CHOLIC ACID

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

Structure Search

SMILES

C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

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

HIDE SMILES / InChI

Molecular Formula	C24H40O5
Molecular Weight	408.5714
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750s000lbl.pdf
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).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bile acid receptor FXR 29 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25073467 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750s000lbl.pdf	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bile acid synthesis disorders 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750s000lbl.pdf	Primary		Approved 8583	CHOLBAM Approved Use CHOLBAM® (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 Date 2015
Peroxisomal disorders 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750s000lbl.pdf	Primary		Approved 8583	CHOLBAM Approved Use CHOLBAM® (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 Date 2015

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750lbl.pdf	unhealthy, 19 - 36 years Health Status: unhealthy Age Group: 19 - 36 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750lbl.pdf	Disc. AE: Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000MedR.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000MedR.pdf

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750lbl.pdf	unhealthy, 19 - 36 years Health Status: unhealthy Age Group: 19 - 36 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/205750lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	BSEP 63 ASBT 5

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ASBT 5	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000ClinPharmR.pdf#page=34 Page: 34.0	yes
BSEP 63	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/205750Orig1s000ClinPharmR.pdf#page=34 Page: 34.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16359	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16359
ChemicalBook	CB52741764	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB52741764
ChemicalBook	CB9263222	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9263222
eMolecules	29504030	https://www.emolecules.com/cgi-bin/more?vid=29504030
eMolecules	29541145	https://www.emolecules.com/cgi-bin/more?vid=29541145
eMolecules	30512922	https://www.emolecules.com/cgi-bin/more?vid=30512922
MolPort	MolPort-003-892-613	https://www.molport.com/shop/molecule-link/MolPort-003-892-613
ZINC	ZINC000006858022	http://zinc15.docking.org/substances/ZINC000006858022

