Zomepirac

drugbox
IUPAC_name = 2- [5-(4-chlorobenzoyl)-1,4-dimethyl-pyrrol-2-yl] acetic acid

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CAS_number = 33369-31-2
ATC_prefix =M01
ATC_suffix =AB04
ATC_supplemental =
PubChem = 5733
DrugBank =
C=15 | H=14 | Cl=1 | N=1 | O=3
molecular_weight = 291.729 g/mol
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
pregnancy_category =
legal_status = "withdrawn"
routes_of_administration = oral
excretion =

Zomepirac is an orally effective NSAID that has antipyretic actions. It was developed by McNeil Pharmaceutical and 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by doctors in many situations and obtained a large share of the anagesics market; however, it was subsequently withdrawn in March 1983 due to its tendency to cause serious anaphylaxis in an unpredictable subset of the patient population. [Peter H. Rheinstein, [http://www.findarticles.com/p/articles/mi_m3225/is_n3_v46/ai_12645044 Reporting of adverse drug events: a key to postmarketing drug safety] , "American Family Physician", Sept, 1992] [Mark P. Grillo and Fengmei Hua, [http://dmd.aspetjournals.org/cgi/content/full/31/11/1429 IDENTIFICATION OF ZOMEPIRAC-S-ACYL-GLUTATHIONE IN VITRO IN INCUBATIONS WITH RAT HEPATOCYTES AND IN VIVO IN RAT BILE] , "Drug Metabolism and Disposition", August 19, 2003]

Indications

Zomepirac was indicated for the management of mild to severe pain.cite journal |author=Lewis JR |title=Zomepirac sodium. A new nonaddicting analgesic |journal=JAMA |volume=246 |issue=4 |pages=377–9 |year=1981 |pmid=7241789 |doi=] Multiple clinical trials demonstrated zomepirac to be more effective than aspirin or codeine alone and to be as effective as analgesic combinations containing codeine or other narcotics. [cite journal |author=Steele CE, Jefferson WL |title=A multi-centre study of zomepirac in painful conditions: an analysis of clinical data for 15,484 patients |journal=Current medical research and opinion |volume=8 |issue=6 |pages=382–91 |year=1983 |pmid=6221886 |doi=] [cite journal |author=Mehlisch DR, Joy ED |title=Zomepirac sodium vs APC with codeine for oral surgery pain |journal=Journal of oral surgery (American Dental Association : 1965) |volume=39 |issue=6 |pages=426–9 |year=1981 |pmid=7014804 |doi=] [cite journal |author=Stambaugh JE, Sarajian C |title=Analgesic efficacy of zomepirac sodium in patients with pain due to cancer |journal=Journal of clinical pharmacology |volume=21 |issue=11-12 Pt 1 |pages=501–7 |year=1981 |pmid=7037868 |doi=] [cite journal |author=Evans PJ, McQuay HJ, Rolfe M, O'Sullivan G, Bullingham RE, Moore RA |title=Zomepirac, placebo and paracetamol/dextropropoxyphene combination compared in orthopaedic postoperative pain |journal=British journal of anaesthesia |volume=54 |issue=9 |pages=927–33 |year=1982 |pmid=7052110 |doi=] [cite journal |author=Baird WM, Turek D |title=Comparison of zomepirac, APC with codeine, codeine and placebo in the treatment of moderate and severe postoperative pain |journal=Journal of clinical pharmacology |volume=20 |issue=4 Pt 2 |pages=243–9 |year=1980 |pmid=6991540 |doi=] [cite journal |author=Mehlisch DR, Joy ED, Moore TE, Porter K, Stumpf AJ, Wolfe SH |title=Clinical comparison of zomepirac with APC/codeine combination in the treatment of pain following oral surgery |journal=Journal of clinical pharmacology |volume=20 |issue=4 Pt 2 |pages=271–8 |year=1980 |pmid=6991544 |doi=] [cite journal |author=Diamond S, Medina JL |title=A double-blind study of zomepirac sodium and placebo in the treatment of muscle contraction headache |journal=Headache |volume=21 |issue=2 |pages=45–8 |year=1981 |pmid=7016809 |doi=] Zomepirac provided analgesia comparable with usual intramuscular doses of morphine in postoperative pain and that with long-term use, neither tolerance to its analgesic effect nor psychological or physical dependence had been demonstrated. [cite journal |author=Wallenstein SL, Rogers A, Kaiko RF, Heidrich G, Houde RW |title=Relative analgesic potency of oral zomepirac and intramuscular morphine in cancer patients with postoperative pain |journal=Journal of clinical pharmacology |volume=20 |issue=4 Pt 2 |pages=250–8 |year=1980 |pmid=6991541 |doi=]

Chemical structure

Zomepirac is the sodium salt of 5-(4-chlorobenzoyl)-1,4 dimethyl-1H-pyrrole-2-acetate dihydrate. It is a pyrrole-acetic acid which is structurally related to tolmetin.

Mechanism of action

It is a prostaglandin synthetase inhibitor. [DC McLeod, [http://www.theannals.com/cgi/content/abstract/15/7/522 Zomepirac (Zomax, McNeil Pharmaceutical)] , "Drug Intelligence & Clinical Pharmacy": Vol. 15, No. 7, pp. 522-530. ]

References