ursodiol

Also known as UDCA, ACG240, (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid, Urso, (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid, (3a,5b,7b)-3,7-dihydroxycholan-24-oic acid, (3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid, (3α,5β,7β)-3,7-dihydroxycholan-24-oic acid

chemical compound

Key facts

Trade names: Actigall, Urso, others
Other names: Ursodiol
Ahfs drugs com: Monograph
Medlineplus: a699047
License data: United States"}]]}'>US DailyMed : Ursodiol
Pregnancy category: Australia"}]]}'>AU : B3
Routes of administration: By mouth
Atc code: A05AA02 ( WHO )
Legal status: Australia"}]]}'>AU : S4 (Prescription only) Canada"}]]}'>CA : ℞-only United Kingdom"}]]}'>UK : POM (Prescription only) United States"}]]}'>US : ℞-only In general: ℞ (Prescription only)
Cas number: 128-13-2
Drugbank: DB01586
Unii: 724L30Y2QR
Kegg: D00734
Chebi: CHEBI:9907
Chembl: ChEMBL1551
Pdb ligand: IU5 ( PDBe , RCSB PDB )
Comptox dashboard u s environmental prot: DTXSID6023731
Echa infocard: 100.004.437

via Wikipedia infobox

Chemical data

Formula: C24H40O4
Molecular weight: 392.6 g/mol
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
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
InChIKey: RUDATBOHQWOJDD-UZVSRGJWSA-N
XLogP: 4.9
Polar surface area: 77.8 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

7,914 papers

Ursodiol for hepatobiliary disorders.Annals of internal medicine · 1994
Ursodiol in patients with parenteral nutrition-associated cholestasis.The Annals of pharmacotherapy · 2007
ALSUntangled no. 25: ursodiol.Amyotrophic lateral sclerosis & frontotemporal degeneration · 2014
Ursodiol Prescriptions Following Bariatric Surgery: National Prescribing Trends and Outcomes.Obesity surgery · 2023
Ursodiol: good drug makes good.Gastroenterology · 2003

via PubMed

Wikidata facts

Mass: 392.29266

Show 7 more facts

chemical formula: C₂₄H₄₀O₄
World Health Organisation international non-proprietary name: ursodeoxycholic acid
canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
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
defined daily dose: 0.75
Commons category: Ursodeoxycholic acid
melting point: 203

Sources (7)

via Wikidata · CC0

~8 min read

Article

Ursodeoxycholic acid (UDCA), also known as ursodiol, is a secondary bile acid, produced in humans and most other species from metabolism by intestinal bacteria. It is synthesized in the liver in some species, and was first identified in bile of bears of genus Ursus, from which its name derived. In purified form, it has been used to treat or prevent several diseases of the liver or bile ducts.

It is available as a generic medication.