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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O4
Molecular Weight 392.572
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URSODIOL

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

InChI

InChIKey=RUDATBOHQWOJDD-UZVSRGJWSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H40O4
Molecular Weight 392.572
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB01586

Ursodiol tablets, USP are bile acids indicated for the treatment of patients with primary biliary cirrhosis. Ursodiol (Ursodeoxycholic acid), a naturally occurring hydrophilic bile acid, derived from cholesterol, is present as a minor fraction of the total human bile acid pool. Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells. The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution. In addition to the replacement and displacement of toxic bile acids, other mechanisms of action include cytoprotection of the injured bile duct epithelial cells (cholangiocytes) against toxic effects of bile acids, inhibition of apotosis of hepatocytes, immunomodulatory effects, and stimulation of bile secretion by hepatocytes and cholangiocytes. 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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
URSODIOL

Approved Use

Ursodiol

Launch Date

1989
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.2 μM
15 mg/kg bw 1 times / day multiple, oral
dose: 15 mg/kg bw
route of administration: Oral
experiment type: MULTIPLE
co-administered:
URSODIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
49.8 μM × h
15 mg/kg bw 1 times / day multiple, oral
dose: 15 mg/kg bw
route of administration: Oral
experiment type: MULTIPLE
co-administered:
URSODIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
50 mg/kg 3 times / day multiple, oral
Highest studied dose
Dose: 50 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources:
unhealthy, 37-65
Health Status: unhealthy
Age Group: 37-65
Sex: M+F
Sources:
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea (1.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 1.7%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Inhibition 20 uM]
yes
no (co-administration study)
Comment: UDCA did not lead to detectable changes in midazolam pharmacokinetics
yes
weak (co-administration study)
Comment: UDCA modestly decreased digoxin disposition without
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The chemopreventive role of ursodeoxycholic acid in azoxymethane-treated rats: suppressive effects on enhanced group II phospholipase A2 expression in colonic tissue.
1998 Dec 25
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury.
1999 Aug
Ursodeoxycholic acid protects hepatocytes against oxidative injury via induction of antioxidants.
1999 Sep 24
Genotoxic polycyclic aromatic hydrocarbon ortho-quinones generated by aldo-keto reductases induce CYP1A1 via nuclear translocation of the aryl hydrocarbon receptor.
2000 Feb 15
Ursodeoxycholic acid (UDCA) for the treatment of amoxycillin-clavulanate potassium (Augmentin)-induced intra-hepatic cholestasis: report of two cases.
2000 Mar
Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid.
2001
Treatment of nonalcoholic fatty liver: present and emerging therapies.
2001
[Experience in treatment of chronic toxic hepatitis by ursodeoxicholic acid].
2001
Primary sclerosing cholangitis.
2001 Apr
Prevention of colon cancer with ursodiol in ulcerative colitis.
2001 Aug
Stimulation of ATP secretion in the liver by therapeutic bile acids.
2001 Aug 15
Micronuclei induction, cell cycle delay and apoptosis as markers of cellular stress caused by ursodeoxycholic acid in human lymphocytes.
2001 Aug 22
Crystal structure of human type III 3alpha-hydroxysteroid dehydrogenase/bile acid binding protein complexed with NADP(+) and ursodeoxycholate.
2001 Aug 28
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Functional modulation of the glucocorticoid receptor and suppression of NF-kappaB-dependent transcription by ursodeoxycholic acid.
2001 Dec 14
Ursodeooxycholic acid for primary biliary cirrhosis.
2001 Feb
Changes in titers of antimitochondrial and antinuclear antibodies during the course of primary biliary cirrhosis.
2001 Feb
Management of drug-induced liver disease.
2001 Feb
Ursodeoxycholic acid complexation with 2-hydroxypropyl-beta-cyclodextrin increases ursodeoxycholic acid biliary excretion after single oral administration in rats.
2001 Feb
Clinical studies with silymarin: fibrosis progression is the end point.
2001 Feb
Novel bile acid derivatives induce apoptosis via a p53-independent pathway in human breast carcinoma cells.
2001 Feb 10
Long-term evaluation of extracorporeal shock-wave lithotripsy for cholesterol gallstones.
2001 Jan
Use of ursodeoxycholic acid in liver diseases.
2001 Jan
Chemoprevention in ulcerative colitis: narrowing the gap between clinical practice and research.
2001 Jan 16
Ursodiol use is associated with lower prevalence of colonic neoplasia in patients with ulcerative colitis and primary sclerosing cholangitis.
2001 Jan 16
Ursodeoxycholic acid 'mechanisms of action and clinical use in hepatobiliary disorders'.
2001 Jul
Prevention and treatment of veno-occlusive disease.
2001 Jul-Aug
Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradation.
2001 Jun
Low in vivo toxicity of a novel cisplatin-ursodeoxycholic derivative (Bamet-UD2) with enhanced cytostatic activity versus liver tumors.
2001 Jun
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid.
2001 Mar
Treatment of cholestasis and cholestatic disorders.
2001 Mar
Characterization of primary pure cholesterol hepatolithiasis: cholangioscopic and selective cholangiographic findings.
2001 Mar
Ursodeoxycholic acid administration in patients with cholestasis of pregnancy: effects on primary bile acids in babies and mothers.
2001 Mar
Hepatitis C virus infection with peripheral neuropathy is not always associated with cryoglobulinaemia.
2001 Mar
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.
2001 May
Synthetic bile acid derivatives induce nonapoptotic death of human retinal pigment epithelial cells.
2001 May
MDR3 gene defect in adults with symptomatic intrahepatic and gallbladder cholesterol cholelithiasis.
2001 May
A preliminary trial of high-dose ursodeoxycholic acid in primary sclerosing cholangitis.
2001 Oct
Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4.
2001 Oct 19
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450.
2001 Oct 19
Apolipoprotein E polymorphism, a marker of disease severity in primary biliary cirrhosis?
2001 Sep
Biliary excretion of tauroursodeoxycholate-3-sulfate in the rat.
2001 Sep
Patents

Sample Use Guides

13 to 15 mg/kg/day administered in two to four divided doses with food
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:37 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:37 GMT 2025
Record UNII
724L30Y2QR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
URSODIOL
INCI   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
INCI   USAN  
Official Name English
URSODEOXYCHOLIC ACID
EP   INN   MART.   WHO-DD  
INN  
Preferred Name English
URSODEOXYCHOLIC ACID [MART.]
Common Name English
NSC-683769
Code English
URSODIOL [USP MONOGRAPH]
Common Name English
URSODIOL [MI]
Common Name English
3.ALPHA.,7.BETA.-DIHYDROXY-5B-CHOLAN-24-OIC ACID
Common Name English
URSODEOXYCHOLIC ACID [EP IMPURITY]
Common Name English
URSODIOL [USAN]
Common Name English
URSO
Brand Name English
URSODESOXYCHOLIC ACID
Common Name English
URSODIOL [ORANGE BOOK]
Common Name English
URSODEOXYCHOLIC ACID [EP MONOGRAPH]
Common Name English
ACTIGALL
Common Name English
UDCA
Common Name English
URSODIOL [VANDF]
Common Name English
URSODEOXYCHOLIC ACID [JAN]
Common Name English
URSONORM
Brand Name English
ursodeoxycholic acid [INN]
Common Name English
CHOLAN-24-OIC ACID, 3,7-DIHYDROXY-, (3.ALPHA.,5.BETA.,7.BETA.)-
Common Name English
URSODIOL [USP-RS]
Common Name English
Ursodeoxycholic acid [WHO-DD]
Common Name English
URSODEOXYCHOLATE
Common Name English
Classification Tree Code System Code
NDF-RT N0000006801
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
FDA ORPHAN DRUG 242607
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
FDA ORPHAN DRUG 55390
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
LOINC 55159-8
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
FDA ORPHAN DRUG 191204
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
NDF-RT N0000175802
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
WHO-VATC QA05AA02
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
FDA ORPHAN DRUG 22187
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
EU-Orphan Drug EU/3/17/1878
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
FDA ORPHAN DRUG 636718
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
NCI_THESAURUS C2089
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
LIVERTOX NBK548309
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
WHO-ATC A05AA02
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
NCI_THESAURUS C29703
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
Code System Code Type Description
LACTMED
Ursodiol
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
PUBCHEM
31401
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-879-3
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
SMS_ID
100000092107
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
ChEMBL
CHEMBL1551
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023731
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
NSC
683769
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
EVMPD
SUB11389MIG
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
MESH
D014580
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
FDA UNII
724L30Y2QR
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
CAS
128-13-2
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
RXCUI
62427
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
ALTERNATIVE
MERCK INDEX
m11344
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY Merck Index
CHEBI
78604
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
NCI_THESAURUS
C1818
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
RS_ITEM_NUM
1707806
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
DAILYMED
724L30Y2QR
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
DRUG BANK
DB01586
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
IUPHAR
7104
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
USAN
Z-35
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
CHEBI
9907
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
DRUG CENTRAL
2797
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
INN
4920
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
RXCUI
11065
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
WIKIPEDIA
URSODIOL
Created by admin on Mon Mar 31 17:46:37 GMT 2025 , Edited by admin on Mon Mar 31 17:46:37 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
PARENT -> METABOLITE ACTIVE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
BILE
METABOLITE -> PARENT
BILE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY