Glafenine

Title: Glafenine
CAS Registry Number: 3820-67-5
CAS Name: 2-[(7-Chloro-4-quinolinyl)amino]benzoic acid 2,3-dihydroxypropyl ester
Additional Names: N-(7-chloro-4-quinolyl)anthranilic acid 2,3-dihydroxypropyl ester; 4-[(2-carboxyphenyl)amino]-7-chloroquinoline a-monoglyceride; 2-[(7-chloro-4-quinolyl)amino]benzoic acid a-glyceride; 2,3-dihydroxypropyl N-(7-chloro-4-quinolyl)anthranilate; glycerylaminophenaquine; glaphenine
Manufacturers' Codes: R-1707
Trademarks: Privadol (Sanofi-Synthelabo)
Molecular Formula: C19H17ClN2O4
Molecular Weight: 372.80
Percent Composition: C 61.21%, H 4.60%, Cl 9.51%, N 7.51%, O 17.17%
Literature References: Prepn: FR M2413; A. Allais, J. Meier, US 3232944 (1964, 1966 both to Roussel-UCLAF); G. Mouzin et al., Synthesis 1980, 54. HPLC determn in plasma: M.-C. Tournet et al., J. Chromatogr. 224, 348 (1981). Biotransformation in the rat and man: J. Pottier et al., Eur. J. Drug Metab. Pharmacokinet. 4, 109 (1979). Bioavailability, absorption: F. Moolenaar et al., Int. J. Pharm. 4, 195 (1980). Alkalimetric determn: M. S. Tawakkol et al., Pharmazie 36, 163 (1981). Comprehensive description: A. A. Badwan et al., Anal. Profiles Drug Subs. Excip. 21, 197-232 (1992).
Properties: Pale yellow prisms, mp 169-170° (Mouzin); also reported as mp 165° (Allais, Meier). Practically insol in water. Slightly sol in abs alcohol, acetone, ether, benzene, chloroform; sol in dil aq alkalies and acids. Soly at 30°C (g/100 ml): hexane <0.001, water 0.001, chloroform 0.260, acetone 0.297, ethanol 0.700, 0.1N HCl 1.295. pKa (20°C) 7.2. uv max (methanol): 356, 225, 255 nm; (0.1N HCl) 342, 223, 252 nm. LD50 orally in mice: >2 g/kg (Allais, Meier).
Melting point: mp 169-170° (Mouzin); mp 165° (Allais, Meier)
pKa: pKa (20°C) 7.2
Absorption maximum: uv max (methanol): 356, 225, 255 nm; (0.1N HCl) 342, 223, 252 nm
Toxicity data: LD50 orally in mice: >2 g/kg (Allais, Meier)
Therap-Cat: Analgesic.
Keywords: Analgesic (Non-Narcotic).
Status: This monograph has been retired and is no longer subject to revision or update.
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Glafenine
Glafenine.svg
Systematic (IUPAC) name
2,3-Dihydroxypropyl 2-[(7-chloro-4-quinolinyl)amino]benzoate
Clinical data
Legal status  ?
Identifiers
CAS number 3820-67-5
ATC code N02BG03
PubChem CID 3474
ChemSpider 3355
ChEBI CHEBI:31653 YesY
Chemical data
Formula C19H17ClN2O4 
Mol. mass 372.802 g/mol

Glafenine is a non-steroidal anti-inflammatory drug (NSAID). Use of glafenine is limited due to the risk of anaphylaxis and acute renal failure.[1][2]