Zomepirac
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Zomepirac
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CAS No:
33369-31-2
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Formula:
C15H14ClNO3
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Chemical Name:
Zomepirac
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Synonyms:
1H-Pyrrole-2-acetic acid,5-(4-chlorobenzoyl)-1,4-dimethyl-;Pyrrole-2-acetic acid,5-(p-chlorobenzoyl)-1,4-dimethyl-;5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid;5-(4-Chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid;Zomepirac;1,4-Dimethyl-5-p-chlorobenzoylpyrrole-2-acetic acid;Zomiperac
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CAS No:
Description
Zomepirac is a member of pyrroles, a member of monochlorobenzenes, a monocarboxylic acid and an aromatic ketone. It has a role as a non-steroidal anti-inflammatory drug and a cardiovascular drug. It derives from an acetic acid.|Zomepirac, formerly marketed as Zomax tablets, was associated with fatal and near-fatal anaphylactoid reactions. The manufacturer voluntarily removed Zomax tablets from the Canadian, US, and UK markets in March 1983.
Zomepirac Basic Attributes
291.73
291.73
251-474-2
822G987U9J
757379
DTXSID9023754
M - Musculo-skeletal system
2933990090
Characteristics
59.30000
2.84500
1.28g/cm3
178.5 °C
470.8ºC at 760mmHg
238.5ºC
1.595
pKa 4.57(H2O-EtOH (1:1 v/v)) (Uncertain)
Drug Information
Zomepirac was indicated for the management of mild to severe pain.
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)
Zomepirac has known human metabolites that include Zomepirac O-glucuronide.
5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate dihydrate
Zomepirac Use and Manufacturing
5-(p-Chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2-acetic acid: A suspension of 17.3 g (0.0435 mol) of ethyl 5-(p-chlorobenzoyl)-1,4-dimethyl- 3-ethoxypyrrole-2-acetate in 170 g of 25% hydroxide is heated under reflux for 3 hours. The suspension is poured into ice and the resulting yellow solution is added to ice-hydrochloric acid with stirring. The precipitated solid is collected by filtration, air dried and recrystallized from acetone containing 10% water to give 5-(p-chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2-acetic acid as a white solid; melting point 253°C to 254°C. Ethyl 5-(p-chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2-acetate: A suspension of 2.0 g of 5-(p-chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2- acetic acid in 20 ml of 0.5% ethanolic hydrogen chloride is heated under reflux. The solid gradually dissolves. After 40 minutes a white crystalline solid precipitates. The solution is cooled and the solid product, ethyl 5-(p- chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2-acetate, is filtered and dried, melting point 197°C to 198°C. Ethyl 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate: A 9.0 g (0.0255 mol) sample of ethyl 5-(p-chlorobenzoyl)-3-carboxy-1,4-dimethylpyrrole-2- acetate is heated under nitrogen at 210°C to 230°C for 2 hours. Gas is evolved. The residue is molecularly distilled in a sublimator at 195°C, 0.05 mm/Hg. The sublimate is recrystallized from cyclohexane to give ethyl 5-(p- chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate as a white solid, melting point 107°C to 109°C. 5-(p-Chlorobenzoyl)-1,-4dimethylpyrrole-2-ecetic acid: A suspension of 4.0 g (0.0125 mol) of ethyl 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate in 26 ml of 0.5 N sodium hydroxide (0.013 mol) is heated under reflux for 30 minutes. The resulting solution is acidified with dilute hydrochloric acid, and the precipitated solid is collected by filtration, air dried and recrystallized from 2-propanol to give 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid as a white crystalline solid, melting point 178°C to 179°C.
Pharmaceuticals
Computed Properties
Molecular Weight:291.73
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:291.0662210
Monoisotopic Mass:291.0662210
Topological Polar Surface Area:59.3
Heavy Atom Count:20
Complexity:379
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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