U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H39O5.Na
Molecular Weight 430.5541
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM CHOLATE

SMILES

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

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 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H39O5
Molecular Weight 407.5644
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.42646405E12
Primary
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

1.42646405E12
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
PubMed

PubMed

TitleDatePubMed
Role of phospholipids in reconstituted cytochrome P450 3A form and mechanism of their activation of catalytic activity.
1992 Jul 7
Cloning and sequencing of a novel murine liver carboxylesterase cDNA.
1998 Apr 29
Differential modulation of cellular death and survival pathways by conjugated bile acids.
2001
Influence of plasma triglyceride and plasma cholesterol levels on the clearance rate of fibrinogen.
2001
Characterization, stability and in-vivo distribution of asialofetuin glycopeptide incorporating DSPC/CHOL liposomes prepared by mild cholate incubation.
2001 Apr
Design and properties of hepatitis C virus antisense oligonucleotides for liver specific drug targeting.
2001 Apr-Jul
On-line identification of trans- and cis-resveratrol by nonaqueous capillary electrophoresis/fluorescence spectroscopy at 77 K.
2001 Aug
A double antibody sandwich enzyme-linked immunosorbent assay for the detection of Salmonella using biotinylated monoclonal antibodies.
2001 Aug
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
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
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
Cross-Linking study of cytochrome P450 1A2 in proteoliposomes.
2001 Feb
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
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
Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes.
2001 Jul 15
Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles.
2001 Jul 20
Analysis of post-harvest fungicides by micellar electrokinetic chromatography.
2001 Jul 27
Transmembrane ion channels constructed of cholic acid derivatives.
2001 Jul 27
Monitored selection of DNA-hybrids forming duplexes with capped terminal C:G base pairs.
2001 Jul-Aug
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
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
Transcriptional regulation of the human sterol 12alpha-hydroxylase gene (CYP8B1): roles of heaptocyte nuclear factor 4alpha in mediating bile acid repression.
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
Evidence for an umbrella mechanism of bilayer transport.
2001 Oct 10
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
Potency of select statin drugs in a new mouse model of hyperlipidemia and atherosclerosis.
2001 Oct 23
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
The association of manganese superoxide dismutase expression in Barrett's esophageal progression with MnTBAP and curcumin oil therapy.
2012 Aug
Eicosapentaenoic acid attenuates hepatic accumulation of cholesterol esters but aggravates liver injury and inflammation in mice fed a cholate-supplemented high-fat diet.
2013
An Atherogenic Paigen-Diet Aggravates Nephropathy in Type 2 Diabetic OLETF Rats.
2015
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
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 Sat Jun 26 07:10:37 UTC 2021
Edited
by admin
on Sat Jun 26 07:10:37 UTC 2021
Record UNII
NU3Y4CCH8Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM CHOLATE
INCI  
INCI  
Official Name English
CHOLATE SODIUM
WHO-DD  
Common Name English
CHOLATE SODIUM [WHO-DD]
Common Name English
CHOLIC ACID, SODIUM SALT
Common Name English
SODIUM CHOLATE [INCI]
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
361-09-1
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
EVMPD
SUB13343MIG
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-643-5
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
RXCUI
2286239
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
FDA UNII
NU3Y4CCH8Z
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
MESH
D020358
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
CAS
361-09-1
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
PUBCHEM
23668194
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
WIKIPEDIA
Sodium cholate
Created by admin on Sat Jun 26 07:10:37 UTC 2021 , Edited by admin on Sat Jun 26 07:10:37 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
PARENT -> SALT/SOLVATE
TRANSPORTER -> INHIBITOR
LABELED -> NON-LABELED