SODIUM CHOLATE

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

Structure Search

SMILES

[Na+].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=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

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H39O5
Molecular Weight	407.5635
Charge	-1
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
Differential modulation of cellular death and survival pathways by conjugated bile acids.	2001	11707155
Separation of neutral compounds by microemulsion electrokinetic chromatography: fundamental studies on selectivity.	2001 Apr	11379955
On-line identification of trans- and cis-resveratrol by nonaqueous capillary electrophoresis/fluorescence spectroscopy at 77 K.	2001 Aug	11519961
A double antibody sandwich enzyme-linked immunosorbent assay for the detection of Salmonella using biotinylated monoclonal antibodies.	2001 Aug	11510654
Ion conductors derived from cholic acid and spermine: importance of facial hydrophilicity on NA(+) transport and membrane selectivity.	2001 Aug 8	11480993
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.	2001 Dec	11709519
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.	2001 Dec	11709518
Cross-Linking study of cytochrome P450 1A2 in proteoliposomes.	2001 Feb	11508695
Determination of alkylphenol ethoxylates by micellar electrokinetic chromatography with bile salts.	2001 Feb	11258765
Comparative topical pheromonotropic activity of insect pyrokinin/PBAN amphiphilic analogs incorporating different fatty and/or cholic acid components.	2001 Feb	11179822
Paradoxical increase in nitric oxide synthase activity in hypercholesterolaemic rats with impaired renal function and decreased activity of nitric oxide.	2001 Feb	11158398
Anodic electrochemical oxidation of cholic acid.	2001 Feb	11146084
Enzymatic syntheses of T antigen-containing glycolipid mimicry using the transglycosylation activity of endo-alpha-N-acetylgalactosaminidase.	2001 Feb 28	11269400
[Effect of selenium on serum, hepatic and lipoprotein lipids concentration in rats fed on a high-cholesterol diet].	2001 Jan	11201167
Determination of synthesized alpha-vitamin E by micellar electrokinetic chromatography.	2001 Jan	11197165
Enzymatic synthesis of aliphatic beta-lactosides as mimic units of glycosphingolipids by use of Trichoderma reesei cellulase.	2001 Jan 1	11361028
Importance of packing coefficients of host cavities in the isomerization of open host frameworks: guest-size-dependent isomerization in cholic acid inclusion crystals with monosubstituted benzenes.	2001 Jan 5	11205013
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	11518324
Stacking and separation of coproporphyrin isomers by acetonitrile-salt mixtures in micellar electrokinetic chromatography.	2001 Jul	11504047
Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles.	2001 Jul 20	11510546
Analysis of post-harvest fungicides by micellar electrokinetic chromatography.	2001 Jul 27	11521888
Transcriptional regulation of the human sterol 27-hydroxylase gene (CYP27) and promoter mapping.	2001 Jun	11395030
Development and validation of a cholate binding capacity method for DMP 504, a bile acid sequestrant.	2001 Jun	11377012
Expression of sterol 12alpha-hydroxylase alters bile acid pool composition in primary rat hepatocytes and in vivo.	2001 Jun	11375960
Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradation.	2001 Jun	11375905
Molecular umbrella-assisted transport of glutathione across a phospholipid membrane.	2001 Jun 13	11389618
[3-oxo-delta 4-steroid 5 beta-reductase deficiency].	2001 Mar	11347080
Ursodeoxycholic acid administration in patients with cholestasis of pregnancy: effects on primary bile acids in babies and mothers.	2001 Mar	11230728
Transcriptional regulation of the human sterol 12alpha-hydroxylase gene (CYP8B1): roles of heaptocyte nuclear factor 4alpha in mediating bile acid repression.	2001 Nov 9	11535594
Colonic transit influences deoxycholic acid kinetics.	2001 Oct	11606495
Farnesoid X-activated receptor induces apolipoprotein C-II transcription: a molecular mechanism linking plasma triglyceride levels to bile acids.	2001 Oct	11579204
Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450.	2001 Oct 19	11509573
Simultaneous detection of cholyl adenylate and coenzyme A thioester utilizing liquid chromatography/electrospray ionization mass spectrometry.	2001 Sep	11708055
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.	2001 Sep	11699836
Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol).	2001 Sep 11	11532566
The association of manganese superoxide dismutase expression in Barrett's esophageal progression with MnTBAP and curcumin oil therapy.	2012 Aug	22316666

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 17:49:48 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:48 GMT 2025`
Record UNII	NU3Y4CCH8Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM CHOLATE

Official Name

English

CHOLATE SODIUM

Preferred Name

English

Cholate sodium [WHO-DD]

Common Name

English

CHOLIC ACID, SODIUM SALT

Common Name

English

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

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID9033979