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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

[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-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 No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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
PubMed

PubMed

TitleDatePubMed
Toxicity of chenodeoxycholic acid in the nonhuman primate.
1975 Jun
Identification of a nuclear receptor for bile acids.
1999 May 21
Pharmacological modifications of endogenous antioxidant enzymes with special reference to the effects of deprenyl: a possible antioxidant strategy.
1999 Nov
Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy.
2000 Mar
Extracorporeal shock wave lithotripsy of gallstones with oral dissolution. Results in course of ten years in Czech Republic in correlation to indication criteria.
2001
[Advances in the diagnosis and treatment of cholelithiasis].
2001
Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry.
2001 Jan
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
Ursodeoxycholic acid administration in patients with cholestasis of pregnancy: effects on primary bile acids in babies and mothers.
2001 Mar
Apoptotic activity of novel bile acid derivatives in human leukemic T cells through the activation of caspases.
2001 May
3beta-hydroxy-delta5 -C27-steroid dehydrogenase deficiency: diagnosis and treatment.
2001 Oct
Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids.
2001 Oct
Functional analysis of the transcriptional activity of the mouse phospholipid transfer protein gene.
2001 Oct 5
External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice.
2001 Sep
Cerebrotendinous xanthomatosis: 11-year treatment with chenodeoxycholic acid in five patients. An electrophysiological study.
2001 Sep 15
Cerebrotendinous xanthomatosis: a rare disease with diverse manifestations.
2002 Apr
Inhibition of the MAPK and PI3K pathways enhances UDCA-induced apoptosis in primary rodent hepatocytes.
2002 Apr
Conversion of 7 alpha-hydroxycholesterol to bile acid in human subjects: is there an alternate pathway favoring cholic acid synthesis?
2002 Feb
Differences in the regulation of the classical and the alternative pathway for bile acid synthesis in human liver. No coordinate regulation of CYP7A1 and CYP27A1.
2002 Jul 26
Two novel mutations in the sterol 27-hydroxylase gene causing cerebrotendinous xanthomatosis.
2002 Mar
The UDCA dosage deficit: a fate shared with CDCA.
2002 Mar
Farnesoid X receptor and bile salts are involved in transcriptional regulation of the gene encoding the human bile salt export pump.
2002 Mar
Unconjugated bile acids modulate adult and neonatal neutrophil chemotaxis induced in vitro by N-formyl-met-leu-phe-peptide.
2002 Mar
Relationship between asymptomatic hypercholanaemia of pregnancy and progesterone metabolism.
2002 May
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose range for Chenodiol is 13 to 16 mg/kg/day in two divided doses, morning and night, starting with 250 mg b.i.d. the first two weeks and increasing by 250 mg/day each week thereafter until the recommended or maximum tolerated dose is reached. If diarrhea occurs during dosage buildup or later in treatment, it usually can be controlled by temporary dosage adjustment until symptoms abate, after which the previous dosage usually is tolerated. Dosage less than 10 mg/kg usually is ineffective and may be associated with increased risk of cholecystectomy, so is not recommended.
Route of Administration: Oral
Hepatocytes were treated with Chenodiol at 10, 30, and 100 uM for 48 h, and RNA was extracted for real-time PCR analysis. Chenodiol markedly suppressed CYP7A1, the rate-limiting enzyme of bile acid synthesis, but only moderately (35%) down-regulated CYP8B1 at a high concentration of 100uM. Chenodiol increased the two major target genes of the farnesoid X receptor (FXR), namely the small heterodimer partner (SHP) by fourfold, and markedly induced fibroblast growth factor 19 (FGF19) over 100-fold.
Substance Class Chemical
Created
by admin
on Sun Dec 18 19:49:58 UTC 2022
Edited
by admin
on Sun Dec 18 19:49:58 UTC 2022
Record UNII
0GEI24LG0J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHENODIOL
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
3?,7?-Dihydroxy-5?-cholan-24-oic acid
Systematic Name English
CHENODEOXYCHOLIC ACID
EP   INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
CHENODEOXYCHOLIC ACID [EP MONOGRAPH]
Common Name English
NSC-657949
Code English
CHENODEOXYCHOLIC ACID [MART.]
Common Name English
URSODEOXYCHOLIC ACID IMPURITY A [EP IMPURITY]
Common Name English
CHENODIOL [MI]
Common Name English
CHENODEOXYCHOLATE
Common Name English
CHENODIOL [USAN]
Common Name English
NSC-757798
Code English
ANTHROPODESOXYCHOLIC ACID
Common Name English
CHENODIOL [VANDF]
Common Name English
Chenodeoxycholic acid [WHO-DD]
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
CHENODIOL [ORANGE BOOK]
Common Name English
CHOLAN-24-OIC ACID, 3,7-DIHYDROXY-, (3.ALPHA.,5.BETA.,7.ALPHA.)
Common Name English
CHENODEOXYCHOLIC ACID [EP IMPURITY]
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
Classification Tree Code System Code
FDA ORPHAN DRUG 300510
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
LOINC 30519-3
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
NCI_THESAURUS C66913
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
EU-Orphan Drug EU/3/14/1406
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
FDA ORPHAN DRUG 175303
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
LOINC 2065-1
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
FDA ORPHAN DRUG 3384
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
LIVERTOX NBK547907
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
FDA ORPHAN DRUG 235406
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
WHO-ATC A05AA01
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
WHO-VATC QA05AA01
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
Code System Code Type Description
CAS
474-25-9
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
FDA UNII
0GEI24LG0J
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
CHEBI
36234
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
IUPHAR
608
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
PUBCHEM
10133
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
DRUG CENTRAL
4361
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
WIKIPEDIA
CHENODEOXYCHOLIC ACID
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
DRUG BANK
DB06777
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
DAILYMED
0GEI24LG0J
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
ChEMBL
CHEMBL240597
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
MERCK INDEX
M3324
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY Merck Index
RXCUI
42588
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
ALTERNATIVE
MESH
D002635
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
INN
4391
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
EPA CompTox
DTXSID2020260
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
NSC
757798
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
EVMPD
SUB07463MIG
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
NCI_THESAURUS
C65206
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
ECHA (EC/EINECS)
207-481-8
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
NSC
657949
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
CHEBI
16755
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
RXCUI
2323
Created by admin on Sun Dec 18 19:50:02 UTC 2022 , Edited by admin on Sun Dec 18 19:50:02 UTC 2022
PRIMARY
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TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
MINOR
SALT/SOLVATE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC