U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

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 9 / 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 (total daily dose)
Highest studied dose
Dose: 50 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources: Page: p.18
unhealthy, 37-65
n = 7
Health Status: unhealthy
Condition: Amyotrophic lateral sclerosis
Age Group: 37-65
Sex: M+F
Population Size: 7
Sources: Page: p.18
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: Page: p.4
unhealthy
n = 60
Health Status: unhealthy
Condition: Primary biliary cirrhosis
Population Size: 60
Sources: Page: p.4
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea (1.7%)
Sources: Page: p.4
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: Page: p.4
unhealthy
n = 60
Health Status: unhealthy
Condition: Primary biliary cirrhosis
Population Size: 60
Sources: Page: p.4
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
Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid.
2001
[Advances in the diagnosis and treatment of cholelithiasis].
2001
Ursodeoxycholic acid for the treatment of intrahepatic cholestasis of pregnancy.
2001 Apr
Prevention of colon cancer with ursodiol in ulcerative colitis.
2001 Aug
Ursodeoxycholic acid causing exacerbation of dermatitis herpetiformis.
2001 Aug
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
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
[Ursodeoxycholic acid and prevention of tacrine-induced hepatotoxicity: a pilot study].
2001 Jan-Feb
Rapid progress of acute suppurative cholangitis to secondary sclerosing cholangitis sequentially followed-up by endoscopic retrograde cholangiography.
2001 Jul
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
Low in vivo toxicity of a novel cisplatin-ursodeoxycholic derivative (Bamet-UD2) with enhanced cytostatic activity versus liver tumors.
2001 Jun
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.
2001 Jun 1
[3 beta-Hydroxysteroid-delta 5-oxidoreductase/isomerase deficiency].
2001 Mar
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid.
2001 Mar
Hypocholesterolemic effect of bile acid sulfonate analogs in hamsters.
2001 Mar
High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization.
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
Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis.
2001 May
MDR3 gene defect in adults with symptomatic intrahepatic and gallbladder cholesterol cholelithiasis.
2001 May
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450.
2001 Oct 19
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 Fri Dec 15 15:06:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:06:22 GMT 2023
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 [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
URSODIOL [INCI]
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
EP   INN   MART.   WHO-DD  
INN  
Official 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 Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
FDA ORPHAN DRUG 242607
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
FDA ORPHAN DRUG 55390
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
LOINC 55159-8
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
FDA ORPHAN DRUG 191204
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
NDF-RT N0000175802
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
WHO-VATC QA05AA02
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
FDA ORPHAN DRUG 22187
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
EU-Orphan Drug EU/3/17/1878
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
FDA ORPHAN DRUG 636718
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
NCI_THESAURUS C2089
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
LIVERTOX NBK548309
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
WHO-ATC A05AA02
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
NCI_THESAURUS C29703
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
Code System Code Type Description
LACTMED
Ursodiol
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
PUBCHEM
31401
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-879-3
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
SMS_ID
100000092107
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL1551
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID6023731
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
NSC
683769
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
EVMPD
SUB11389MIG
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
MESH
D014580
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
FDA UNII
724L30Y2QR
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
CAS
128-13-2
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
RXCUI
62427
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
ALTERNATIVE
MERCK INDEX
m11344
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY Merck Index
CHEBI
78604
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
NCI_THESAURUS
C1818
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
RS_ITEM_NUM
1707806
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
DAILYMED
724L30Y2QR
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
DRUG BANK
DB01586
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
IUPHAR
7104
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
USAN
Z-35
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
CHEBI
9907
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
DRUG CENTRAL
2797
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
INN
4920
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
RXCUI
11065
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
WIKIPEDIA
URSODIOL
Created by admin on Fri Dec 15 15:06:22 GMT 2023 , Edited by admin on Fri Dec 15 15:06:22 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
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AGONIST
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