Structure via PubChem · Public domain (PubChem)
obeticholic acid
Sign in to saveAlso known as 6-ECDCA, 6-Et CDCA, 6-ethylchenodeoxycholic acid, INT-747, OCA, Ocaliva®, 6-Ethyl-CDCA
chemical compound
Chemical data
- Formula
- C26H44O4
- Molecular weight
- 420.6 g/mol
- IUPAC name
- (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- SMILES
- CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O
- InChIKey
- ZXERDUOLZKYMJM-ZWECCWDJSA-N
- XLogP
- 5.7
- Polar surface area
- 77.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2016
- Admin. routes
- oral
- Indications
- biliary liver cirrhosis, liver disease, non-alcoholic fatty liver disease, Hepatitis, Alcoholic
via ChEMBL · EBI
Research
951 papers- Obeticholic Acid.2012
- Obeticholic acid for the treatment of non-alcoholic steatohepatitis: interim analysis from a multicentre, randomised, placebo-controlled phase 3 trial.Lancet (London, England) · 2019
- Obeticholic Acid for Primary Biliary Cholangitis.Biomedicines · 2022
- A Placebo-Controlled Trial of Obeticholic Acid in Primary Biliary Cholangitis.The New England journal of medicine · 2016
- FXR agonists for MASH therapy: Lessons and perspectives from obeticholic acid.Medicinal research reviews · 2024
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 420.324
- Has use
- medication
Show 7 more facts
- medical condition treated
- primary biliary cholangitis
- chemical formula
- C₂₆H₄₄O₄
- World Health Organisation international non-proprietary name
- 奥贝胆酸
- canonical SMILES
- CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)O
- isomeric SMILES
- CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O
- defined daily dose
- 10
- legal status (medicine)
- boxed warning
Sources (8)
via Wikidata · CC0