Metribolone

Metribolone
Clinical data


Routes of administration	Oral
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
Synonyms	Methyltrienolone, 17α-Methyltrenbolone; R-1881; RU-1881; NSC-92858; 17α-Methyl-19-nor-Δ^9,11-testosterone; 17α-Methylestra-4,9,11-trien-17β-ol-3-one
CAS Number	965-93-5^Y
PubChem CID	261000
IUPHAR/BPS	2857
ChemSpider	229099^N
UNII	2C323EGI97
KEGG	C14257^N
ChEBI	CHEBI:379896^N
ChEMBL	CHEMBL166444^Y
ECHA InfoCard	100.190.113
Chemical and physical data
Formula	C₁₉H₂₄O₂
Molar mass	284.393 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@]1(O)CC[C@]2([H])[C@]1(C)C=CC3=C4CCC(C=C4CC[C@@]23[H])=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^N Key:CCCIJQPRIXGQOE-XWSJACJDSA-N^N
^NY (what is this?)

Metribolone (INN) (developmental code names R-1881 (or RU-1881), NSC-92858), also known as methyltrienolone (or 17α-methyltrenbolone), as well as 17α-methyl-19-nor-Δ^9,11-testosterone or 17α-methyl-19-norandrosta-4,9,11-triene-17β-ol-3-one, is a highly potent, orally active, non-aromatizable anabolic-androgenic steroid (AAS) of the 19-nortestosterone and 17α-alkylated groups which was never marketed for clinical use but has been used in scientific research as a photoaffinity label for the androgen receptor (AR) and in AR ligand binding assays. It is the 17α-methylated derivative of trenbolone (trienolone), and is a similarly potent AAS, but has a high potential for hepatotoxicity similarly to other 17α-alkylated AAS. Metribolone binds with high affinity not only to the AR but also to the progesterone receptor (PR), and binds to the glucocorticoid receptor (GR) as well. It is said to be the most potent AAS.

Eleven members of the Greek national weightlifting team and 4 Greek track and field athletes tested positive with methyltrienolone prior to the 2008 Beijing Olympic Games.

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