GLAFENINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H17ClN2O4.ClH
Molecular Weight	409.263
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=CEUMONXVSJOJIH-UHFFFAOYSA-N

InChI=1S/C19H17ClN2O4.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 Glafenine was withdrawn due to the risk of anaphylaxis and acute kidney failure.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Spasm 18 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5421810	Primary		Withdrawn	Unknown Approved Use Unknown
Pain 614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4141989	Secondary		Withdrawn	Unknown Approved Use Unknown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
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.	1979 May	458805
[Detection and diagnosis of drug induced lithiasis].	1983	6139048
[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
[13 cases of drug-induced calculi].	1988	2903714
Immunogenicity of amodiaquine in the rat.	1990	2210868
Recurrence of biliary drug lithiasis due to dipyridamole.	1997 Jun	9270928
Synthesis and pharmacological evaluation of analgesic 6-substituted 2(3H)-benzothiazolones.	2001	11765136
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
Cytokine release does not improve the sensitivity and specificity of the direct popliteal lymph node assay.	2004 Aug 5	15212820
High-performance liquid chromatographic determination of proquazone and its m-hydroxy metabolite in spiked human plasma and urine.	2007 Jul-Aug	17760334
Identification of inhibitors of ABCG2 by a bioluminescence imaging-based high-throughput assay.	2009 Jul 15	19567678
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
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	24085192

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 `Sat Dec 16 10:04:12 GMT 2023` Edited by `admin` on `Sat Dec 16 10:04:12 GMT 2023`
Record UNII	MS23T96ZZP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLAFENINE HYDROCHLORIDE

Common Name

English

GLAFENIN HYDROCHLORIDE

Common Name

English

Glafenine hydrochloride [WHO-DD]

Common Name

English

(±)-GLAFENINE HYDROCHLORIDE

Common Name

English

BENZOIC ACID, 2-((7-CHLORO-4-QUINOLINYL)AMINO)-, 2,3-DIHYDROXYPROPYL ESTER, HYDROCHLORIDE (1:1)

Common Name

English

Code System Code Type Description

FDA UNII

MS23T96ZZP