7-epi-Obeticholic Acid 3-Obeticholate Ester

Product Name 7-epi-Obeticholic Acid 3-Obeticholate Ester
Alternate Names Obeticholic Acid Impurities, Impurities of Obeticholic Acid
CAT No. CS-T-83206
CAS No. 1908444-28-9
Category Impurities
Stock IN-Stock
Mol. Wt. 823.24 g/mol
Mol. For. C₅₂H₈₆O₇
Hazardous This is a Hazardous Compound
COA View Sample COA
MSDS View Sample MSDS
Parent API Obeticholic Acid
Canonical Smiles CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)OC5CCC6(C7CCC8(C(C7C(C(C6C5)CC)O)CCC8C(C)CCC(=O)O)C)C)C)C)O
InchIKey CJNVDKNEYRWTNW-GBWJVFIXSA-N
Inchl InChI=1S/C52H86O7/c1-9-33-41-27-31(53)19-23-51(41,7)39-21-25-50(6)36(14-16-37(50)45(39)47(33)57)30(4)12-18-44(56)59-32-20-24-52(8)40-22-26-49(5)35(29(3)11-17-43(54)55)13-15-38(49)46(40)48(58)34(10-2)42(52)28-32/h29-42,45-48,53,57-58H,9-28H2,1-8H3,(H,54,55)/t29-,30-,31-,32-,33-,34-,35-,36-,37+,38+,39+,40+,41+,42+,45+,46+,47-,48-,49-,50-,51-,52-/m1/s1
IUPAC (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3-[(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]pentanoyl]oxy-7-hydroxy-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
Controlled No
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7-epi-Obeticholic Acid (7-ECA) is a synthetic bile acid derivative that has been shown to have potential therapeutic effects in the treatment of various liver diseases. It is a potent agonist of the farnesoid X receptor (FXR), a nuclear receptor that plays a critical role in regulating bile acid homeostasis, lipid metabolism, and inflammation. By activating FXR, 7-ECA can reduce the accumulation of toxic bile acids in the liver, improve insulin sensitivity, and reduce hepatic inflammation and fibrosis. One of the most promising derivatives of 7-ECA is the 3-Obeticholate Ester (3-OBE), which is a prodrug that is rapidly converted to 7-ECA in vivo. This esterification strategy enhances the bioavailability and pharmacokinetic properties of 7-ECA, allowing for more efficient delivery and targeted activation of FXR. Chemically, 7-ECA and 3-OBE belong to a class of compounds known as bile acids, which are natural detergents that play an essential role in the digestion and absorption of dietary fats and fat-soluble vitamins. Bile acids are synthesized in the liver from cholesterol and are secreted into the small intestine, where they emulsify fats and facilitate their absorption. Bile acids are also involved in the regulation of glucose and lipid metabolism, and their dysregulation has been implicated in the pathogenesis of various metabolic disorders, including non-alcoholic fatty liver disease (NAFLD), type 2 diabetes, and atherosclerosis. In conclusion, 7-ECA and its derivatives represent a promising class of compounds for the treatment of liver and metabolic diseases, and ongoing research is focused on elucidating their mechanisms of action and optimizing their therapeutic potential.

Related Compounds

Obeticholic Acid Impurity 9 | Obeticholic Acid Impurity 16 | Obeticholic Acid Impurity 22 | Glyco Obeticholic acid D7 | Obeticholic acid-[PEG]-n-Ester | Obeticholic Acid Impurity 13 | Obeticholic Acid Impurity 25 | Obeticholic Acid Hydroxy ester impurity | Obeticholic Acid Impurity 2 | Obeticholic Acid Impurity 21 | Obeticholic Acid D5 | Obeticholic Acid Impurity 11 | DL-Allantoin-5-13C,1-15N | Obeticholic Acid Impurity 10 | Obeticholic Acid Impurity 23 | Obeticholic Acid Impurity 6 | Obeticholic Acid Impurity 15 | Obeticholic acid D5 (Ethyl-1,2,2,2-d4) | Obeticholic acid D6 | Obeticholic Acid Impurity 5 | Obeticholic Acid Impurity 8 | Obeticholic acid methyl ester | Obeticholic Acid Impurity 7 | Obeticholic Acid Impurity 18 | Obeticholic Acid Impurity 20 | Obeticholic Acid Impurity 3 | Obeticholic Acid Impurity 19 | Obeticholic Acid Impurity 14 | Obeticholic Acid Impurity 4 | Obeticholic Acid Impurity 12 | Obeticholic Acid Impurity 1 | Obeticholic Acid Keto ester impurity |

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