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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
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
Penetration of verapamil hydrochloride in the presence of sodium glycocholate as penetration enhancer through mucous membrane.
2001 Jan
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
Nasal absorption enhancement strategies for therapeutic peptides: an in vitro study using cultured human nasal epithelium.
2002 Apr 26
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
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
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].
2002 Nov
Functional expression of the canalicular bile salt export pump of human liver.
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
[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
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
Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).
2003 Feb
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
Variation in plasma amino acid concentrations during a cycling competition.
2003 Jun
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.
2003 Mar
Protease inhibitors: synthesis of bacterial collagenase and matrix metalloproteinase inhibitors incorporating arylsulfonylureido and 5-dibenzo-suberenyl/suberyl moieties.
2003 May 15
Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats.
2003 Nov
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.
2003 Nov
Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium.
2004 Apr
[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
[Effects of protease inhibitors on intestinal absorption of insulin].
2004 Feb
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
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers.
2004 May
Noninvasive methods to determine the critical micelle concentration of some bile acid salts.
2004 Nov 1
Evaluation of different toxicity assays applied to proliferating cells and to stratified epithelium in relation to permeability enhancement with glycocholate.
2004 Oct
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.
2004 Oct 1
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules.
2005 Apr 11
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
Quantitative estimation of the effects of bile salt surfactant systems on insulin stability and permeability in the rat intestine using a mass balance model.
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
Octreotide induced prolongation of colonic transit increases faecal anaerobic bacteria, bile acid metabolising enzymes, and serum deoxycholic acid in patients with acromegaly.
2005 May
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man.
2005 Oct
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins.
2005 Oct 28
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles.
2005 Oct 3
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 Wed Jul 05 22:41:58 UTC 2023
Edited
by admin
on Wed Jul 05 22:41:58 UTC 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 Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
CAS
863-57-0
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
SMS_ID
100000172105
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
NSC
35609
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
PUBCHEM
23670522
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-730-9
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
FDA UNII
V06CXA1W3K
Created by admin on Wed Jul 05 22:41:58 UTC 2023 , Edited by admin on Wed Jul 05 22:41:58 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE