Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H39O5.Na |
Molecular Weight | 430.5532 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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])C[C@H](O)[C@]12C)[C@H](C)CCC([O-])=O
InChI
InChIKey=NRHMKIHPTBHXPF-TUJRSCDTSA-M
InChI=1S/C24H40O5.Na/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26;/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29);/q;+1/p-1/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-;/m1./s1
DescriptionCurator's Comment: Description was created based on several sources, including https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm438572.htm
Curator's Comment: Description was created based on several sources, including https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm438572.htm
Cholic acid is a primary bile acid synthesized from cholesterol in the liver. Endogenous bile acids including cholic acid enhance bile flow and provide the physiologic feedback inhibition of bile acid synthesis. The mechanism of action of cholic acid has not been fully established; however, it is known that cholic acid and its conjugates are
endogenous ligands of the nuclear receptor, farnesoid X receptor (FXR). FXR regulates enzymes and transporters that are involved in
bile acid synthesis and in the enterohepatic circulation to maintain bile acid homeostasis under normal physiologic conditions. U.S. Food and Drug Administration approved Cholbam (cholic acid) capsules, the first FDA approved treatment for pediatric and adult patients with bile acid synthesis disorders due to single enzyme defects, and for patients with peroxisomal disorders (including Zellweger spectrum disorders).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2047 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CHOLBAM Approved UseCHOLBAM® (cholic acid) is a bile acid indicated for the treatment of Bile Acid Synthesis Disorders due to single enzyme defects (SEDs) and Adjunctive treatment of peroxisomal disorders (PDs) including Zellweger Spectrum Disorders in patients who exhibit manifestations of liver disease, steatorrhea or complications from decreased fat soluble vitamin absorption Launch Date2015 |
|||
Primary | CHOLBAM Approved UseCHOLBAM® (cholic acid) is a bile acid indicated for the treatment of Bile Acid Synthesis Disorders due to single enzyme defects (SEDs) and Adjunctive treatment of peroxisomal disorders (PDs) including Zellweger Spectrum Disorders in patients who exhibit manifestations of liver disease, steatorrhea or complications from decreased fat soluble vitamin absorption Launch Date2015 |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg/kg 1 times / day multiple, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: multiple Dose: 10 mg/kg, 1 times / day Sources: |
unhealthy, 19 - 36 years n = 31 Health Status: unhealthy Condition: single enzyme defects Age Group: 19 - 36 years Sex: M+F Population Size: 31 Sources: |
Disc. AE: Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (1 patient) Sources: |
61.5 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 61.5 mg/kg, 1 times / day Route: oral Route: multiple Dose: 61.5 mg/kg, 1 times / day Sources: Page: p. 58 |
unhealthy n = 1 Health Status: unhealthy Population Size: 1 Sources: Page: p. 58 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Peripheral neuropathy | 1 patient Disc. AE |
10 mg/kg 1 times / day multiple, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: multiple Dose: 10 mg/kg, 1 times / day Sources: |
unhealthy, 19 - 36 years n = 31 Health Status: unhealthy Condition: single enzyme defects Age Group: 19 - 36 years Sex: M+F Population Size: 31 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000ClinPharmR.pdf#page=34 Page: 34.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000ClinPharmR.pdf#page=34 Page: 34.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Differential modulation of cellular death and survival pathways by conjugated bile acids. | 2001 |
|
Characterization, stability and in-vivo distribution of asialofetuin glycopeptide incorporating DSPC/CHOL liposomes prepared by mild cholate incubation. | 2001 Apr |
|
Separation of neutral compounds by microemulsion electrokinetic chromatography: fundamental studies on selectivity. | 2001 Apr |
|
Non-obese diabetic (NOD) mice exhibit an increased cellular immune response to glycated-LDL but are resistant to high fat diet induced atherosclerosis. | 2001 Aug |
|
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon. | 2001 Aug 28 |
|
Rim1 and rabphilin-3 bind Rab3-GTP by composite determinants partially related through N-terminal alpha -helix motifs. | 2001 Aug 31 |
|
Ion conductors derived from cholic acid and spermine: importance of facial hydrophilicity on NA(+) transport and membrane selectivity. | 2001 Aug 8 |
|
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples. | 2001 Dec |
|
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial. | 2001 Dec |
|
Dietary cholate increases plasma levels of apolipoprotein B in mice by posttranscriptional mechanisms. | 2001 Dec |
