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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

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
URSODIOL
Primary
Chenodiol
PubMed

PubMed

TitleDatePubMed
[Ursodeoxycholic acid as the main treatment of hepatobiliary diseases in children and teenagers].
2001
Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid.
2001
[Experience in treatment of chronic toxic hepatitis by ursodeoxicholic acid].
2001
Ursodeoxycholic acid for the treatment of intrahepatic cholestasis of pregnancy.
2001 Apr
Prevention of colon cancer with ursodiol in ulcerative colitis.
2001 Aug
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
No beneficial effects of transdermal nicotine in patients with primary sclerosing cholangitis: results of a randomized double-blind placebo-controlled cross-over study.
2001 Feb
The effect of ursodeoxycholic acid in children with prolonged hepatitis A virus infection that may be a trigger factor for autoimmune hepatitis.
2001 Feb
Consecutive occurrence of primary biliary cirrhosis and autoimmune hepatitis: a case report and review of the literature.
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
Long-term evaluation of extracorporeal shock-wave lithotripsy for cholesterol gallstones.
2001 Jan
Use of ursodeoxycholic acid in liver diseases.
2001 Jan
Treatment of primary biliary cirrhosis.
2001 Jan-Dec
Ursodeoxycholic acid 'mechanisms of action and clinical use in hepatobiliary disorders'.
2001 Jul
Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants.
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
Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
2001 Jul
Prevention and treatment of veno-occlusive disease.
2001 Jul-Aug
Effect of bile acids on the proliferative activity and apoptosis of rat hepatocytes.
2001 Jun
Effect of ursodeoxycholate in University of Wisconsin solution on long term preservation of rat livers.
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
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
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
[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
[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
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450.
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

In Vivo Use Guide
13 to 15 mg/kg/day administered in two to four divided doses with food
Route of Administration: Oral
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
URSOCHOL
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 [USP]
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
ACTIGALL
Common Name English
UDCA
Common Name English
URSODIOL [VANDF]
Common 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 Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
NDF-RT N0000175802
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
WHO-VATC QA05AA02
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
LIVERTOX 1011
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
WHO-ATC A05AA02
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
Code System Code Type Description
PUBCHEM
31401
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY SWITZERF
ECHA (EC/EINECS)
204-879-3
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
ChEMBL
CHEMBL1551
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
EPA CompTox
128-13-2
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
EVMPD
SUB11389MIG
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
MESH
D014580
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
CAS
128-13-2
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
RXCUI
62427
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
ALTERNATIVE
MERCK INDEX
M11344
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY Merck Index
LactMed
128-13-2
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
NCI_THESAURUS
C1818
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
DRUG BANK
DB01586
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
IUPHAR
7104
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
INN
4920
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
RXCUI
11065
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY
WIKIPEDIA
URSODIOL
Created by admin on Tue Mar 06 11:22:38 UTC 2018 , Edited by admin on Tue Mar 06 11:22:38 UTC 2018
PRIMARY