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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14ClNO3
Molecular Weight 291.73
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOMEPIRAC

SMILES

CN1C(CC(O)=O)=CC(C)=C1C(=O)C2=CC=C(Cl)C=C2

InChI

InChIKey=ZXVNMYWKKDOREA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H14ClNO3
Molecular Weight 291.73
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Zomepirac Sodium (Zomax) is a pyrrole-acetic acid structurally related to tolmetin sodium. Zomepirac is a prostaglandin synthetase inhibitor and is not an opioid, an opioid antagonist, or a salicylate. Zomepirac was approved by the Food and Drug Administration for marketing in the United States as an analgesic. It was indicated for all forms of mild to moderately severe pain, and was being promoted as a "comprehensive, non-addicting analgesic." Later Zomepirac was found to be associated with fatal and near-fatal anaphylactoid reactions. The manufacturer voluntarily removed Zomax tablets from the Canadian, US, and UK markets in March 1983.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
15.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZOMAX

Cmax

ValueDoseCo-administeredAnalytePopulation
7.94 μg/mL
200 mg single, oral
ZOMEPIRAC plasma
Homo sapiens
4.42 μg/mL
100 mg single, oral
ZOMEPIRAC plasma
Homo sapiens
2.47 μg/mL
50 mg single, oral
ZOMEPIRAC plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1102.7 μg × h/mL
200 mg single, oral
ZOMEPIRAC plasma
Homo sapiens
494.4 μg × h/mL
100 mg single, oral
ZOMEPIRAC plasma
Homo sapiens
232.7 μg × h/mL
50 mg single, oral
ZOMEPIRAC plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The oral dose of zomepirac for mild to moderately severe pain is 50-100 mg every four to six hours. In acute moderate to severe pain in adults, a 100-mg dose would be reasonable initial therapy. In chronic pain situations, the 50-mg dose may be as effective in some patients as the 100-mg dose. Doses of more than 100 mg are not recommended.
Route of Administration: Oral
In Vitro Use Guide
Zomepirac failed to displace tritiated etorphine significantly at concentrations up to 200 umol/l. It was active (3-7 X 10(-5) mol/l) on both the electrically stimulated guinea pig ileum and mouse vas deferens but was less efficacious than morphine; these effects were not reversed by narcotic antagonists.
Substance Class Chemical
Record UNII
822G987U9J
Record Status Validated (UNII)
Record Version