Obeticholic acid

Base Information

• Chemical Name: Obeticholic acid
• CAS No.: 459789-99-2
• Molecular Formula: C26H44O4
• Molecular Weight: 420.63
• Hs Code.: 2918199890
• European Community (EC) Number: 810-245-2
• UNII: 0462Z4S4OZ
• DSSTox Substance ID: DTXSID20196671
• Nikkaji Number: J2.007.345D
• Wikipedia: Obeticholic_acid
• Wikidata: Q15708271
• NCI Thesaurus Code: C80837
• RXCUI: 1798288
• Pharos Ligand ID: LAT554DATTNC
• Metabolomics Workbench ID: 149608
• ChEMBL ID: CHEMBL566315
• Mol file: 459789-99-2.mol

Synonyms:6-ECDCA;6-ethyl chenodeoxycholic acid;6-ethyl-3,7-dihydroxycholan-24-oic acid;6-ethylchenodeoxycholic acid;6alpha-ethyl-3alpha,7alpha-dihydroxy-5beta-cholan-24-oic acid;6alpha-ethyl-chenodeoxycholic acid;6ECDCA;cholan-24-oic acid, 6-ethyl-3,7-dihydroxy-, (3alpha,5beta,6alpha,7alpha)-;DSP-1747;DSP1747;INT 747;INT-747;INT747;obeticholic acid;Ocaliva

Chemical Property of Obeticholic acid

Chemical Property:

• Vapor Pressure: 5.16E-15mmHg at 25°C
• Melting Point: 108-110 °C
• Refractive Index: 1.529
• Boiling Point: 562.9 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 308.3 °C
• PSA: 77.76000
• Density: 1.091 g/cm³
• LogP: 5.11400
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 25 mg/ml)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 420.32395988
• Heavy Atom Count: 30
• Complexity: 649

Purity/Quality:

98% ^*data from raw suppliers

6-Ethylchenodeoxycholic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Recent ClinicalTrials: Effect of Heavy Alcohol Consumption on Farnesoid X Receptor (FXR) Signaling
• Recent EU Clinical Trials: The effect of obeticholic acid on gut microbiota, gastric motility, accommodation, gastrointestinal peptide in healthy volunteers
• Recent NIPH Clinical Trials: A Randomized, Double-blind, Parallel-group, Placebo-controlled, Exploratory Study of DSP-1747 in Patients with Nonalcoholic Steatohepatitis
• Description: Obeticholic acid is a semi-synthetic bile acid analogue and acts as a farnesoid-X receptor (FXR) agonist. It is used for the treatment of primary biliary cholangitis. It is also under investigation for the treatment of other liver diseases,primary biliary cirrhosis, bile acid diarrhea and related disorders. Study has shown that it also has potential for treating nonalcoholicsteatohepatitis (NASH), and portal hypertension. Obeticholic acid takes effect through acting s the agonist of the farnesoid X receptor (FXR), which is the regulator of bile and cholesterol metabolism in the liver. Obeticholic acid is a potent and selective farnesoid X receptor agonist that promotes the flow of bile in the liver. The drug was approved by the USFDA for the treatment of the rare chronic liver disease primary biliary cholangitis (PBC) in combination with ursodeoxycholic acid (UDCA) in adults with inadequate response to UDCA or as a single agent therapy in adults unable to tolerate UDCA. Obeticholic acid was discovered at the Università de Perugia and developed by Intercept Pharmaceuticals. Obeticholic acid has also been granted orphan drug designation for the treatment of primary sclerosing cholangitis and primary biliary cirrhosis and has received breakthrough therapy designation for the treatment of patients with nonalcohol steatohepatitis (NASH) with liver fibrosis.
• Uses: 6-Ethylchenodeoxycholic Acid is a derivative of the bile acid Chenodeoxycholic Acid (C291900). 6-Ethylchenodeoxycholic Acid is a potent activator of the farnesoid X nuclear receptor which reduces liver fat and fibrosis in animal models of fatty liver disease.