Obeticholic Acid


Catalog No. size PriceQuantity
M6685-2 2mg solid $93
M6685-10 10mg solid $365

Description

Cas:459789-99-2

Product Information

Obeticholic Acid (INT747; 6-ECDCA) is a novel derivative of cholic acid which acts as a potent and selective FXR agonist displaying anticholeretic activity in an in vivo rat model of cholestasis. It inhibits vascular smooth muscle cell inflammation and migration as well as promotes adipocyte differentiation and regulates adipose cell function in vivo.

 

Chemical Formula: C26H44O4

 

Exact Mass: 420.32396

 

Molecular Weight: 420.63

 

Elemental Analysis: C, 74.24; H, 10.54; O, 15.21

 

Synonym: 

 

6-Ethylchenodeoxycholic acid;

Obeticholic acid;

INT 747

INT-747

INT747

6-ECDCA

Ocaliva

 

Chemical 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

 

InChi Key:

ZXERDUOLZKYMJM-ZWECCWDJSA-N

 

InChi Code: 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

 

Smiles Code:

C[C@@H]([C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)[C@H](CC)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)CCC(O)=O

 

 

Technical Data:

 

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

 

In Vitro

Obeticholic acid (INT-747) increases the expression of FXR-regulated genes in rat hepatocytes. Obeticholic acid (INT-747) reduces expression of liver JNK-1 and JNK-2. Obeticholic acid (INT-747) (256 μg/mL) shows complete inhibition of bacterial growth in all strains tested. Intestinal permeability remains unaffected after INT-747-addition to an IFN-γ-exposed intestinal epithelium of Caco-2 cells.

 

In Vivo

Obeticholic acid (INT-747) (10 mg/kg/day) completely reverted cholestasis induced by E217α. Administration of Obeticholic acid (INT-747) partially prevents the impairment in total bile acid output caused by E217α by increasing the relative abundance of β-MCA and TCDCA and TDCA. Obeticholic acid (INT-747)7 (10 mg/kg) and HS increases the pulmonary congestion in the animals. INT-747 does not improve renal pathology in the HS-fed animals. Obeticholic acid (INT-747) (5 mg/kg) significantly increases survival in BDL rats. Obeticholic acid (INT-747)-treated BDL rats exhibits a significant selective ileal increase in expression of pore-closing claudin-1. Ileal expression of ZO-1 is significantly up-regulated in INT-747-treated BDL rats.

 

 

References

 

  1. LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases;

 

  1. Fiorucci S, Di Giorgio C, Distrutti E. Obeticholic Acid: An Update of Its Pharmacological Activities in Liver Disorders. Handb Exp Pharmacol. 2019;256:283-295. doi: 10.1007/164_2019_227. Review. PubMed PMID: 31201552.

 

  1. Patient Group Input Submissions: Obeticholic Acid (Ocaliva): (Intercept Pharma Canada, Inc.): Indication: For the treatment of primary biliary cholangitis [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health;

 

  1. Pharmacoeconomic Review Report: Obeticholic Acid (Ocaliva): (Intercept Pharma Canada, Inc.): Indication: For the treatment of primary biliary cholangitis [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health;

 

  1. CADTH Canadian Drug Expert Committee Recommendation: Obeticholic Acid (Ocaliva — Intercept Pharmaceuticals Canada): Indication: Primary biliary cholangitis [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health;

 

Products are for research use only. Not for human use.

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