SODIUM GLYCOCHOLATE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28942640

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

Condition	Modality	Targets	Highest Phase	Product
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061917	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The lung as a route for systemic delivery of therapeutic proteins and peptides.	2001	11686885
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	11305600
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.	2001 Apr 17	11292547
Study of partition of nitrazepam in bile salt micelles and the role of lecithin.	2001 Feb	11272316
Penetration of verapamil hydrochloride in the presence of sodium glycocholate as penetration enhancer through mucous membrane.	2001 Jan	11210675
Enhanced efficiency of the placental barrier to cisplatin through binding to glycocholic acid.	2001 Jul-Aug	11724343
Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones.	2001 Oct	11680582
Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport.	2001 Oct 1	11585759
Absorption of water-soluble compounds with different molecular weights and.	2001 Oct 19	11578749
Bile salt aggregates in the gas phase: an electrospray ionization mass spectrometric study.	2002 Apr 15	12007103
Solubilization of drugs by physiological mixtures of bile salts.	2002 Aug	12240947
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.	2002 Jan	11728521
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.	2002 Jul 8	12086728
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].	2002 Nov	12487922
[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy].	2002 Sep	12411010
[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy].	2002 Sep	12411009
A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test.	2002 Sep	12231118
Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH.	2003 Apr 1	12659967
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.	2003 Aug	12883481
Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection.	2003 Aug 8	12899981
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.	2003 Jul	12820155
Differential effects of metformin on bile salt absorption from the jejunum and ileum.	2003 Mar	12630937
Feedback regulation of bile acid synthesis in primary human hepatocytes: evidence that CDCA is the strongest inhibitor.	2003 Oct	14512880
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].	2004 Apr	15143715
Functional assessment of bacterial colonization in patients with ileal pouch-anal anastomosis and Brooke ileostomy.	2004 Aug	15484354
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.	2004 Jan-Feb	14715004
[Study on relationship between serum cholylglycine and placental apoptosis in patients with intrahepatic cholestasis of pregnancy].	2004 Jul	15347465
Quantification of bile acids directly from plasma by MALDI-TOF-MS.	2004 Mar	14747894
Noninvasive methods to determine the critical micelle concentration of some bile acid salts.	2004 Nov 1	15464960
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s.	2004 Oct 1	15387580
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11.	2005 Apr	15791618
[Cholyl glycine (CG)].	2005 Aug	16149646
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).	2005 Feb	15537867
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles.	2005 Oct 3	16023752
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.	2005 Sep-Oct	16145315
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.	2005 Sep-Oct	16101123

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

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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