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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 of GLAFENINE

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

Description
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 Glafenine was withdrawn due to the risk of anaphylaxis and acute kidney failure.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

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Unknown

Approved Use

Unknown
Secondary
Withdrawn
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
1979 May
[Detection and diagnosis of drug induced lithiasis].
1983
[Occurrence of drug reactions].
1986
Analgesic and non-steroidal anti-inflammatory drug-associated acute renal failure: a prospective collaborative study.
1986 Jun
[Identification of a metabolite of floctafenine in urinary calculi].
1987
[13 cases of drug-induced calculi].
1988
Immunogenicity of amodiaquine in the rat.
1990
Recurrence of biliary drug lithiasis due to dipyridamole.
1997 Jun
Synthesis and pharmacological evaluation of analgesic 6-substituted 2(3H)-benzothiazolones.
2001
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
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 Jun 15
Impact of glafenine hydrochloride on human endothelial cells and human vascular smooth muscle cells: a substance reducing proliferation, migration and extracellular matrix synthesis.
2003
A general unknown screening procedure for drugs and toxic compounds in serum using liquid chromatography-electrospray-single quadrupole mass spectrometry.
2003 Jan-Feb
LC-MS/MS systematic toxicological analysis: comparison of MS/MS spectra obtained with different instruments and settings.
2005 Apr
Synthesis of novel 4-substituted-7-trifluoromethylquinoline derivatives with nitric oxide releasing properties and their evaluation as analgesic and anti-inflammatory agents.
2005 Oct 15
High-performance liquid chromatographic determination of proquazone and its m-hydroxy metabolite in spiked human plasma and urine.
2007 Jul-Aug
Identification of inhibitors of ABCG2 by a bioluminescence imaging-based high-throughput assay.
2009 Jul 15
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.
2009 Jun 25
Correction of the Delta phe508 cystic fibrosis transmembrane conductance regulator trafficking defect by the bioavailable compound glafenine.
2010 Jun
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 Jan
Patents

Patents

US8114892 B2
2

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.
Name Type Language
GLAFENINE
INN   JAN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
WHO-VATC QN02BG03
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
WHO-ATC N02BG03
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
Code System Code Type Description
EVMPD
SUB07909MIG
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
PUBCHEM
3474
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
CAS
3820-67-5
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
MERCK INDEX
m745
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL146095
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
SMS_ID
100000080419
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
MESH
D005897
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
223-315-7
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
INN
1890
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
WIKIPEDIA
Glafenine
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
DRUG CENTRAL
1297
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
NSC
757808
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
NCI_THESAURUS
C72119
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
FDA UNII
46HL4I09AH
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
CHEBI
31653
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID1048546
Created by admin on Fri Dec 15 15:34:17 GMT 2023 , Edited by admin on Fri Dec 15 15:34:17 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of GLAFENINE
SALT/SOLVATE (PARENT)
Structure of GLAFENINE HYDROCHLORIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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