PubMed

Title	Date	PubMed
Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes.	2002-02	11689242
Antagonism of the actions of peroxisome proliferator-activated receptor-alpha by bile acids.	2001-12-14	11606578
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.	2001-12	11709519
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.	2001-12	11709518
Dietary cholate increases plasma levels of apolipoprotein B in mice by posttranscriptional mechanisms.	2001-12	11606258
Efficient gene delivery via non-covalent complexes of folic acid and polyethylenimine.	2001-11-09	11689266
Transcriptional regulation of the human sterol 12alpha-hydroxylase gene (CYP8B1): roles of heaptocyte nuclear factor 4alpha in mediating bile acid repression.	2001-11-09	11535594
Circular dichroism spectra of the achiral guest N-aryl-N-nitrosamines included in the crystal host matrices of cholic acid.	2001-11-02	11681951
A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function.	2001-11-01	11673866
Potency of select statin drugs in a new mouse model of hyperlipidemia and atherosclerosis.	2001-10-23	11604260
NMR diffusion spectroscopy as a measure of host-guest complex association constants and as a probe of complex size.	2001-10-19	11597206
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450.	2001-10-19	11509573
Evidence for an umbrella mechanism of bilayer transport.	2001-10-10	11583569
Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin.	2001-10	11695848
In vitro excystation of Paragonimus heterotremus metacercariae.	2001-10	11695393
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.	2001-10	11680582
Colonic transit influences deoxycholic acid kinetics.	2001-10	11606495
Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids.	2001-10	11579204
Determination of bioactive diterpenoids from Andrographis paniculata by micellar electrokinetic chromatography.	2001-09-28	11681575
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.	2001-09-21	11563018
Side chain hydroxylations in bile acid biosynthesis catalyzed by CYP3A are markedly up-regulated in Cyp27-/- mice but not in cerebrotendinous xanthomatosis.	2001-09-14	11454857
Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol).	2001-09-11	11532566
Simultaneous detection of cholyl adenylate and coenzyme A thioester utilizing liquid chromatography/electrospray ionization mass spectrometry.	2001-09	11708055
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.	2001-09	11699836
Rim1 and rabphilin-3 bind Rab3-GTP by composite determinants partially related through N-terminal alpha -helix motifs.	2001-08-31	11431472
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.	2001-08-28	11431100
Ion conductors derived from cholic acid and spermine: importance of facial hydrophilicity on NA(+) transport and membrane selectivity.	2001-08-08	11480993
On-line identification of trans- and cis-resveratrol by nonaqueous capillary electrophoresis/fluorescence spectroscopy at 77 K.	2001-08	11519961
A double antibody sandwich enzyme-linked immunosorbent assay for the detection of Salmonella using biotinylated monoclonal antibodies.	2001-08	11510654
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.	2001-08	11477651
Non-obese diabetic (NOD) mice exhibit an increased cellular immune response to glycated-LDL but are resistant to high fat diet induced atherosclerosis.	2001-08	11472727
Analysis of post-harvest fungicides by micellar electrokinetic chromatography.	2001-07-27	11521888
Transmembrane ion channels constructed of cholic acid derivatives.	2001-07-27	11463261
Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles.	2001-07-20	11510546
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.	2001-07-15	11476216
Monitored selection of DNA-hybrids forming duplexes with capped terminal C:G base pairs.	2001-07-10	11442395
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.	2001-07	11518324
Stacking and separation of coproporphyrin isomers by acetonitrile-salt mixtures in micellar electrokinetic chromatography.	2001-07	11504047
Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants.	2001-07	11474144
Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.	2001-07	11438506
Synthesis and properties of bile acid phosphoramidites 5'-tethered to antisense oligodeoxynucleotides against HCV.	2001-07	11425584
[Dietary cholesterol modifies pyroglutamyl aminopeptidase activity in mouse frontal cortex. Sexual differences].	2001-06-26	11424043
Surfactant, but not the size of solid lipid nanoparticles (SLN) influences viability and cytokine production of macrophages.	2001-06-19	11397567
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.	2001-06	11414298
Controlled expansion of a molecular cavity in a steroid host compound.	2001-05-16	11457222
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.	2001-05	11605772
Characterization, stability and in-vivo distribution of asialofetuin glycopeptide incorporating DSPC/CHOL liposomes prepared by mild cholate incubation.	2001-04	11697109
Cross-Linking study of cytochrome P450 1A2 in proteoliposomes.	2001-02	11508695
Differential modulation of cellular death and survival pathways by conjugated bile acids.	2001	11707155
Influence of plasma triglyceride and plasma cholesterol levels on the clearance rate of fibrinogen.	2001	11460525

Patents

Sample Use Guides

In Vivo Use Guide

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

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 by `admin` on `Mon Mar 31 17:47:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:16 GMT 2025`
Record UNII	G1JO7801AE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHOLIC ACID

Official Name

English

CHOLBAM

Preferred Name

English

3?,7?,12?-Trihydroxy-5?-cholan-24-oic acid

Systematic Name

English

3,7,12-TRIHYDROXYCHOLANIC ACID

Systematic Name

English

CHOLALIC ACID

Common Name

English

CHOLIC ACID [FCC]

Common Name

English

CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, (3-.ALPHA.,5-.BETA.,7-.ALPHA.,12-.ALPHA.)-

Common Name

English

CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, (3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-

Common Name

English

Cholic acid [WHO-DD]

Common Name

English

URSODEOXYCHOLIC ACID IMPURITY B [EP IMPURITY]

Common Name

English

ORPHACOL

Brand Name

English

CHOLIC ACID [USP-RS]

Common Name

English

CHOLIC ACID [ORANGE BOOK]

Common Name

English

CHOLIC ACID [MI]

Common Name

English

NSC-6135

Code

English

CHOLIC ACID [HSDB]

Common Name

English

CHOLIC ACID [EP IMPURITY]

Common Name

English

CHOLIC ACID [EMA EPAR]

Common Name

English

CHOLIC ACID [USAN]

Common Name

English

CHOLIC ACID [JAN]

Common Name

English

KOLBAM

Brand Name

English

Classification Tree Code System Code

WHO-ATC

A05AA03