IU5

ISO-URSODEOXYCHOLIC ACID

Created:	1999-11-10
Last modified:	2011-06-04

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3 entries where IU5 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	68
Chiral Atom Count	10
Bond Count	71
Aromatic Bond Count	0

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Chemical Component Summary
Name	ISO-URSODEOXYCHOLIC ACID
Systematic Name (OpenEye OEToolkits)	(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

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)CCC(C4C3(C(C1C(C2(C(CC1O)CC(O)CC2)C)CC3)CC4)C)C
SMILES	CACTVS	3.341	C[CH](CCC(O)=O)[CH]1CC[CH]2[CH]3[CH](O)C[CH]4C[CH](O)CC[C]4(C)[CH]3CC[C]12C
SMILES	OpenEye OEToolkits	1.5.0	CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
Canonical SMILES	CACTVS	3.341	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]3CC[C@]12C
Canonical SMILES	OpenEye OEToolkits	1.5.0	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	1.03	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	InChI	1.03	RUDATBOHQWOJDD-DNMBCGTGSA-N

Drug Info: DrugBank

DrugBank ID	DB01586
Name	Ursodeoxycholic acid
Groups	approved investigational
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	Acide ursodesoxycholique (3α,5β,7β)-3,7-dihydroxycholan-24-oic acid 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid Acido ursodeoxicolico Acidum ursodeoxycholicum Ursodiol UDCA Ursodeoxycholate Ursodeoxycholic acid (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid Acido ursodeossicolico
Brand Names	Ursodiol 200 mg BAMBOO SALT Eunganggo Jook Yeom Ursodiol Tablets, 250 mg Dom-ursodiol C Pendo-ursodiol C Urso DS Urusa Actigall Ag-ursodiol Gln-ursodiol Ursodiol Tablets, 500 mg PMS-ursodiol C Ursodiol Urso Forte Ursodiol 400 mg Urso BAMBOO SALT Eunganggo Jook Yeom Toothpaste Nra-ursodiol Festal Plus Reltone 200 mg Reltone 400 mg Jamp-ursodiol Ursofalk Urso 250 Ursodiol C PMS-ursodiol PHL-ursodiol C Mint-ursodiol Novo-ursodiol
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	Alimentary Tract and Metabolism Bile Acid Preparations Bile acids and derivatives Bile Acids and Salts Bile and Liver Therapy Bile Therapy BSEP/ABCB11 inducers BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates Cholagogues and Choleretics Cholanes Cholelitholytic Agents Cholic Acids Cytochrome P-450 CYP3A Inducers Cytochrome P-450 Enzyme Inducers Fused-Ring Compounds Gastrointestinal Agents Steroids
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
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	inducer
Multidrug resistance-associated protein 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	inhibitor
Ileal sodium/bile acid cotransporter	MNDPNSCVDNATVCSGASCVVPESNFNNILSVVLSTVLTILLALVMFSMG...	unknown	inhibitor
Sodium/bile acid cotransporter	MEAHNASAPFNFTLPPNFGKRPTDLALSVILVFMLFFIMLSLGCTMEFSK...	unknown	substrate,inhibitor
Chloride anion exchanger	MIEPFGNQYIVARPVYSTNAFEENHKKTGRHHKTFLDHLKVCCSCSPQKA...	unknown	upregulator
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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