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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H42NO6.Na
Molecular Weight 487.6045
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM GLYCOCHOLATE

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)NCC([O-])=O

InChI

InChIKey=OABYVIYXWMZFFJ-ZUHYDKSRSA-M
InChI=1S/C26H43NO6.Na/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29;/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33);/q;+1/p-1/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C26H42NO6
Molecular Weight 464.6148
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

Glycocholic acid (GCA) is an important metabolite of bile acids, a conjugate of cholic acid with glycine. GCA urine levels are expected to be a specific diagnostic biomarker for hepatocellular carcinoma (HCC). The average GCA concentrations of HCC patients in plasma and urine were about 25 and 2.8 times than that of healthy volunteers.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The lung as a route for systemic delivery of therapeutic proteins and peptides.
2001
Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Study of partition of nitrazepam in bile salt micelles and the role of lecithin.
2001 Feb
Penetration of verapamil hydrochloride in the presence of sodium glycocholate as penetration enhancer through mucous membrane.
2001 Jan
Enhanced efficiency of the placental barrier to cisplatin through binding to glycocholic acid.
2001 Jul-Aug
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.
2001 Oct
Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport.
2001 Oct 1
Absorption of water-soluble compounds with different molecular weights and.
2001 Oct 19
Bile salt aggregates in the gas phase: an electrospray ionization mass spectrometric study.
2002 Apr 15
Solubilization of drugs by physiological mixtures of bile salts.
2002 Aug
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.
2002 Jan
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.
2002 Jul 8
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].
2002 Nov
[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy].
2002 Sep
[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy].
2002 Sep
A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test.
2002 Sep
Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH.
2003 Apr 1
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.
2003 Aug
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.
2003 Aug 8
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.
2003 Jul
Differential effects of metformin on bile salt absorption from the jejunum and ileum.
2003 Mar
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.
2003 Oct
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].
2004 Apr
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy.
2004 Aug
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.
2004 Jan-Feb
[Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy].
2004 Jul
Quantification of bile acids directly from plasma by MALDI-TOF-MS.
2004 Mar
Noninvasive methods to determine the critical micelle concentration of some bile acid salts.
2004 Nov 1
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.
2004 Oct 1
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11.
2005 Apr
[Cholyl glycine (CG)].
2005 Aug
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).
2005 Feb
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles.
2005 Oct 3
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.
2005 Sep-Oct
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:17 GMT 2023
Record UNII
V06CXA1W3K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM GLYCOCHOLATE
Common Name English
SODIUM CHOLYLGLYCINATE
Common Name English
SODIUM GLYCYLCHOLATE
Common Name English
MONOSODIUM GLYCOCHOLATE
Common Name English
N-CHOLYLGLYCINE SODIUM SALT
Common Name English
NSC-35609
Code English
GLYCOCHOLIC ACID, SODIUM SALT
Common Name English
GLYCINE, N-((3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)-3,7,12-TRIHYDROXY-24-OXOCHOLAN-24-YL)-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
CHEBI
36273
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
CAS
863-57-0
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
SMS_ID
100000172105
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
NSC
35609
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
PUBCHEM
23670522
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-730-9
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
FDA UNII
V06CXA1W3K
Created by admin on Fri Dec 15 15:10:17 GMT 2023 , Edited by admin on Fri Dec 15 15:10:17 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE