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Z2625

Sigma-Aldrich

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
EC Number:
264-669-2
MDL number:
MFCD00057223
UNSPSC Code:
12161501
PubChem Substance ID:
24902176
NACRES:
NA.77

SMILES string

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

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

InChI key

SEEXPXUCHVGZGU-UHFFFAOYSA-M

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

Signal Word

Danger

Hazard Statements

H300,H311 + H331

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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Zomepirac [ZP, 5-(chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid] was withdrawn from the market because of unpredictable allergic reactions that may have been caused by ZP-protein adducts formed by reaction of the reactive acyl glucuronide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.
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
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
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
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