Glafenine - CAS 3820-67-5
Catalog number: 3820-67-5
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H17ClN2O4
Molecular Weight:
372.80
COA:
Inquire
Targets:
Others
Description:
Glafenine is a non-steroidal analgesic agent, shows significant antiinflammatory activity.
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Purity:
≥98%
Appearance:
Solid powder
Synonyms:
2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate; 1-Glyceryl N-(7-chloro-4-quinolyl)anthranilate
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Wdely used for the treatment of pains of various origins.
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
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)
Canonical SMILES:
C1=CC=C(C(=C1)C(=O)OCC(CO)O)NC2=C3C=CC(=CC3=NC=C2)Cl
1.Bioactivation of glafenine by human liver microsomes and peroxidases: identification of electrophilic iminoquinone species and GSH conjugates.
Wen B1, Moore DJ. Drug Metab Dispos. 2011 Sep;39(9):1511-21. doi: 10.1124/dmd.111.039396. Epub 2011 May 31.
Glafenine (Privadol; 2,3-dihydroxypropyl 2-[(7-chloro-4-quinolinyl) amino]benzoate) is a non-narcotic analgesic agent widely used for the treatment of pains of various origins. Severe liver toxicity and a high incidence of anaphylaxis were reported in patients treated with glafenine, eventually leading to its withdrawal from the market in most countries. It is proposed that bioactivation of glafenine and subsequent binding of reactive metabolite(s) to critical cellular proteins play a causative role. The study described herein aimed at characterizing pathways of glafenine bioactivation and the metabolic enzymes involved. Two GSH conjugates of glafenine were detected in human liver microsomal incubations using liquid chromatography tandem mass spectrometry. The structures of detected conjugates were determined as GSH adducts of 5-hydroxyglafenine (M3) and 5-hydroxy glafenic acid (M4), respectively. GSH conjugation took place with a strong preference at C6 of the benzene ring of glafenine, ortho to the carbonyl moiety.
2.Simultaneous HPLC determination of thiocolchicoside and glafenine as well as thiocolchicoside and floctafenine in their combined dosage forms.
Walash M1, Belal F, Eid M, el-Abass SA. J Chromatogr Sci. 2011 Feb;49(2):159-64.
Sensitive and accurate high-performance liquid chromatographic methods have been developed for the simultaneous determination of thiocolchicoside (TC)-glafenine (GF) (Mix I) and thiocolchicoside-floctafenine (FN) (Mix II) in their pharmaceutical formulations. The analysis for both mixtures was performed using 250 mm × 4.6 mm i.d., 5 μm particle size C18 Waters Symmetry column. The mobile phase consisted of methanol-0.035 M phosphate buffer (50:50, v/v) of pH 4.5 for Mix I and methanol-0.03 M phosphate buffer (70:30, v/v) of pH 4 for Mix II with flow rate of 1 mL/min and UV detection at 400 nm in both cases. The calibration plots were rectilinear over the concentration range of 0.2-2 μg/mL for TC in both mixtures and 20-200 μg/mL for each of GF and FN . The limits of detection for TC and GF were 0.05 μg/mL and 0.62 μg/mL, respectively, and for TC and FN were 0.02 μg/mL and 0.70 μg/mL, respectively. Additionally, the proposed methods were successfully applied to their combined tablets with average percentage recoveries of 100.
3.Glafenine-induced intestinal injury in zebrafish is ameliorated by μ-opioid signaling via enhancement of Atf6-dependent cellular stress responses.
Goldsmith JR1, Cocchiaro JL, Rawls JF, Jobin C. Dis Model Mech. 2013 Jan;6(1):146-59. doi: 10.1242/dmm.009852. Epub 2012 Aug 23.
Beside their analgesic properties, opiates exert beneficial effects on the intestinal wound healing response. In this study, we investigated the role of μ-opioid receptor (MOR) signaling on the unfolded protein response (UPR) using a novel zebrafish model of NSAID-induced intestinal injury. The NSAID glafenine was administered to zebrafish larvae at 5 days post-fertilization (dpf) for up to 24 hours in the presence or absence of the MOR-specific agonist DALDA. By analysis with histology, transmission electron microscopy and vital dye staining, glafenine-treated zebrafish showed evidence of endoplasmic reticulum and mitochondrial stress, with disrupted intestinal architecture and halted cell stress responses, alongside accumulation of apoptotic intestinal epithelial cells in the lumen. Although the early UPR marker BiP was induced with glafenine-induced injury, downstream atf6 and s-xbp1 expression were paradoxically not increased, explaining the halted cell stress responses.
4.Application of H-point standard additions method to spectrophotometric and spectrofluorimetric determinations of glafenine and glafenic acid in mixtures.
Sabry SM1, Khamis EF. Talanta. 2000 May 5;51(6):1219-31.
H-point standard additions method (HPSAM), based on spectrophotometric and spectrofluorimetric measurements, was proposed for simultaneous determination of glafenine (G) and glafenic acid (GA). A study of the absorption spectra of G and GA in various pH media has been carried out. Reasonably resolved UV-absorption spectra were obtained with a solution adjusted at pH 4.5 with citric acid-phosphate buffer. Additionally, the fluorescence properties in aqueous micellar systems of anionic, cationic and non-ionic surfactants were investigated. Well resolved fluorescence spectra were established in aqueous Triton X-100 solution at pH 7.8 (citric acid-phosphate buffer). As a comparative method, UV-derivative spectrophotometry (based on zero-crossing technique) was suggested. First-derivative value at 352 nm ((1)D(352)) and second-derivative value at 366 nm ((2)D(366)) were selected for the quantification of G and GA, respectively. The relative standard deviations of the proposed methods approximate 2%.
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Chemical Structure

CAS 3820-67-5 Glafenine

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