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=CC=CC=C1NC2=C3C=CC(Cl)=CC3=NC=C2

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 Glafenine was withdrawn due to the risk of anaphylaxis and acute kidney failure.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Spasm 18 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5421810	Primary		Withdrawn	Unknown Approved Use Unknown
Pain 619 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4141989	Secondary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014-01	24085192
Correction of the Delta phe508 cystic fibrosis transmembrane conductance regulator trafficking defect by the bioavailable compound glafenine.	2010-06	20200141
Identification of inhibitors of ABCG2 by a bioluminescence imaging-based high-throughput assay.	2009-07-15	19567678
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009-06-25	19557182
High-performance liquid chromatographic determination of proquazone and its m-hydroxy metabolite in spiked human plasma and urine.	2007-09-01	17760334
Synthesis of novel 4-substituted-7-trifluoromethylquinoline derivatives with nitric oxide releasing properties and their evaluation as analgesic and anti-inflammatory agents.	2005-10-15	16002298
LC-MS/MS systematic toxicological analysis: comparison of MS/MS spectra obtained with different instruments and settings.	2005-04	15766737
Cytokine release does not improve the sensitivity and specificity of the direct popliteal lymph node assay.	2004-08-05	15212820
Determination of thiocolchicoside in its binary mixtures (thiocolchicoside-glafenine and thiocolchicoside-floctafenine) by TLC-densitometry.	2003-06	12767387
A general unknown screening procedure for drugs and toxic compounds in serum using liquid chromatography-electrospray-single quadrupole mass spectrometry.	2003-02-18	12587676
Impact of glafenine hydrochloride on human endothelial cells and human vascular smooth muscle cells: a substance reducing proliferation, migration and extracellular matrix synthesis.	2003	14642530
Influence of agents affecting voltage-dependent calcium channels and dantrolene on the anticonvulsant action of the AMPA/kainate receptor antagonist LY 300164 in mice.	2002-08	12126870
Ion suppression effects in liquid chromatography-electrospray-ionisation transport-region collision induced dissociation mass spectrometry with different serum extraction methods for systematic toxicological analysis with mass spectra libraries.	2002-06-15	12015269
Investigating the TNP-OVA and direct popliteal lymph node assays for the detection of immunostimulation by drugs associated with anaphylaxis in humans.	2002-05-17	12015798
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001-11	11792017
Synthesis and pharmacological evaluation of analgesic 6-substituted 2(3H)-benzothiazolones.	2001	11765136
Recurrence of biliary drug lithiasis due to dipyridamole.	1997-06	9270928
Immunogenicity of amodiaquine in the rat.	1990	2210868
[13 cases of drug-induced calculi].	1988	2903714
[Identification of a metabolite of floctafenine in urinary calculi].	1987	2892454
Analgesic and non-steroidal anti-inflammatory drug-associated acute renal failure: a prospective collaborative study.	1986-06	2873910
[Occurrence of drug reactions].	1986	2872904
[Detection and diagnosis of drug induced lithiasis].	1983	6139048
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.	1979-05	458805

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 `Mon Mar 31 18:01:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:31 GMT 2025`
Record UNII	46HL4I09AH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLAFENINE

Official Name

English

NSC-757808

Preferred Name

English

GLAFENINE [MART.]

Common Name

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