Zomepirac

Zomepirac
Clinical data
Routes of; administration	By mouth
ATC code	M01AB04 (WHO) ;
Legal status
Legal status	withdrawn;
Identifiers
	IUPAC name 2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-pyrrol-2-yl]acetic acid;
CAS Number	33369-31-2 ;
PubChem CID	5733;
DrugBank	DB04828 ;
ChemSpider	5531 ;
UNII	822G987U9J;
ChEBI	CHEBI:35859 ;
ChEMBL	ChEMBL19490 ;
CompTox Dashboard (EPA)	DTXSID9023754 ;
ECHA InfoCard	100.046.780
Chemical and physical data
Formula	C15H14ClNO3
Molar mass	291.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1c(cc(n1C)CC(=O)O)C)c2ccc(Cl)cc2;
	InChI InChI=1S/C15H14ClNO3/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) ; Key:ZXVNMYWKKDOREA-UHFFFAOYSA-N ;
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Zomepirac is an orally effective nonsteroidal anti-inflammatory drug (NSAID) that has antipyretic actions. It was developed by McNeil Pharmaceutical, approved by the FDA in 1980, and sold as the sodium salt zomepirac sodium, under the brand name Zomax. Due to its clinical effectiveness, it was preferred by doctors in many situations and obtained a large share of the analgesics market; however, it was subsequently withdrawn in March 1983 due to its tendency to cause serious anaphylaxis in a small, but unpredictable, subset of the patient population.^[1]^[2]

^ Rheinstein PH (September 1992). "Reporting of adverse drug events: a key to postmarketing drug safety". American Family Physician. 46 (3): 873–874. PMID 1514478.
^ Grillo MP, Hua F (November 2003). "Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile". Drug Metabolism and Disposition. 31 (11): 1429–1436. doi:10.1124/dmd.31.11.1429. PMID 14570776. S2CID 9912756.

[1] Rheinstein PH (September 1992). "Reporting of adverse drug events: a key to postmarketing drug safety". American Family Physician. 46 (3): 873–874. PMID 1514478.

[2] Grillo MP, Hua F (November 2003). "Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile". Drug Metabolism and Disposition. 31 (11): 1429–1436. doi:10.1124/dmd.31.11.1429. PMID 14570776. S2CID 9912756.

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[2]

Clinical data

Routes of administration	By mouth
ATC code	M01AB04 (WHO)
Legal status
Legal status	withdrawn
Identifiers
IUPAC name 2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-pyrrol-2-yl]acetic acid
CAS Number	33369-31-2^N
PubChem CID	5733
DrugBank	DB04828^Y
ChemSpider	5531^Y
UNII	822G987U9J
ChEBI	CHEBI:35859^Y
ChEMBL	ChEMBL19490^Y
CompTox Dashboard (EPA)	DTXSID9023754
ECHA InfoCard	100.046.780
Chemical and physical data
Formula	C₁₅H₁₄ClNO₃
Molar mass	291.73 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(c1c(cc(n1C)CC(=O)O)C)c2ccc(Cl)cc2
InChI InChI=1S/C15H14ClNO3/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)^Y Key:ZXVNMYWKKDOREA-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)