Methandriol

Methandriol
Clinical data
Trade names	Crestabolic, Cytobolin, Diandren, Madiol, Stenediol, Mestenediol
Other names	Metandriol; Methylandrostenediol; Methylandrostenediole; 17α-Methylandrost-5-ene-3β,17β-diol
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid
Identifiers
	IUPAC name (3S,8S,9R,10R,13S,14R,17S)-10,13,17-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	521-10-8 ;
PubChem CID	229021;
ChemSpider	199375 ;
UNII	5730Z864KG;
CompTox Dashboard (EPA)	DTXSID50878534 ;
ECHA InfoCard	100.007.548
Chemical and physical data
Formula	C20H32O2
Molar mass	304.474 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C)O;
	InChI InChI=1S/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h4,14-17,21-22H,5-12H2,1-3H3/t14-,15+,16-,17-,18-,19-,20-/m0/s1 ; Key:WRWBCPJQPDHXTJ-DTMQFJJTSA-N ;
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Methandriol (INNTooltip International Nonproprietary Name) (brand names Crestabolic, Cytobolin, Diandren, Madiol, Stenediol, Mestenediol), also known as methylandrostenediol, as well as 17α-methylandrost-5-ene-3β,17β-diol, is a synthetic, orally active androgen and anabolic steroid (AAS) which was developed by Organon and is used in both oral and injectable (as methandriol dipropionate, methandriol propionate, or methandriol bisenanthoyl acetate) formulations.^[1]^[2] It is a 17α-alkylated AAS and the 17α-methylated derivative of the endogenous androgen prohormone androstenediol.^[1]^[2]

History

Methandriol was first synthesized in 1935 along with methyltestosterone and mestanolone.^[3]^[4]

^ ^a ^b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 794–. ISBN 978-1-4757-2085-3.
^ ^a ^b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
^ Schänzer W (1996). "Metabolism of anabolic androgenic steroids". Clin. Chem. 42 (7): 1001–20. PMID 8674183.
^ Ruzicka, L.; Goldberg, M. W.; Rosenberg, H. R. (1935). "Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung". Helvetica Chimica Acta. 18 (1): 1487–1498. doi:10.1002/hlca.193501801203. ISSN 0018-019X.

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