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
Enhanced efficiency of the placental barrier to cisplatin through binding to glycocholic acid.	2001 Jul-Aug	11724343
Ocular tolerance of absorption enhancers in ophthalmic preparations.	2002	12049486
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	11901224
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
Examination of the solubilization of drugs by bile salt micelles.	2002 Aug	12115803
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.	2002 Dec	12456554
Positively charged nanoparticles for improving the oral bioavailability of cyclosporin-A.	2002 Dec 5	12433438
[Observation on effect of danxiaoling in supplementary treatment of intrahepatic cholestasis in pregnancy].	2002 Feb	12585148
Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state.	2002 Jul 8	12086728
Drug metabolic activity of cultured hepatocytes can synchronize with bile acid concentration in the medium.	2002 Mar	11835266
Colesevelam hydrochloride.	2002 May 15	12040732
[Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy].	2002 Nov	12487922
The human bile salt export pump: characterization of substrate specificity and identification of inhibitors.	2002 Nov	12404239
Ion conductors derived from biogenic amines, bile acids, and amino acids.	2002 Nov-Dec	12440868
[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy].	2002 Sep	12411010
A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test.	2002 Sep	12231118
[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis].	2003	14653242
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane.	2003 Aug	12883481
Substitution of Trp1242 of TM17 alters substrate specificity of human multidrug resistance protein 3.	2003 Feb	12388190
Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures.	2003 Feb 1	12486725
Sodium glycocholate transport across Caco-2 cell monolayers, and the enhancement of mannitol transport relative to transepithelial electrical resistance.	2003 Feb 18	12550793
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.	2003 Feb 4	12569201
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.	2003 Jan 1	12220224
Influence of emulsifiers on the crystallization of solid lipid nanoparticles.	2003 Jul	12820155
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.	2003 Mar	12601352
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.	2003 Nov	12842829
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy].	2004 Apr	15143715
Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin.	2004 Apr	14999743
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids.	2004 Aug 6	15281152
[Effects of protease inhibitors on intestinal absorption of insulin].	2004 Feb	15127624
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	14583090
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats.	2004 Jan	14980001
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction.	2004 Jan-Feb	14715004
Acid and bile salts induce DNA damage in human oesophageal cell lines.	2004 Jul	15215332
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.	2004 Jul 1	15214790
Quantification of bile acids directly from plasma by MALDI-TOF-MS.	2004 Mar	14747894
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers.	2004 May	15069095
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
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules.	2005 Apr 11	15778050
[Cholyl glycine (CG)].	2005 Aug	16149646
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	16230354
Micellar electrokinetic chromatography of bilirubin, related compounds, and selected drugs with mixtures of binary bile salts.	2005 Feb	15714544
Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).	2005 Feb	15537867
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.	2005 Jan	15297262
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system.	2005 Mar 23	15725562
Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism.	2005 Oct	15985617
Effect of tibolone on turnover of cholesterol to bile acids in ovariectomized rats.	2005 Sep-Oct	16145315

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