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Showing drug card for Ursodeoxycholic acid (DB01586)

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Version 2.5
Creation Date 2007-08-29 14:57:33
Update Date 2009-04-16 16:48:25
Primary Accession Number DB01586
Secondary Accession Number Not Available
Name Ursodeoxycholic acid
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Ursodeoxycholic acid is an epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.
Synonyms
  1. (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
  2. 3,7-Dihydroxycholan-24-oic acid
  3. 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid
  4. 3-alpha,7-beta-Dihydroxycholanic acid
  5. 3-alpha,7-beta-Dioxycholanic acid
  6. 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
  7. 5beta-Cholan-24-oic acid-3alpha,7beta-diol
  8. 7-beta-Hydroxylithocholic acid
  9. 7beta-Hydroxylithocholic acid
  10. Acide ursodesoxycholique [inn-french]
  11. Acido ursodeossicolico [italian]
  12. Acido ursodeoxicolico [inn-spanish]
  13. Acidum ursodeoxycholicum [inn-latin]
  14. Chenodeoxycholic acid
  15. Iso-ursodeoxycholic acid
  16. UDCS
  17. Ursodesoxycholic acid
  18. Ursodiol
Brand Names
  1. Actigall
  2. Antigall
  3. Arsacol
  4. Cholit-ursan
  5. Delursan
  6. Destolit
  7. Deursil
  8. Dom-ursodiol c
  9. Litursol
  10. Lyeton
  11. PHL-ursodiol c
  12. PMS-ursodiol c
  13. Peptarom
  14. Solutrat
  15. Ursacol
  16. Urso
  17. Urso 250
  18. Urso DS
  19. Urso forte
  20. Ursobilin
  21. Ursochol
  22. Ursodamor
  23. Ursofalk
  24. Ursolvan
Brand Mixtures Not Available
Chemical IUPAC Name (4R)-4-[(3R,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
Chemical Formula C24H40O4
Chemical Structure Structure
CAS Registry Number 128-13-2
InChI Identifier InChI=1/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/f/h27H
InChI Key RUDATBOHQWOJDD-QERVUZFQDS
KEGG Drug D00734 Link Image
KEGG Compound C07880 Link Image
PubChem Compound 31401 Link Image
PubChem Substance 7847799 Link Image
ChEBI ID 9907 Link Image
PharmGKB ID Not Available
HET ID IU5 Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02238984 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ursodiol Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 392.5720
Monoisotopic Molecular Weight 392.2927
State Solid
Melting Point 203 oC
Experimental Water Solubility 0.02 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 1.97e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.00 [RODA,A ET AL. (1990)] Source: PhysProp
Predicted LogP 3.01 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.30 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1IHI Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric 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]3CC[C@]12C
Canonical SMILES CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C
Drug Category
  • Cholagogues and Choleretics
ATC Codes
AHFS Codes
  • 56:14.00
Indication Used to treat gall stones non-surgically.
Pharmacology Ursodiol (also known as ursodeoxycholic acid) is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the colon, primary bile acids can be metabolized into secondary bile acids by intestinal bacteria. Primary and secondary bile acids help the body digest fats. Ursodeoxycholic acid helps regulate cholesterol by reducing the rate at which the intestine absorbs cholesterol molecules while breaking up micelles containing cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.
Mechanism of Action Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells.
Absorption Not Available
Toxicity Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. [PubMed Link Image]
  2. Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. [PubMed Link Image]
  3. Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. [PubMed Link Image]
  4. Drugs.com Link Image
  5. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Aldo-keto reductase family 1 member C2
Drug Target 1 [top]
Target 1 ID 686
Target 1 Name Aldo-keto reductase family 1 member C2
Target 1 Synonyms
  1. 3-alpha-HSD3
