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/h11,13-16,18,22H,4-10H2,1-3H3/t13-,14-,15-,16-,18-,19-,20-/m0/s1
| StdInChIKey_Ref =
| StdInChIKey = GYBGISLVORKLBN-YNZDMMAESA-N
}}
Stenbolone is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.{{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=RA1-PA263|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1–}}{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT301|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=301–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA962|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=962–}}{{cite book | vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA261|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=261–}} A C17β ester prodrug of stenbolone, stenbolone acetate, is used as an AAS for depot intramuscular injection under the brand names Anatrofin and Stenobolone.
Chemistry
{{See also|List of androgens/anabolic steroids}}
Stenbolone, also known as 2-methyl-δ1-4,5α-dihydrotestosterone (2-methyl-δ1-DHT) or as 2-methyl-5α-androst-1-en-17β-ol-3-one, is a synthetic androstane steroid and a derivative of DHT. It is closely related structurally to drostanolone (2-methyl-DHT), 1-testosterone (δ1-DHT), and methylstenbolone (17α-methylstenbolone).{{cite journal |vauthors=Rahnema CD, Crosnoe LE, Kim ED |title=Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem |journal=Andrology |volume=3 |issue=2 |pages=150–5 |year=2015 |pmid=25684733 |doi=10.1111/andr.307 |s2cid=6999218 |doi-access=free }}
Society and culture
=Generic names=
Stenbolone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}.