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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
Enhanced efficiency of the placental barrier to cisplatin through binding to glycocholic acid.
2001 Jul-Aug
Ocular tolerance of absorption enhancers in ophthalmic preparations.
2002
Carriers involved in targeting the cytostatic bile acid-cisplatin derivatives cis-diammine-chloro-cholylglycinate-platinum(II) and cis-diammine-bisursodeoxycholate-platinum(II) toward liver cells.
2002 Apr
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
Examination of the solubilization of drugs by bile salt micelles.
2002 Aug
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.
2002 Dec
Positively charged nanoparticles for improving the oral bioavailability of cyclosporin-A.
2002 Dec 5
[Observation on effect of danxiaoling in supplementary treatment of intrahepatic cholestasis in pregnancy].
2002 Feb
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.
2002 Jul 8
Drug metabolic activity of cultured hepatocytes can synchronize with bile acid concentration in the medium.
2002 Mar
Colesevelam hydrochloride.
2002 May 15
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].
2002 Nov
The human bile salt export pump: characterization of substrate specificity and identification of inhibitors.
2002 Nov
Ion conductors derived from biogenic amines, bile acids, and amino acids.
2002 Nov-Dec
[Maternal-fetal mixed lymphocyte culture in 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
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].
2003
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.
2003 Aug
Substitution of Trp1242 of TM17 alters substrate specificity of human multidrug resistance protein 3.
2003 Feb
Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures.
2003 Feb 1
Sodium glycocholate transport across Caco-2 cell monolayers, and the enhancement of mannitol transport relative to transepithelial electrical resistance.
2003 Feb 18
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.
2003 Feb 4
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
2003 Jan 1
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.
2003 Jul
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.
2003 Mar
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
2003 Nov
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].
2004 Apr
Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin.
2004 Apr
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids.
2004 Aug 6
[Effects of protease inhibitors on intestinal absorption of insulin].
2004 Feb
Transcriptional regulation of human mucin MUC4 by bile acids in oesophageal cancer cells is promoter-dependent and involves activation of the phosphatidylinositol 3-kinase signalling pathway.
2004 Feb 1
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats.
2004 Jan
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.
2004 Jan-Feb
Acid and bile salts induce DNA damage in human oesophageal cell lines.
2004 Jul
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.
2004 Jul 1
Quantification of bile acids directly from plasma by MALDI-TOF-MS.
2004 Mar
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers.
2004 May
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
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules.
2005 Apr 11
[Cholyl glycine (CG)].
2005 Aug
Ileal bile acid-binding protein, functionally associated with the farnesoid X receptor or the ileal bile acid transporter, regulates bile acid activity in the small intestine.
2005 Dec 23
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.
2005 Feb
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).
2005 Feb
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system.
2005 Mar 23
Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism.
2005 Oct
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.
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