Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H40O5 |
Molecular Weight | 408.5714 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
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])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI
InChIKey=BHQCQFFYRZLCQQ-OELDTZBJSA-N
InChI=1S/C24H40O5/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)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
Molecular Formula | C24H40O5 |
Molecular Weight | 408.5714 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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Target ID: CHEMBL2047 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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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 |
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Differential modulation of cellular death and survival pathways by conjugated bile acids. | 2001 |
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Influence of plasma triglyceride and plasma cholesterol levels on the clearance rate of fibrinogen. | 2001 |
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Characterization, stability and in-vivo distribution of asialofetuin glycopeptide incorporating DSPC/CHOL liposomes prepared by mild cholate incubation. | 2001 Apr |
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Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting. | 2001 Apr-Jul |
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On-line identification of trans- and cis-resveratrol by nonaqueous capillary electrophoresis/fluorescence spectroscopy at 77 K. | 2001 Aug |
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A double antibody sandwich enzyme-linked immunosorbent assay for the detection of Salmonella using biotinylated monoclonal antibodies. | 2001 Aug |
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1H- and (31)P-MR spectroscopy of primary and recurrent human brain tumors in vitro: malignancy-characteristic profiles of water soluble and lipophilic spectral components. | 2001 Aug |
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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 |
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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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Rim1 and rabphilin-3 bind Rab3-GTP by composite determinants partially related through N-terminal alpha -helix motifs. | 2001 Aug 31 |
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Ion conductors derived from cholic acid and spermine: importance of facial hydrophilicity on NA(+) transport and membrane selectivity. | 2001 Aug 8 |
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Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples. | 2001 Dec |
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Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial. | 2001 Dec |
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Dietary cholate increases plasma levels of apolipoprotein B in mice by posttranscriptional mechanisms. | 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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Cross-Linking study of cytochrome P450 1A2 in proteoliposomes. | 2001 Feb |
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Metabolic and functional properties of lactic acid bacteria in the gastro-intestinal ecosystem: a comparative in vitro study between bacteria of intestinal and fermented food origin. | 2001 Jul |
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Stacking and separation of coproporphyrin isomers by acetonitrile-salt mixtures in micellar electrokinetic chromatography. | 2001 Jul |
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Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants. | 2001 Jul |
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Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. | 2001 Jul |
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Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV. | 2001 Jul |
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Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes. | 2001 Jul 15 |
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Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles. | 2001 Jul 20 |
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Analysis of post-harvest fungicides by micellar electrokinetic chromatography. | 2001 Jul 27 |
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Transmembrane ion channels constructed of cholic acid derivatives. | 2001 Jul 27 |
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Monitored selection of DNA-hybrids forming duplexes with capped terminal C:G base pairs. | 2001 Jul-Aug |
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Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon. | 2001 Jun |
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Surfactant, but not the size of solid lipid nanoparticles (SLN) influences viability and cytokine production of macrophages. | 2001 Jun 19 |
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Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases. | 2001 May |
|
Controlled expansion of a molecular cavity in a steroid host compound. | 2001 May 16 |
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[Dietary cholesterol modifies pyroglutamyl aminopeptidase activity in mouse frontal cortex. Sexual differences]. | 2001 May 16-31 |
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A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function. | 2001 Nov 1 |
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Circular dichroism spectra of the achiral guest N-aryl-N-nitrosamines included in the crystal host matrices of cholic acid. | 2001 Nov 2 |
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Efficient gene delivery via non-covalent complexes of folic acid and polyethylenimine. | 2001 Nov 9 |
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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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Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin. | 2001 Oct |
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In vitro excystation of Paragonimus heterotremus metacercariae. | 2001 Oct |
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Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones. | 2001 Oct |
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Colonic transit influences deoxycholic acid kinetics. | 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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Evidence for an umbrella mechanism of bilayer transport. | 2001 Oct 10 |
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NMR diffusion spectroscopy as a measure of host-guest complex association constants and as a probe of complex size. | 2001 Oct 19 |
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Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. | 2001 Oct 19 |
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Potency of select statin drugs in a new mouse model of hyperlipidemia and atherosclerosis. | 2001 Oct 23 |
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Simultaneous detection of cholyl adenylate and coenzyme A thioester utilizing liquid chromatography/electrospray ionization mass spectrometry. | 2001 Sep |
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Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs. | 2001 Sep |
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Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol). | 2001 Sep 11 |
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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 |
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Determination of bioactive diterpenoids from Andrographis paniculata by micellar electrokinetic chromatography. | 2001 Sep 28 |
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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
Substance Class |
Chemical
Created
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Record UNII |
G1JO7801AE
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Record Status |
Validated (UNII)
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WHO-ATC |
A05AA03
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LOINC |
2080-0
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EU-Orphan Drug |
EU/3/09/683
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FDA ORPHAN DRUG |
170503
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EMA ASSESSMENT REPORTS |
KOLBAM (AUTHORIZED: METABOLISM, INBORN ERRORS)
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NDF-RT |
N0000175802
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NCI_THESAURUS |
C66913
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WHO-VATC |
QA05AA03
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LOINC |
30518-5
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DSLD |
353 (Number of products:3)
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1440856
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G1JO7801AE
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1133503
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m3480
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982
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CHOLIC ACID
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609
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ORPHACOL (AUTHORIZED:
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DB02659
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SUB13348MIG
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CHEMBL205596
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81-25-4
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BC-106
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G1JO7801AE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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LABELED -> NON-LABELED | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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LABELED -> NON-LABELED | |||
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TRANSPORTER -> INHIBITOR | |||
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LABELED -> NON-LABELED |
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TRANSPORTER -> INHIBITOR |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
IN VITRO
MINOR
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
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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