GLAFENINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H17ClN2O4
Molecular Weight	372.802
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC(O)COC(=O)C1=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=CC=C1

InChI

InChIKey=GWOFUCIGLDBNKM-UHFFFAOYSA-N

InChI=1S/C19H17ClN2O4/c20-12-5-6-14-17(7-8-21-18(14)9-12)22-16-4-2-1-3-15(16)19(25)26-11-13(24)10-23/h1-9,13,23-24H,10-11H2,(H,21,22)

HIDE SMILES / InChI

Molecular Formula	C19H17ClN2O4
Molecular Weight	372.802
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1675606
Curator's Comment: description was created based on several sources, including http://www.thepharmaletter.com/article/glafenine-french-temp-withdrawal

Glafenine is a non-steroidal anti-inflammatory drug (NSAID). Glafenine was withdrawn due to the risk of anaphylaxis and acute kidney failure.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spasm 18 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5421810	Primary		Withdrawn	Unknown Approved Use Unknown
Pain 614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4141989	Secondary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Occurrence of drug reactions].	1986	2872904
Analgesic and non-steroidal anti-inflammatory drug-associated acute renal failure: a prospective collaborative study.	1986 Jun	2873910
[Identification of a metabolite of floctafenine in urinary calculi].	1987	2892454
Immunogenicity of amodiaquine in the rat.	1990	2210868
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Determination of thiocolchicoside in its binary mixtures (thiocolchicoside-glafenine and thiocolchicoside-floctafenine) by TLC-densitometry.	2003 Jun	12767387
LC-MS/MS systematic toxicological analysis: comparison of MS/MS spectra obtained with different instruments and settings.	2005 Apr	15766737
High-performance liquid chromatographic determination of proquazone and its m-hydroxy metabolite in spiked human plasma and urine.	2007 Jul-Aug	17760334
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009 Jun 25	19557182
Correction of the Delta phe508 cystic fibrosis transmembrane conductance regulator trafficking defect by the bioavailable compound glafenine.	2010 Jun	20200141

Patents

Sample Use Guides

In Vivo Use Guide

200-400 mg, 3-4 times per day

Route of Administration: Oral

In Vitro Use Guide

human aortic smooth muscle cells (haSMCs) and human endothelial cells (ECs) were seeded in tissue culture flasks. The cells were treated for 4 days with glafenine hydrochloride (10 uM, 50 uM, 100 uM). Half of the treated groups were incubated again with glafenine hydrochloride, the other half received medium free of glafenine hydrochloride every 4 days until day 20.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:17 UTC 2023` Edited by `admin` on `Fri Dec 15 15:34:17 UTC 2023`
Record UNII	46HL4I09AH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLAFENINE

Official Name

English

GLAFENINE [MART.]

Common Name

English

NSC-757808

Code

English

GLAPHENINE

Common Name

English

R-1707

Code

English

GLAFENINE [JAN]

Common Name

English

Glafenine [WHO-DD]

Common Name

English

glafenine [INN]

Common Name

English

R 1707

Code

English

GLYCERYLAMINOPHENAQUINE

Common Name

English

GLAFENINE [MI]

Common Name

English

2,3-DIHYDROXYPROPYL N-(7-CHLORO-4-QUINOLYL) ANTHRANILATE

Common Name

English

GLAFENIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241