|
Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids. | 2001 Dec 14 |
|
Mitochondrial medicine--molecular pathology of defective oxidative phosphorylation. | 2001 Jan |
|
Enzymatic synthesis of aliphatic beta-lactosides as mimic units of glycosphingolipids by use of Trichoderma reesei cellulase. | 2001 Jan 1 |
|
Stacking and separation of coproporphyrin isomers by acetonitrile-salt mixtures in micellar electrokinetic chromatography. | 2001 Jul |
|
Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants. | 2001 Jul |
|
Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. | 2001 Jul |
|
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV. | 2001 Jul |
|
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes. | 2001 Jul 15 |
|
The orphan nuclear receptor LRH-1 potentiates the sterol-mediated induction of the human CETP gene by liver X receptor. | 2001 Jul 6 |
|
Monitored selection of DNA-hybrids forming duplexes with capped terminal C:G base pairs. | 2001 Jul-Aug |
|
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon. | 2001 Jun |
|
Transcriptional regulation of the human sterol 27-hydroxylase gene (CYP27) and promoter mapping. | 2001 Jun |
|
Expression of sterol 12alpha-hydroxylase alters bile acid pool composition in primary rat hepatocytes and in vivo. | 2001 Jun |
|
Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradation. | 2001 Jun |
|
Characterization of the promoter region of the human peroxisomal multifunctional enzyme type 2 gene. | 2001 Jun 1 |
|
Molecular umbrella-assisted transport of glutathione across a phospholipid membrane. | 2001 Jun 13 |
|
Antiatherogenic effects of 17 beta-estradiol and 17 alpha-estradiol and its derivative J811 in cholesterol-fed rabbits with thyroid inhibition. | 2001 Mar |
|
[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 |
|
Structural consequences of metal complexation of cyclo[Pro-Phe-Phe-Ala-Xaa]2 decapeptides. | 2001 Mar 16 |
|
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases. | 2001 May |
|
Activities of cholic acid-derived antimicrobial agents against multidrug-resistant bacteria. | 2001 May |
|
Design and synthesis of novel chiral dendritic species derived from bile acids. | 2001 May 4 |
|
A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function. | 2001 Nov 1 |
|
Circular dichroism spectra of the achiral guest N-aryl-N-nitrosamines included in the crystal host matrices of cholic acid. | 2001 Nov 2 |
|
Efficient gene delivery via non-covalent complexes of folic acid and polyethylenimine. | 2001 Nov 9 |
|
Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin. | 2001 Oct |
|
In vitro excystation of Paragonimus heterotremus metacercariae. | 2001 Oct |
|
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones. | 2001 Oct |
|
Colonic transit influences deoxycholic acid kinetics. | 2001 Oct |
|
Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids. | 2001 Oct |
|
NMR diffusion spectroscopy as a measure of host-guest complex association constants and as a probe of complex size. | 2001 Oct 19 |
|
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. | 2001 Oct 19 |
|
Simultaneous detection of cholyl adenylate and coenzyme A thioester utilizing liquid chromatography/electrospray ionization mass spectrometry. | 2001 Sep |
|
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs. | 2001 Sep |
|
Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol). | 2001 Sep 11 |
|
Side chain hydroxylations in bile acid biosynthesis catalyzed by CYP3A are markedly up-regulated in Cyp27-/- mice but not in cerebrotendinous xanthomatosis. | 2001 Sep 14 |
|
Determination of bioactive diterpenoids from Andrographis paniculata by micellar electrokinetic chromatography. | 2001 Sep 28 |
|
Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes. | 2002 Feb |
Patents
Sample Use Guides
The recommended dosage of CHOLBAM (cholic acid) is 10 to 15 mg/kg administered orally once daily, or in two divided doses, in pediatric patients and in adults.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28125709
25 uM cholic acid significantly upregulated Δ4-3-oxosteroid 5β-reductase member D1 of the aldo-keto reductase family 1 (AKR1D1) expression in HepG2 cells
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID9033979
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
SUB13343MIG
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
206-643-5
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
2286239
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
NU3Y4CCH8Z
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
D020358
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
361-09-1
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
23668194
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
26711
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
Sodium cholate
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY | |||
|
100000080099
Created by
admin on Fri Dec 15 15:11:48 GMT 2023 , Edited by admin on Fri Dec 15 15:11:48 GMT 2023
|
PRIMARY |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD