Obeticholic Acid

CAS No:
459789-99-2 Category:
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Product Details:

  • CAS No: 459789-99-2
  • AHFC code:
  • Synonyms: 6-ECDCA, 6-Ethylchenodeoxycholic acid, 6alpha-Ethyl-chenodeoxycholic acid, INT 747, INT-747, INT747, Obeticholic acid, UNII-0462Z4S4OZ
  • ATC Code:
  • Chemical Formula: C26H44O4
  • Molecular Weight:
  • Assay/Purity: Typically NLT 98%
  • DrugBank:
  • 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
  • InChl: 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
  • PubChem:
  • IUPAC: Cholan-24-oic acid, 6-ethyl-3,7-dihydroxy-, (3alpha,5beta,6alpha,7alpha)-

Additional Details

Indication:
Obeticholic Acid is indicated as a primary farnesoid X receptor agonist to treat chronic liver diseases, particularly Primary Biliary Cirrhosis. Other indications for Obeticholic Acid therapy include Primary Sclerosing Cholangitis and Bile Acid Diarrhea. Intercept Pharmaceuticals has attained orphan drug designation for Obeticholic Acid therapy in the United States and Europe for the treatment of Primary Biliary Cirrhosis.
Pharmacodynamics:
Obeticholic Acid is a semi-synthetic derivative of bile acid and works by adhering to a receptor in the liver, thus changing the metabolism of lipids in the body. As a natural agonist of the farnesoid X receptor, Obeticholic Acid acts as a nuclear hormone receptor which regulates lipid metabolism and glucose, thus decreasing hepatic steatosis and insulin resistance.
Mode of Action:
Obeticholic Acid’s mechanism of action is unique as it acts as a hepatoprotective agent against a wide range of chronic liver diseases.
Metabolism:
Obeticholic Acid In vitro acts as a powerful farnesoid X receptor agonist in HuH7 cells. In vivo Obeticholic Acid protects against acute necrosis, protects hepatocytes, reduces renal inflammation and oxidative stress and improves proteinuria.
Toxicity:
Obeticholic Acid has not shown toxicity and the main adverse effect noted by patients is mild itching.
General Reference:
Gastroenterology. 2013 Sep;145(3):574-82.e1. doi: 10.1053/j.gastro.2013.05.042. Epub 2013 May 30.European Association for the Study of the Liver (EASL) International Liver Congress 2014
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