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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O4
Molecular Weight 392.572
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

1983
PubMed

PubMed

TitleDatePubMed
Toxicity of chenodeoxycholic acid in the rhesus monkey.
1975 Aug
Toxicity of chenodeoxycholic acid in the nonhuman primate.
1975 Jun
Extracorporeal shock wave lithotripsy of gallstones with oral dissolution. Results in course of ten years in Czech Republic in correlation to indication criteria.
2001
Differential modulation of cellular death and survival pathways by conjugated bile acids.
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
Enzyme immunoassay for conjugated 7alpha-hydroxy-3-oxo-4-cholenoic acid in human urine.
2001
[Advances in the diagnosis and treatment of cholelithiasis].
2001
Effects of bile salts and aliphatic ionic surfactants on human lymphocyte proliferation.
2001 Apr
Cerebrotendinous xanthomatosis.
2001 Aug
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Duodenal reflux induces cyclooxygenase-2 in the esophageal mucosa of rats: evidence for involvement of bile acids.
2001 Dec
Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids.
2001 Dec 14
Enhanced expression of the human multidrug resistance protein 3 by bile salt in human enterocytes. A transcriptional control of a plausible bile acid transporter.
2001 Dec 14
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.
2001 Jun
Expression of sterol 12alpha-hydroxylase alters bile acid pool composition in primary rat hepatocytes and in vivo.
2001 Jun
[3-oxo-delta 4-steroid 5 beta-reductase deficiency].
2001 Mar
[3 beta-Hydroxysteroid-delta 5-oxidoreductase/isomerase deficiency].
2001 Mar
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid.
2001 Mar
Hypocholesterolemic effect of bile acid sulfonate analogs in hamsters.
2001 Mar
The nuclear receptors FXR and LXRalpha: potential targets for the development of drugs affecting lipid metabolism and neoplastic diseases.
2001 Mar
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.
2001 May
Apoptotic activity of novel bile acid derivatives in human leukemic T cells through the activation of caspases.
2001 May
Green tea upregulates the low-density lipoprotein receptor through the sterol-regulated element binding Protein in HepG2 liver cells.
2001 Nov
Transcriptional regulation of the human sterol 12alpha-hydroxylase gene (CYP8B1): roles of heaptocyte nuclear factor 4alpha in mediating bile acid repression.
2001 Nov 9
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
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: 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
Guest-responsive fluorescence variations of gamma-cyclodextrins labeled with hetero-functionalized pyrene and tosyl moieties.
2002 Feb
Use of ursodeoxycholic acid in patients with liver disease.
2002 Feb
MALDI-TOF-MS analysis of droplets prepared in an electrodynamic balance: "wall-less" sample preparation.
2002 Feb 1
Demonstration of a direct stimulatory effect of bile salts on rat colonic epithelial cell proliferation.
2002 Jan
Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor.
2002 Jan 25
Bile salts modulate chronic ethanol-induced hepatotoxicity.
2002 Jan-Feb
Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor.
2002 Jul 19
The amino acid residues asparagine 354 and isoleucine 372 of human farnesoid X receptor confer the receptor with high sensitivity to chenodeoxycholate.
2002 Jul 19
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
Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling.
2002 Jul 5
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
Characterization of rat liver bile acid acyl glucuronosyltransferase.
2002 Mar
The proximal colonic motor response to rectal mechanical and chemical stimulation.
2002 Mar
[Treatment of cholestatic liver diseases].
2002 Mar 15
Relationship between asymptomatic hypercholanaemia of pregnancy and progesterone metabolism.
2002 May
A novel primary bile acid in the Shoebill stork and herons and its phylogenetic significance.
2002 May
A natural product that lowers cholesterol as an antagonist ligand for FXR.
2002 May 31
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 Sat Dec 16 17:08:41 GMT 2023
Edited
by admin
on Sat Dec 16 17:08:41 GMT 2023
Record UNII
0GEI24LG0J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHENODIOL
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
3α,7α-Dihydroxy-5β-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 Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
LOINC 30519-3
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
NCI_THESAURUS C66913
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
EU-Orphan Drug EU/3/14/1406
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
FDA ORPHAN DRUG 175303
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
LOINC 2065-1
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
FDA ORPHAN DRUG 3384
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
LIVERTOX NBK547907
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
FDA ORPHAN DRUG 235406
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
WHO-ATC A05AA01
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
WHO-VATC QA05AA01
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
Code System Code Type Description
CAS
474-25-9
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
FDA UNII
0GEI24LG0J
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
CHEBI
36234
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
IUPHAR
608
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
PUBCHEM
10133
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
DRUG CENTRAL
4361
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
WIKIPEDIA
CHENODEOXYCHOLIC ACID
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
DRUG BANK
DB06777
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
DAILYMED
0GEI24LG0J
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL240597
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
SMS_ID
100000092597
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
MERCK INDEX
m3324
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY Merck Index
RXCUI
42588
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
ALTERNATIVE
MESH
D002635
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
INN
4391
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID2020260
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
NSC
757798
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
EVMPD
SUB07463MIG
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
NCI_THESAURUS
C65206
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-481-8
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
NSC
657949
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
CHEBI
16755
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
RXCUI
2323
Created by admin on Sat Dec 16 17:08:43 GMT 2023 , Edited by admin on Sat Dec 16 17:08:43 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
TARGET -> AGONIST
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC