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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 of SODIUM CHOLATE

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

HIDE SMILES / InChI

Molecular Formula C24H39O5
Molecular Weight 407.5635
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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

2015
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

2015
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
Bile acids: natural ligands for an orphan nuclear receptor.
1999 May 21
Elevated cholesterol metabolism and bile acid synthesis in mice lacking membrane tyrosine kinase receptor FGFR4.
2000 May 19
Bile acid acyl adenylate: a possible intermediate to produce a protein-bound bile acid.
2001
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Design of rolipram-loaded nanoparticles: comparison of two preparation methods.
2001 Apr 28
Bile acid-oligodeoxynucleotide conjugates: synthesis and liver excretion in rats.
2001 Apr 9
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.
2001 Dec
Alterations in intestinal microflora, faecal bile acids and short chain fatty acids in dextran sulphate sodium-induced experimental acute colitis in rats.
2001 Feb
Paradoxical increase in nitric oxide synthase activity in hypercholesterolaemic rats with impaired renal function and decreased activity of nitric oxide.
2001 Feb
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.
2001 Feb 16
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
Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver.
2001 Jul
Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles.
2001 Jul 20
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
Molecular umbrella-assisted transport of glutathione across a phospholipid membrane.
2001 Jun 13
Bilirubin-induced apoptosis in cultured rat neural cells is aggravated by chenodeoxycholic acid but prevented by ursodeoxycholic acid.
2001 Mar
Ursodeoxycholic acid administration in patients with cholestasis of pregnancy: effects on primary bile acids in babies and mothers.
2001 Mar
Structural consequences of metal complexation of cyclo[Pro-Phe-Phe-Ala-Xaa]2 decapeptides.
2001 Mar 16
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
In vitro excystation of Paragonimus heterotremus metacercariae.
2001 Oct
Potency of select statin drugs in a new mouse model of hyperlipidemia and atherosclerosis.
2001 Oct 23
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
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 Fri Dec 15 15:11:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:48 GMT 2023
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
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
EVMPD
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
ECHA (EC/EINECS)
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
RXCUI
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
FDA UNII
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
MESH
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
CAS
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
PUBCHEM
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
CHEBI
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
WIKIPEDIA
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
SMS_ID
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
Related Record Type Details
TRANSPORTER -> INHIBITOR
PARENT -> SALT/SOLVATE
LABELED -> NON-LABELED