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Merck
CN

Z2625

Zomepirac sodium salt

Synonym(s):

5-(p-Chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid sodium-potassium salt

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About This Item

Linear Formula:
C15H13ClNO3Na
CAS Number:
64092-48-4
Molecular Weight:
313.71
NACRES:
NA.77
PubChem Substance ID:
24902176
UNSPSC Code:
12161501
EC Number:
264-669-2
MDL number:
MFCD00057223

Key Documents

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InChI key

SEEXPXUCHVGZGU-UHFFFAOYSA-M

InChI

1S/C15H14ClNO3.Na/c1-9-7-12(8-13(18)19)17(2)14(9)15(20)10-3-5-11(16)6-4-10;/h3-7H,8H2,1-2H3,(H,18,19);/q;+1/p-1

SMILES string

Cc1cc(CC(=O)O[Na])n(C)c1C(=O)c2ccc(Cl)cc2

Quality Level

200

Application

An NSAID. Circumvents MRP-mediated multidrug resistance. Significantly increases the cytotoxicity of the anthracyclines (doxorubicin, daunorubicin and epirubicin), as well as teniposide, VP-16 and vincristine.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000366823
0000366823
0000274405
0000274405
116H0298

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Mark P Grillo et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(11), 1429-1436 (2003-10-23)
Zomepirac (ZP), a nonsteroidal anti-inflammatory drug that was withdrawn from use, is metabolized to zomepirac-1-O-acyl-glucuronide (ZP-1-O-G), a chemically reactive conjugate that has been implicated in the toxicity of the drug. In the present studies, we investigated the ability of ZP
M Wang et al.
Life sciences, 68(5), 525-537 (2001-02-24)
Acyl glucuronides are reactive electrophilic metabolites of carboxylate drugs, capable of undergoing hydrolysis, rearrangement and covalent binding reactions with proteins in vivo. Such covalent drug-protein adducts may be prerequisites for certain idiosyncratic immune and toxic responses in susceptible individuals. The
M J Bailey et al.
Chemico-biological interactions, 115(2), 153-166 (1998-11-25)
Drugs possessing a carboxylate functional group usually form acyl glucuronides as major metabolites. These electrophilic metabolites can undergo several spontaneous reactions, including covalent adduct formation with proteins. The present study examined whether covalent adducts were formed with microtubular protein (MTP
Min Wang et al.
Journal of gastroenterology and hepatology, 17(1), 66-71 (2002-03-16)
Zomepirac (ZP), a non-steroidal anti-inflammatory drug (NSAID), has been reported to cause immune-mediated liver injury. In vivo, ZP is metabolized to a chemically reactive acyl glucuronide conjugate (ZAG) which can undergo covalent adduct formation with proteins. Such acyl glucuronide-derived drug-protein
Qing Chen et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(1), 145-151 (2005-10-28)
Although zomepirac (ZP) and tolmetin (TM) induce anaphylactic reactions and form reactive acyl glucuronides, a direct link between the two events remains obscure. We report herein that, in addition to acyl glucuronidation, both drugs are subject to oxidative bioactivation. Following
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