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 |
---|---|---|---|---|
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 Date4.28198396E11 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
Sun Dec 18 19:49:58 UTC 2022
by
admin
on
Sun Dec 18 19:49:58 UTC 2022
|
Record UNII |
0GEI24LG0J
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
TARGET -> AGONIST | |||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
TARGET -> AGONIST |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
IN VITRO
MINOR
|
||
|
METABOLITE -> PARENT |
IN VITRO
MINOR
|
||
|
METABOLITE -> PARENT |
IN VITRO
|
||
|
PARENT -> METABOLITE |
BILE
|
||
|
METABOLITE -> PARENT |
IN VITRO
MAJOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
Biological Half-life | PHARMACOKINETIC |
|
|
|||