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Merck

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
Quality level:
200

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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M J Bailey et al.
Journal of pharmacological and toxicological methods, 41(1), 27-32 (1999-10-03)
The covalent binding of drugs or their metabolites to proteins is of increasing interest in the investigation of the toxicity of these compounds. Recent attention on biological consequences of protein adduct formation with carboxylate drugs, derived via their reactive acyl
Jørgen Olsen et al.
Chemical research in toxicology, 18(11), 1729-1736 (2005-11-23)
Zomepirac [ZP, 5-(chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid] was withdrawn from the market because of unpredictable allergic reactions that may have been caused by ZP-protein adducts formed by reaction of the reactive acyl glucuronide of ZP (ZP-O-G) with endogenous proteins. To test the hypothesis
J Abraham
Social science & medicine (1982), 46(1), 39-51 (1998-02-17)
This article systematically examines government regulation of medicines in the U.K. and the U.S. with specific reference to carcinogenic risk assessment. By taking four non-steroidal anti-inflammatory drugs (NSAIDs) as case studies, it is argued that there have been inconsistencies between
M J Bailey et al.
Chemical research in toxicology, 9(3), 659-666 (1996-04-01)
Carboxylate drugs usually form acyl glucuronide conjugates as major metabolites. These electrophilic metabolites are reactive, capable of undergoing hydrolysis, rearrangement, and covalent binding reactions to proteins. The last-mentioned property has the potential to initiate immune and other toxic responses in
G R Cannell et al.
Life sciences, 70(1), 37-48 (2002-01-05)
Many nonsteroidal anti-inflammatory drugs (NSAIDs) which have antiproliferative activity in colon cancer cells are carboxylate compounds forming acyl glucuronide metabolites. Acyl glucuronides are potentially reactive, able to hydrolyse, rearrange into isomers, and covalently modify proteins under physiological conditions. This study
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