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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O4
Molecular Weight 392.5729
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@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([H])(CC[C@]12C)[C@@]4(C)CC[C@]([H])(C[C@@]4([H])C[C@]3([H])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 392.5729
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

Chenodiol is the non-proprietary name for chenodeoxycholic acid, a naturally occurring human bile acid. It is a bitter-tasting white powder consisting of crystalline and amorphous particles freely soluble in methanol, acetone and acetic acid and practically insoluble in water. Chenodiol suppresses hepatic synthesis of both cholesterol and cholic acid, gradually replacing the latter and its metabolite, deoxycholic acid in an expanded bile acid pool. These actions contribute to biliary cholesterol desaturation and gradual dissolution of radiolucent cholesterol gallstones in the presence of a gall-bladder visualized by oral cholecystography. Bile acids may also bind the the bile acid receptor (FXR) which regulates the synthesis and transport of bile acids. Chenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. The likelihood of successful dissolution is far greater if the stones are floatable or small. For patients with nonfloatable stones, dissolution is less likely and added weight should be given to the risk that more emergent surgery might result form a delay due to unsuccessful treatment.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Chenodiol

Approved Use

Chenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. The likelihood of successful dissolution is far greater if the stones are floatable or small. For patients with nonfloatable stones, dissolution is less likely and added weight should be given to the risk that more emergent surgery might result form a delay due to unsuccessful treatment.

Launch Date

4.28198396E11
Primary
URSODIOL

Approved Use

Ursodiol

Launch Date

6.1655037E11
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
[Ursodeoxycholic acid as the main treatment of hepatobiliary diseases in children and teenagers].
2001
[Advances in the diagnosis and treatment of cholelithiasis].
2001
Ursodeoxycholic acid for the treatment of intrahepatic cholestasis of pregnancy.
2001 Apr
Primary biliary cirrhosis: from induction to destruction.
2001 Apr
Genetic disorders and molecular mechanisms in cholestatic liver disease--a clinical approach.
2001 Apr
Modulation of steady-state messenger RNA levels in the regenerating rat liver with bile acid feeding.
2001 Apr
Lichenoid eruptions due to ursodeoxycholic acid administration.
2001 Aug
Ursodiol prevents UC-associated CRC.
2001 Aug
Ursodeoxycholic acid causing exacerbation of dermatitis herpetiformis.
2001 Aug
Jaundice in non-cirrhotic primary biliary cirrhosis: the premature ductopenic variant.
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
Treatment of primary biliary cirrhosis.
2001 Jan-Dec
[Ursodeoxycholic acid and prevention of tacrine-induced hepatotoxicity: a pilot study].
2001 Jan-Feb
Ursodeoxycholic acid 'mechanisms of action and clinical use in hepatobiliary disorders'.
2001 Jul
Rapid progress of acute suppurative cholangitis to secondary sclerosing cholangitis sequentially followed-up by endoscopic retrograde cholangiography.
2001 Jul
A case of autoimmune hepatitis with a high titer of antimitochondrial antibody and normal gamma-globulinemia.
2001 Jul
Effect of bile acids on the proliferative activity and apoptosis of rat hepatocytes.
2001 Jun
Ofloxacin and ursodeoxycholic acid versus ursodeoxycholic acid alone to prevent occlusion of biliary stents: a prospective, randomized trial.
2001 Jun
Effect of bezafibrate in primary biliary cirrhosis: a pilot study.
2001 Jun
Alterations in tight junctions differ between primary biliary cirrhosis and primary sclerosing cholangitis.
2001 Jun
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
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.
2001 Jun 1
Ursodeoxycholic acid ameliorates ibuprofen-induced enteropathy in the rat.
2001 Mar
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid.
2001 Mar
[Effects of bile acid preparations on DNA biosynthesis, apoptosis, and necrosis in hepatocytes in vitro].
2001 Mar-Apr
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
Ursodeoxycholic acid for primary biliary cirrhosis: lesson for the future?
2001 May
Cytokine network in nonresponding chronic hepatitis C patients with genotype 1: role of triple therapy with interferon alpha, ribavirin, and ursodeoxycholate.
2001 May
Autoimmune liver disease. Current standards, future directions.
2001 May
High-dose ursodeoxycholic acid as a therapy for patients with primary sclerosing cholangitis.
2001 May
Isoursodeoxycholic acid: metabolism and therapeutic effects in primary biliary cirrhosis.
2001 May
Differences in the efficacy of ursodeoxycholic acid and bile acid metabolism between viral liver diseases and primary biliary cirrhosis.
2001 May
Effects of deoxycholic acid and its epimers on lipid peroxidation in isolated rat hepatocytes.
2001 May
MDR3 gene defect in adults with symptomatic intrahepatic and gallbladder cholesterol cholelithiasis.
2001 May
The wide spectrum of multidrug resistance 3 deficiency: from neonatal cholestasis to cirrhosis of adulthood.
2001 May
[Correction of metabolic disturbances in patients with cholestasis].
2001 May-Jun
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
The natural history of primary biliary cirrhosis: of genes and cooperation.
2001 Sep
Apolipoprotein E polymorphism, a marker of disease severity in primary biliary cirrhosis?
2001 Sep
Ursodeoxycholic acid and in vitro vasoactivity of hydrophobic bile acids.
2001 Sep
Geranylgeraniol, an intermediate product in mevalonate pathway, induces apoptotic cell death in human hepatoma cells: death receptor-independent activation of caspase-8 with down-regulation of Bcl-xL expression.
2001 Sep
Ten-year combination treatment with colchicine and ursodeoxycholic acid for primary biliary cirrhosis: a double-blind, placebo-controlled trial on symptomatic patients.
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 Fri Jun 25 20:57:46 UTC 2021
Edited
by admin
on Fri Jun 25 20:57:46 UTC 2021
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
URSODEOXYCHOLIC ACID [EP]
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 [WHO-DD]
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
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
URSODEOXYCHOLATE
Common Name English
Classification Tree Code System Code
NDF-RT N0000006801
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
FDA ORPHAN DRUG 242607
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
FDA ORPHAN DRUG 55390
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
LOINC 55159-8
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
FDA ORPHAN DRUG 191204
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
NDF-RT N0000175802
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
WHO-VATC QA05AA02
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
FDA ORPHAN DRUG 22187
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
EU-Orphan Drug EU/3/17/1878
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
FDA ORPHAN DRUG 636718
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
NCI_THESAURUS C2089
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
LIVERTOX 1011
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
WHO-ATC A05AA02
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
NCI_THESAURUS C29703
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
Code System Code Type Description
LACTMED
Ursodiol
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
PUBCHEM
31401
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
USP_CATALOG
1707806
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
204-879-3
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL1551
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
EPA CompTox
128-13-2
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
EVMPD
SUB11389MIG
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
MESH
D014580
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
FDA UNII
724L30Y2QR
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
CAS
128-13-2
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
RXCUI
62427
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
ALTERNATIVE
MERCK INDEX
M11344
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C1818
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
DRUG BANK
DB01586
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
IUPHAR
7104
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
DRUG CENTRAL
2797
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
INN
4920
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
RXCUI
11065
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
WIKIPEDIA
URSODIOL
Created by admin on Fri Jun 25 20:57:46 UTC 2021 , Edited by admin on Fri Jun 25 20:57:46 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
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When bound to bile acids, FXR repressed transcription of the gene encoding cholesterol 7α-hydroxylase, which is the rate-limiting enzyme in bile acid synthesis, and activated the gene encoding intestinal bile acid?binding protein, which is a candidate bile acid transporter.
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