Metribolone

Metribolone
Clinical data
Other names	Methyltrienolone, 17α-Methyltrenbolone; R1881; R-1881; RU-1881; NSC-92858; 17α-Methyl-19-nor-Δ9,11-testosterone; 17α-Methylestra-4,9,11-trien-17β-ol-3-one
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid; Progestogen
Identifiers
	IUPAC name (8S,13S,14S,17S)-17-Hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one;
CAS Number	965-93-5 ;
PubChem CID	261000;
IUPHAR/BPS	2857;
ChemSpider	229099 ;
UNII	2C323EGI97;
KEGG	C14257 ;
ChEBI	CHEBI:379896 ;
ChEMBL	ChEMBL166444 ;
CompTox Dashboard (EPA)	DTXSID8034162 ;
ECHA InfoCard	100.190.113
Chemical and physical data
Formula	C19H24O2
Molar mass	284.399 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@]1(CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C)O;
	InChI InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1 ; Key:CCCIJQPRIXGQOE-XWSJACJDSA-N ;
	(verify)

Metribolone (developmental code R1881, also known as methyltrienolone) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR.^[1]^[2]^[3] More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.^[2]^[4]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 654–. ISBN 978-1-4757-2085-3.
^ ^a ^b William Llewellyn's Anabolics. Molecular Nutrition LLC. 2011. pp. 546–. ISBN 978-0-9828280-1-4.
^ Brinkmann AO, Kuiper GG, de Boer W, Mulder E, Bolt J, van Steenbrugge GJ, van der Molen HJ (January 1986). "Characterization of androgen receptors after photoaffinity labelling with [3H]methyltrienolone (R1881)". Journal of Steroid Biochemistry. 24 (1): 245–249. doi:10.1016/0022-4731(86)90058-0. PMID 2422446.
^ Cite error: The named reference Brueggemeier2006 was invoked but never defined (see the help page).

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 654–. ISBN 978-1-4757-2085-3.

[Llewellyn2011-2] William Llewellyn's Anabolics. Molecular Nutrition LLC. 2011. pp. 546–. ISBN 978-0-9828280-1-4.

[pmid2422446-3] Brinkmann AO, Kuiper GG, de Boer W, Mulder E, Bolt J, van Steenbrugge GJ, van der Molen HJ (January 1986). "Characterization of androgen receptors after photoaffinity labelling with [3H]methyltrienolone (R1881)". Journal of Steroid Biochemistry. 24 (1): 245–249. doi:10.1016/0022-4731(86)90058-0. PMID 2422446.

[Brueggemeier2006-4] Cite error: The named reference Brueggemeier2006 was invoked but never defined (see the help page).

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