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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 CHENODIOL

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-BSWAIDMHSA-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
Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid.
2001
Differential modulation of cellular death and survival pathways by conjugated bile acids.
2001
Prevention of irinotecan (CPT-11)-induced diarrhea by oral alkalization combined with control of defecation in cancer patients.
2001 Apr 15
Prevention of colon cancer with ursodiol in ulcerative colitis.
2001 Aug
Lichenoid eruptions due to ursodeoxycholic acid administration.
2001 Aug
Crystal structure of human type III 3alpha-hydroxysteroid dehydrogenase/bile acid binding protein complexed with NADP(+) and ursodeoxycholate.
2001 Aug 28
Functional modulation of the glucocorticoid receptor and suppression of NF-kappaB-dependent transcription by ursodeoxycholic acid.
2001 Dec 14
Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids.
2001 Dec 14
Treatment of primary biliary cirrhosis.
2001 Jan-Dec
Ursodeoxycholic acid 'mechanisms of action and clinical use in hepatobiliary disorders'.
2001 Jul
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
[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
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:26:19 UTC 2018
Edited
by admin
on Tue Mar 06 10:26:19 UTC 2018
Record UNII
0GEI24LG0J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHENODIOL
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
3.ALPHA.,7.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OIC ACID
Systematic Name English
CHENODEOXYCHOLIC ACID
EP   INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
NSC-657949
Code English
CHENODEOXYCHOLIC ACID [MART.]
Common Name English
CHENODIOL [MI]
Common Name English
CHENODEOXYCHOLATE
Common Name English
CHENODIOL [USAN]
Common Name English
ANTHROPODESOXYCHOLIC ACID
Common Name English
CHENODEOXYCHOLIC ACID [EP]
Common Name English
CHENODIOL [VANDF]
Common Name English
CHOLANORM
Brand Name English
CHENODEOXYCHOLIC ACID [INN]
Common Name English
CHENOFALK
Brand Name English
CHENIX
Brand Name English
CHENOCOL
Brand Name English
CHENODEOXYCHOLIC ACID [VANDF]
Common Name English
CHENODIOL [ORANGE BOOK]
Common Name English
CHOLAN-24-OIC ACID, 3,7-DIHYDROXY-, (3.ALPHA.,5.BETA.,7.ALPHA.)
Common Name English
CHENODEOXYCHOLIC ACID [JAN]
Common Name English
CHENDOL
Brand Name English
GALLODESOXYCHOLIC ACID
Common Name English
FLUIBIL
Brand Name English
CHENOSSIL
Brand Name English
CHENODESOXYCHOLIC ACID
Common Name English
CHENIC ACID
Common Name English
ANTHROPODODESOXYCHOLIC ACID
Common Name English
ANTHROPODEOXYCHOLIC ACID
Common Name English
CHENODEOXYCHOLIC ACID [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 186
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
WHO-ATC A05AA01
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
WHO-VATC QA05AA01
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
Code System Code Type Description
CAS
474-25-9
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
IUPHAR
608
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
PUBCHEM
10133
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
CHENODEOXYCHOLIC ACID
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
DRUG BANK
DB06777
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
ChEMBL
CHEMBL240597
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
MERCK INDEX
M3324
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY Merck Index
RXCUI
42588
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
ALTERNATIVE
MESH
D002635
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
INN
4391
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
EPA CompTox
474-25-9
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
EVMPD
SUB07463MIG
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
NCI_THESAURUS
C65206
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
ECHA (EC/EINECS)
207-481-8
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
RXCUI
2323
Created by admin on Tue Mar 06 10:26:19 UTC 2018 , Edited by admin on Tue Mar 06 10:26:19 UTC 2018
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> AGONIST
TARGET -> AGONIST
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC