Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H40O5 |
| Molecular Weight | 408.5714 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
InChI
InChIKey=BHQCQFFYRZLCQQ-UTLSPDKDSA-N
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1
| Molecular Formula | C24H40O5 |
| Molecular Weight | 408.5714 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Ursocholic acid (UCA) is the 7 beta epimer of the naturally occurring primary bile acid, cholic acid. Cholic acid (CA) administration does not reduce biliary cholesterol saturation unless its 7 alpha dehydroxylation to deoxycholic acid (DCA) is prevented by concomitant antibiotic treatment. It was shown, that UCA caused diarrhoea and hypercholesterolemia, had only a modest effect on biliary cholesterol saturation and thus UCA was not able to replace ursodeoxycholic and chenodeoxycholic acid for medical treatment of gallstones. In addition, as discovered, during ursocholic acid therapy the synthesis of primary bile acids continued whereas the formation of secondary bile acids was greatly increase.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| FXR-activating ligands inhibit rabbit ASBT expression via FXR-SHP-FTF cascade. | 2005-01 |
|
| A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases. | 1999-05 |
|
| Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid. | 1997-06 |
|
| Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid. | 1992-04 |
|
| Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients. | 1990-07 |
|
| Effect of ursocholic acid on bile lipid secretion and composition. | 1986-04 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9177526
were fed ursocholic acid 900 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15591588
Caco-2 cells were treated with 10 μM hydrophobic bile acids DCA, CDCA, and CA, which activate FXR, and 10 μM ursocholic acid (UCA), which almost do not activate FXR, for 40 h. Neither UCA nor ursochenodeoxycholic acid (UDCA) significantly reduced luciferase activity in P2 with intact α-fetoprotein transcription factor (FTF) binding site.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
MLP1T05RBX
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| Record Status |
Validated (UNII)
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DTXSID301018756
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81240
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MLP1T05RBX
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122340
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SUB11390MIG
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2955-27-3
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |