Structure via PubChem · Public domain (PubChem)
zomepirac
Sign in to saveAlso known as 5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid, Zomepiracum, Zomax
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by doctors in many situations and obtained a large share of the analgesics market; however, it was subsequently withdrawn in March 1983 due to its tendency to cause serious anaphylaxis in a small, but unpredictable, subset of the patient population.
Chemical data
- Formula
- C15H14ClNO3
- Molecular weight
- 291.73 g/mol
- IUPAC name
- 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
- SMILES
- CC1=C(N(C(=C1)CC(=O)O)C)C(=O)C2=CC=C(C=C2)Cl
- InChIKey
- ZXVNMYWKKDOREA-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 59.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1980
- Indications
- rheumatic disease
via ChEMBL · EBI
Research
268 papers- Zomepirac (Zomax).Drug and therapeutics bulletin · 1982
- Zomepirac (Zomax, McNeil Pharmaceutical).Drug intelligence & clinical pharmacy · 1981
- Evaluation of zomepirac sodium.American journal of hospital pharmacy · 1981
- Review of the pharmacokinetics and metabolism of zomepirac in man and animals.Journal of clinical pharmacology · 1980
- Zomepirac: a review of its pharmacological properties and analgesic efficacy.Drugs · 1982
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 291.066
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₅H₁₄ClNO₃
- canonical SMILES
- CC1=C(N(C(=C1)CC(=O)O)C)C(=O)C2=CC=C(C=C2)Cl
- defined daily dose
- 0.3
- subject has role
- non-steroidal anti-inflammatory drug
- Commons category
- Zomepirac
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
7 sectionsContents
- Indications
- Chemical structure
- Mechanism of action
- Anaphylaxis
- Synthesis
- See also
- References
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.
== Indications == Zomepirac was indicated for the management of mild to severe pain. 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 opioids. 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.
Excerpted from Wikipedia’s “zomepirac” article, available under the CC BY-SA 4.0 licence.