Obeticholic acid

Obeticholic acid
Clinical data
Trade namesOcaliva
Other names6α-ethyl-chenodeoxycholic acid; INT-747
AHFS/Drugs.comMonograph
MedlinePlusa616033
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Identifiers
  • (3α,5β,6α,7α)-6-Ethyl-3,7-dihydroxycholan-24-oic acid
    OR
    (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.238.318 Edit this at Wikidata
Chemical and physical data
FormulaC26H44O4
Molar mass420.634 g·mol−1
3D model (JSmol)
Melting point108–110 °C (226–230 °F) [4]
  • 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
  • InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
  • Key:ZXERDUOLZKYMJM-ZWECCWDJSA-N

Obeticholic acid (OCA), sold under the brand name Ocaliva, is a semi-synthetic bile acid analogue which has the chemical structure 6α-ethyl-chenodeoxycholic acid. It is used as a medication used to treat primary biliary cholangitis. Intercept Pharmaceuticals Inc. hold the worldwide rights to develop OCA outside Japan and China, where it is licensed to Dainippon Sumitomo Pharma.[5]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ "Liver disease". Health Canada. 9 May 2018. Retrieved 13 April 2024.
  3. ^ "Ocaliva EPAR". European Medicines Agency. 27 July 2010. Retrieved 12 July 2024.
  4. ^ Gioiello A, Macchiarulo A, Carotti A, Filipponi P, Costantino G, Rizzo G, et al. (April 2011). "Extending SAR of bile acids as FXR ligands: discovery of 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine". Bioorganic & Medicinal Chemistry. 19 (8): 2650–2658. doi:10.1016/j.bmc.2011.03.004. PMID 21459580.{{cite journal}}: CS1 maint: overridden setting (link)
  5. ^ "A $4 Billion Surprise for 45-Person Biotech". The Wall Street Journal. Retrieved 10 January 2014.