Structure via PubChem · Public domain (PubChem)
metribolone
Sign in to saveAlso known as R1881, Methyltrienolone, 17alpha-Methyltrienolone, 17-methyloestra-4,9,11-trien-3-one,17beta-ol, R1881 (synthetic androgen), 17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one
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. 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 wa
In the Vinony graph
Vinony's link graph records 979 inbound references to metribolone, and connects out to anabolic steroid, ligand and mometasone furoate.
It sits within the topics 3β-Hydroxysteroid dehydrogenase inhibitors, Abandoned drugs and Androgens.
Vinony links it to 9 Wikipedia language editions.
Chemical data
- Formula
- C19H24O2
- Molecular weight
- 284.4 g/mol
- IUPAC name
- (8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- SMILES
- C[C@@]1(CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C)O
- InChIKey
- CCCIJQPRIXGQOE-XWSJACJDSA-N
- XLogP
- 2.1
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
732 papers- Relative binding affinity at metribolone androgenic binding sites of various antiandrogenic agents.Arzneimittel-Forschung · 1987
- Androgen receptor activation reduces the endothelial cell proliferation through activating the cSrc/AKT/p38/ERK/NFκB-mediated pathway.The Journal of steroid biochemistry and molecular biology · 2019
- Antiandrogens: selective androgen receptor modulators.Molecular and cellular endocrinology · 2002
- The effects of steroid hormones on a human colon cancer cell line in vitro.Anticancer research · 1992
- Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography.Journal of medicinal chemistry · 1992
via PubMed
Wikidata facts
- Mass
- 284.178
Show 6 more facts
- chemical formula
- C₁₉H₂₄O₂
- canonical SMILES
- CC1(CCC2C1(C=CC3=C4CCC(=O)C=C4CCC23)C)O
- isomeric SMILES
- C[C@@]1(CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C)O
- World Health Organisation international non-proprietary name
- metribolone
- Commons category
- Methyltrienolone
- physically interacts with
- androgen receptor
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
12 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Doping in sports
- References
- External links
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. 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.
==Medical uses== Metribolone was never approved for medical use, a situation unlikely to change given its liver toxicity even at low doses. It was studied for the potential treatment of advanced breast cancer in women but development was abandoned.
Excerpted from Wikipedia’s “metribolone” article, available under the CC BY-SA 4.0 licence.