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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H39O4.Na
Molecular Weight 414.5538
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM CHENODEOXYCHOLATE

SMILES

[Na+].[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=WDFRNBJHDMUMBL-OICFXQLMSA-M
InChI=1S/C24H40O4.Na/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);/q;+1/p-1/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H39O4
Molecular Weight 391.5641
Charge -1
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
Effects of clofibrate in primary biliary cirrhosis hypercholesterolemia and gallstones.
1975 Oct
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
Anti-inflammatory effects of 5-aminosalicylic acid conjugates with chenodeoxycholic acid and ursodeoxycholic acid on carrageenan-induced colitis in guinea-pigs.
2001 Dec
Inducible microsomal prostaglandin E synthase is overexpressed in colorectal adenomas and cancer.
2001 Dec
Effect of bile acids on absorption of nitrendipine in healthy subjects.
2001 Dec
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
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
Green tea upregulates the low-density lipoprotein receptor through the sterol-regulated element binding Protein in HepG2 liver cells.
2001 Nov
Reduced activity of 11 beta-hydroxysteroid dehydrogenase in patients with cholestasis.
2001 Nov
Cerebrotendinous xanthomatosis.
2001 Nov 13
Bile acids regulate RANTES gene expression through its cognate NF-kappaB binding sites.
2001 Nov 16
Predominance of human versus rat phenotype in the metabolic pathways for bile acid synthesis by hybrid WIF-B9 cells.
2001 Nov 30
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
Acute effects of dietary fat composition on postprandial plasma bile acid and cholecystokinin concentrations in healthy premenopausal women.
2001 Oct
Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids.
2001 Oct
Effects of bile acids on the humoral immune response: a mechanistic approach.
2001 Oct 5
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].
2001 Sep 1
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
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
Interactions of combined bile acids on hepatocyte viability: cytoprotection or synergism.
2002 Feb 7
Demonstration of a direct stimulatory effect of bile salts on rat colonic epithelial cell proliferation.
2002 Jan
Induction of cyclooxygenase-2 by tumor promoters in transformed and cytochrome P450 2E1-expressing hepatocytes.
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 Wed Jul 05 22:45:35 UTC 2023
Edited
by admin
on Wed Jul 05 22:45:35 UTC 2023
Record UNII
6V4571KSKE
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM CHENODEOXYCHOLATE
Common Name English
CHENODEOXYCHOLIC ACID, SODIUM SALT
Common Name English
CHENODEOXYCHOLIC ACID SODIUM SALT
Common Name English
CHENODESOXYCHOLIC ACID SODIUM SALT
Common Name English
NSC-681066
Code English
SODIUM CHENODESOXYCHOLATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66913
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
Code System Code Type Description
FDA UNII
6V4571KSKE
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
PRIMARY
NCI_THESAURUS
C91034
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
PRIMARY
CAS
2646-38-0
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
PRIMARY
NSC
681066
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
PRIMARY
PUBCHEM
23696998
Created by admin on Wed Jul 05 22:45:35 UTC 2023 , Edited by admin on Wed Jul 05 22:45:35 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY