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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
10.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Chenodiol Approved UseChenodiol 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 Date1983 |
PubMed
Title | Date | PubMed |
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Toxicity of chenodeoxycholic acid in the rhesus monkey. | 1975 Aug |
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Toxicity of chenodeoxycholic acid in the nonhuman primate. | 1975 Jun |
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Extracorporeal shock wave lithotripsy of gallstones with oral dissolution. Results in course of ten years in Czech Republic in correlation to indication criteria. | 2001 |
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Differential modulation of cellular death and survival pathways by conjugated bile acids. | 2001 |
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Suppression of renal disease and mortality in the female NZB x NZW F1 mouse model of systemic lupus erythematosus (SLE) by chenodeoxycholic acid. | 2001 |
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Enzyme immunoassay for conjugated 7alpha-hydroxy-3-oxo-4-cholenoic acid in human urine. | 2001 |
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[Advances in the diagnosis and treatment of cholelithiasis]. | 2001 |
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Effects of bile salts and aliphatic ionic surfactants on human lymphocyte proliferation. | 2001 Apr |
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Cerebrotendinous xanthomatosis. | 2001 Aug |
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Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon. | 2001 Aug 28 |
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Duodenal reflux induces cyclooxygenase-2 in the esophageal mucosa of rats: evidence for involvement of bile acids. | 2001 Dec |
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Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids. | 2001 Dec 14 |
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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 |
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Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon. | 2001 Jun |
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Expression of sterol 12alpha-hydroxylase alters bile acid pool composition in primary rat hepatocytes and in vivo. | 2001 Jun |
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[3-oxo-delta 4-steroid 5 beta-reductase deficiency]. | 2001 Mar |
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[3 beta-Hydroxysteroid-delta 5-oxidoreductase/isomerase deficiency]. | 2001 Mar |
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Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid. | 2001 Mar |
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Hypocholesterolemic effect of bile acid sulfonate analogs in hamsters. | 2001 Mar |
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The nuclear receptors FXR and LXRalpha: potential targets for the development of drugs affecting lipid metabolism and neoplastic diseases. | 2001 Mar |
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Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases. | 2001 May |
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Apoptotic activity of novel bile acid derivatives in human leukemic T cells through the activation of caspases. | 2001 May |
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Green tea upregulates the low-density lipoprotein receptor through the sterol-regulated element binding Protein in HepG2 liver cells. | 2001 Nov |
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Transcriptional regulation of the human sterol 12alpha-hydroxylase gene (CYP8B1): roles of heaptocyte nuclear factor 4alpha in mediating bile acid repression. | 2001 Nov 9 |
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3beta-hydroxy-delta5 -C27-steroid dehydrogenase deficiency: diagnosis and treatment. | 2001 Oct |
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Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids. | 2001 Oct |
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External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice. | 2001 Sep |
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Cerebrotendinous xanthomatosis: a rare disease with diverse manifestations. | 2002 Apr |
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Inhibition of the MAPK and PI3K pathways enhances UDCA-induced apoptosis in primary rodent hepatocytes. | 2002 Apr |
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Conversion of 7 alpha-hydroxycholesterol to bile acid in human subjects: is there an alternate pathway favoring cholic acid synthesis? | 2002 Feb |
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Guest-responsive fluorescence variations of gamma-cyclodextrins labeled with hetero-functionalized pyrene and tosyl moieties. | 2002 Feb |
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Use of ursodeoxycholic acid in patients with liver disease. | 2002 Feb |
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MALDI-TOF-MS analysis of droplets prepared in an electrodynamic balance: "wall-less" sample preparation. | 2002 Feb 1 |
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Demonstration of a direct stimulatory effect of bile salts on rat colonic epithelial cell proliferation. | 2002 Jan |
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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 |
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Bile salts modulate chronic ethanol-induced hepatotoxicity. | 2002 Jan-Feb |
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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 |
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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 |
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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 |
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Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling. | 2002 Jul 5 |
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Two novel mutations in the sterol 27-hydroxylase gene causing cerebrotendinous xanthomatosis. | 2002 Mar |
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The UDCA dosage deficit: a fate shared with CDCA. | 2002 Mar |
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Farnesoid X receptor and bile salts are involved in transcriptional regulation of the gene encoding the human bile salt export pump. | 2002 Mar |
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Unconjugated bile acids modulate adult and neonatal neutrophil chemotaxis induced in vitro by N-formyl-met-leu-phe-peptide. | 2002 Mar |
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Characterization of rat liver bile acid acyl glucuronosyltransferase. | 2002 Mar |
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The proximal colonic motor response to rectal mechanical and chemical stimulation. | 2002 Mar |
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[Treatment of cholestatic liver diseases]. | 2002 Mar 15 |
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Relationship between asymptomatic hypercholanaemia of pregnancy and progesterone metabolism. | 2002 May |
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A novel primary bile acid in the Shoebill stork and herons and its phylogenetic significance. | 2002 May |
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A natural product that lowers cholesterol as an antagonist ligand for FXR. | 2002 May 31 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/chenodiol.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25055961
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
Edited
Sat Dec 16 17:08:41 GMT 2023
by
admin
on
Sat Dec 16 17:08:41 GMT 2023
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Record UNII |
0GEI24LG0J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
300510
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LOINC |
30519-3
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NCI_THESAURUS |
C66913
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EU-Orphan Drug |
EU/3/14/1406
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FDA ORPHAN DRUG |
175303
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LOINC |
2065-1
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FDA ORPHAN DRUG |
3384
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LIVERTOX |
NBK547907
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FDA ORPHAN DRUG |
235406
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WHO-ATC |
A05AA01
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WHO-VATC |
QA05AA01
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474-25-9
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0GEI24LG0J
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36234
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608
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10133
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4361
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CHENODEOXYCHOLIC ACID
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DB06777
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0GEI24LG0J
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CHEMBL240597
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100000092597
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m3324
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42588
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ALTERNATIVE | |||
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D002635
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4391
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DTXSID2020260
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757798
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SUB07463MIG
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C65206
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207-481-8
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657949
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16755
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2323
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TRANSPORTER -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST | |||
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN VITRO
MINOR
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PARENT -> METABOLITE |
BILE
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METABOLITE -> PARENT |
IN VITRO
MINOR
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
MAJOR
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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