5D5

2-{[(3alpha,5beta,7alpha,8alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid


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Chemical Component Summary

Name2-{[(3alpha,5beta,7alpha,8alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Identifiers2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-bis(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
FormulaC26 H45 N O6 S
Molecular Weight499.704
TypeNON-POLYMER
Isomeric SMILESC[C@H](CCC(=O)NCCS(=O)(=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
InChIInChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
InChIKeyBHTRKEVKTKCXOH-LBSADWJPSA-N

Chemical Details

Formal Charge0
Atom Count79
Chiral Atom Count10
Bond Count82
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB08834 
NameTauroursodeoxycholic acid
Groups
  • investigational
  • approved
DescriptionTauroursodeoxycholic acid, also known as ursodoxicoltaurine, is a highly hydrophilic tertiary bile acid [A249070] that is produced in humans at a low concentration.[A249070] It is a taurine conjugate of [ursodeoxycholic acid] [A249065] with comparable therapeutic efficacy and safety,[A249070] but a much higher hydrophilicity.[A249060] Normally, hydrophilic bile acids regulates hydrophobic bile acids and their cytotoxic effects. Tauroursodeoxycholic acid can reduce the absorption of cholesterol in the small intestine, thereby reducing the body's intake of dietary cholesterol and the body cholesterol content.[A249080] Tauroursodeoxycholic acid is currently used in Europe to treat and prevent gallstones as a bile acid derivative.[L17040] Due to a range of its molecular properties - namely its anti-apoptotic effects - tauroursodeoxycholic acid has been examined in inflammatory metabolic diseases and neurodegenerative diseases.[A249065,A249070]
Synonyms
  • TUDCA
  • Ursodeoxycholyltaurine
  • Tauroursodeoxycholic acid
  • Tauroursodesoxycholic acid
  • Tauroursodeoxycholic acid dihydrate
Brand Names
  • Albrioza
  • Relyvrio
IndicationTauroursodeoxycholic acid is used to prevent and treat gallstone formation.[L17040] Tauroursodeoxycholic acid is used in combination with [phenylbutyric acid] to treat amyotrophic lateral sclerosis (ALS) in adults.[L42105,L43473]
Categories
  • Bile Acids and Salts
  • Cholagogues and Choleretics
  • Cholanes
  • Cholic Acids
  • Gastrointestinal Agents
CAS number14605-22-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Integrin alpha-5MGSRTPESPLHAVQLRWGPRRRPPLLPLLLLLLPPPPRVGGFNLDAEAPA...unknownactivator
Cytochrome P450 3A1MDLLSALTLETWVLLAVVLVLLYGFGTRTHGLFKKQGIPGPKPLPFFGTV...unknowninducer
Cytochrome P450 3A2MDLLSALTLETWVLLAVILVLLYRLGTHRHGIFKKQGIPGPKPLPFLGTV...unknowninducer
Solute carrier organic anion transporter family member 1A2MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...unknownsubstrate
Cystine/glutamate transporterMVRKPVVSTISKGGYLQGNVNGRLPSLGNKEPPGQEKVQLKRKVTLLRGV...unknownsubstrate
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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

Related Resource References

Resource NameReference
PubChem 9848818
ChEMBL CHEMBL272427
ChEBI CHEBI:80774