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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
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
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
A preliminary trial of high-dose ursodeoxycholic acid in primary sclerosing cholangitis.
2001 Oct
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
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
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:22:38 UTC 2018
Edited
by admin
on Tue Mar 06 11:22:38 UTC 2018
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
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
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
FECAL
PARENT -> METABOLITE ACTIVE
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
BILE
METABOLITE -> PARENT
BILE
Related Record Type Details
ACTIVE MOIETY