Chemical Component Summary | |
|---|---|
| Name | ISO-URSODEOXYCHOLIC ACID |
| Identifiers | (4R)-4-[(3S,5S,7S,8R,9S,10S,13R,14S,17R)-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 |
| Formula | C24 H40 O4 |
| Molecular Weight | 392.572 |
| Type | NON-POLYMER |
| Isomeric SMILES | C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@@H](C4)O)C)O)C |
| InChI | InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1 |
| InChIKey | RUDATBOHQWOJDD-DNMBCGTGSA-N |
Chemical Details | |
|---|---|
| Formal Charge | 0 |
| Atom Count | 68 |
| Chiral Atom Count | 10 |
| Bond Count | 71 |
| Aromatic Bond Count | 0 |
Drug Info: DrugBank
| DrugBank ID | DB01586? |
|---|---|
| Name | Ursodeoxycholic acid |
| Groups |
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| Description | Ursodeoxycholic acid (UDCA), also known as ursodiol, is a naturally-occurring bile acid that constitutes a minor fraction of the human bile acid pool.[A256272,A256277] UDCA has been used to treat liver disease for decades: its first use in traditional medicine dates back more than a hundred years.[A256267,A256463] UDCA was first characterized in the bile of the Chinese black bear and is formed by 7b-epimerization of [chenodeoxycholic acid], which is a primary bile acid.[A256272] Due to its hydrophilicity, UDCA is less toxic than [cholic acid] or [chenodeoxycholic acid].[A256272] UDCA was first approved by the FDA in 1987 for dissolution of gallstones and for primary biliary cirrhosis in 1996.[A256272] UDCA works by replacing the hydrophobic or more toxic bile acids from the bile acid pool.[A256272] |
| Synonyms |
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| Brand Names |
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| Indication | Ursodeoxycholic acid is indicated for the treatment of patients with primary biliary cholangitis.[L44627] It is used for the short-term treatment of radiolucent, noncalcified gallbladder stones in patients selected for elective cholecystectomy. It is also used to prevent gallstone formation in obese patients experiencing rapid weight loss.[L44793] |
| Categories |
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| ATC-Code | A05AA02 |
| CAS number | 128-13-2 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | MDSKYQCVKLNDGHFMPVLGFGTYAPAEVPKSKALEAVKLAIEAGFHHID... | unknown | inhibitor |
| Bile acid receptor | MVMQFQGLENPIQISPHCSCTPSGFFMEMMSMKPAKGVLTEQVAGPLGQN... | unknown | partial agonist |
| Cytochrome P450 3A Subfamily | MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI... | unknown | inducer |
| Bile salt export pump | MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL... | unknown | substrate,inhibitor,inducer |
| Solute carrier organic anion transporter family member 1A2 | MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ... | unknown | substrate,inhibitor,inducer |
| View More | |||
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison
T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS.
Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682
Related Resource References
| Resource Name | Reference |
|---|---|
| PubChem | 127601 |
| ChEMBL | CHEMBL1233687 |
| ChEBI | CHEBI:43419 |
| CCDC/CSD | NECPUG |