  2. Chlordecone reductase homolog HAKRD
  3. DD/BABP
  4. DD2
  5. Dihydrodiol dehydrogenase 2
  6. Dihydrodiol dehydrogenase/bile acid-binding protein
  7. EC 1.-.-.-
  8. EC 1.1.1.213
  9. EC 1.3.1.20
  10. Trans-1,2- dihydrobenzene-1,2-diol dehydrogenase
  11. Type III 3- alpha-hydroxysteroid dehydrogenase
Target 1 Gene Name AKR1C2
Target 1 Protein Sequence >Aldo-keto reductase family 1 member C2 
MDSKYQCVKLNDGHFMPVLGFGTYAPAEVPKSKALEAVKLAIEAGFHHIDSAHVYNNEEQ
VGLAIRSKIADGSVKREDIFYTSKLWSNSHRPELVRPALERSLKNLQLDYVDLYLIHFPV
SVKPGEEVIPKDENGKILFDTVDLCATWEAMEKCKDAGLAKSIGVSNFNHRLLEMILNKP
GLKYKPVCNQVECHPYFNQRKLLDFCKSKDIVLVAYSALGSHREEPWVDPNSPVLLEDPV
LCALAKKHKRTPALIALRYQLQRGVVVLAKSYNEQRIRQNVQVFEFQLTSEEMKAIDGLN
RNVRYLTLDIFAGPPNYPFSDEY
Target 1 Number of Residues 328
Target 1 Molecular Weight 36736
Target 1 Theoretical pI 7.55
Target 1 GO Classification
Function
catalytic activity
oxidoreductase activity
Process
Not Available
Component
Not Available
Target 1 General Function Involved in oxidoreductase activity
Target 1 Specific Function Works in concert with the 5alpha/5beta-steroid reductases to convert steroid hormones into the 3alpha/5alpha and 3alpha/5beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5alpha-DHT) to 5-alpha-androstane-3alpha,17beta-diol (3-alpha-diol)
Target 1 Pathways Not Available
Target 1 Reactions
  • androsterone + NAD(P)+ = 5alpha-androstane-3,17-dione + NAD(P)H + H+
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 531160 Link Image
Target 1 UniProtKB/Swiss-Prot ID P52895 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name AK1C2_HUMAN Link Image
Target 1 PDB ID 1IHI Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasm (Potential)
Target 1 Gene Sequence >972 bp 
ATGGATTCGAAATACCAGTGTGTGAAGCTGAATGATGGTCACTTCATGCCTGTCCTGGGA
TTTGGCACCTATGCGCCTGCAGAGGTTCCTAAAAGTAAAGCTCTAGAGGCCGTCAAATTG
GCAATAGAAGCCGGGTTCCACCATATTGATTCTGCACATGTTTACAATAATGAGGAGCAG
GTTGGACTGGCCATCCGAAGCAAGATTGCAGATGGCAGTGTGAAGAGAGAAGACATATTC
TACACTTCAAAGCTTTGGAGCAATTCCCATCGACCAGAGTTGGTCCGACCAGCCTTGGAA
AGGTCACTGAAAAATCTTCAATTGGACTATGTTGACCTCTATCTTATTCATTTTCCAGTG
TCTGTAAAGCCAGGTGAGGAAGTGATCCCAAAAGATGAAAATGGAAAAATACTATTTGAC
ACAGTGGATCTCTGTGCCACGTGGGAGGCCATGGAGAAGTGTAAAGATGCAGGATTGGCC
AAGTCCATCGGGGTGTCCAACTTCAACCACAGGCTGCTGGAGATGATCCTCAACAAGCCA
GGGCTCAAGTACAAGCCTGTCTGCAACCAGGTGGAATGTCATCCTTACTTCAACCAGAGA
AAACTGCTGGATTTCTGCAAGTCAAAAGACATTGTTCTGGTTGCCTATAGTGCTCTGGGA
TCCCATCGAGAAGAACCATGGGTGGACCCGAACTCCCCGGTGCTCTTGGAGGACCCAGTC
CTTTGTGCCTTGGCAAAAAAGCACAAGCGAACCCCAGCCCTGATTGCCCTGCGCTACCAG
CTGCAGCGTGGGGTTGTGGTCCTGGCCAAGAGCTACAATGAGCAGCGCATCAGACAGAAC
GTGCAGGTGTTTGAATTCCAGTTGACTTCAGAGGAGATGAAAGCCATAGATGGCCTAAAC
AGAAATGTGCGATATTTGACCCTTGATATTTTTGCTGGCCCCCCTAATTATCCATTTTCT
GATGAATATTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID AKR1C2 Link Image
Target 1 GenAtlas ID AKR1C2 Link Image
Target 1 HGNC ID HGNC:385 Link Image
Target 1 Chromosome Location 10
Target 1 Locus 10p15-p14
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Nishizawa M, Nakajima T, Yasuda K, Kanzaki H, Sasaguri Y, Watanabe K, Ito S: Close kinship of human 20alpha-hydroxysteroid dehydrogenase gene with three aldo-keto reductase genes. Genes Cells. 2000 Feb;5(2):111-25. [PubMed Link Image]
  2. Qin KN, Khanna M, Cheng KC: Structure of a gene coding for human dihydrodiol dehydrogenase/bile acid-binding protein. Gene. 1994 Nov 18;149(2):357-61. [PubMed Link Image]
  3. Ciaccio PJ, Tew KD: cDNA and deduced amino acid sequences of a human colon dihydrodiol dehydrogenase. Biochim Biophys Acta. 1994 Jun 28;1186(1-2):129-32. [PubMed Link Image]
  4. Qin KN, New MI, Cheng KC: Molecular cloning of multiple cDNAs encoding human enzymes structurally related to 3 alpha-hydroxysteroid dehydrogenase. J Steroid Biochem Mol Biol. 1993 Dec;46(6):673-9. [PubMed Link Image]
  5. Shiraishi H, Ishikura S, Matsuura K, Deyashiki Y, Ninomiya M, Sakai S, Hara A: Sequence of the cDNA of a human dihydrodiol dehydrogenase isoform (AKR1C2) and tissue distribution of its mRNA. Biochem J. 1998 Sep 1;334 ( Pt 2):399-405. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.