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
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)
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7018870 |
15.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZOMAX Approved UseZOMAX is indicated for all forms of mild to moderately severe pain. Launch Date1979 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.94 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.47 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1102.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
494.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
232.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOMEPIRAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 6 times / day multiple, oral Dose: 100 mg, 6 times / day Route: oral Route: multiple Dose: 100 mg, 6 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Age Group: 28 years Sex: F Population Size: 1 Sources: |
Disc. AE: Renal insufficiency... AEs leading to discontinuation/dose reduction: Renal insufficiency (1 patient) Sources: |
300 mg 1 times / day multiple, oral Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy, 36-72 years n = 2 Health Status: unhealthy Age Group: 36-72 years Sex: F Population Size: 2 Sources: |
Disc. AE: Renal insufficiency... AEs leading to discontinuation/dose reduction: Renal insufficiency (2 patients) Sources: |
800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: |
unhealthy n = 10 Health Status: unhealthy Condition: opioid abuse Population Size: 10 Sources: |
Other AEs: Backache, Nausea... Other AEs: Backache (2 patients) Sources: Nausea (2 patients) Churning of stomach (2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Renal insufficiency | 1 patient Disc. AE |
100 mg 6 times / day multiple, oral Dose: 100 mg, 6 times / day Route: oral Route: multiple Dose: 100 mg, 6 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Age Group: 28 years Sex: F Population Size: 1 Sources: |
Renal insufficiency | 2 patients Disc. AE |
300 mg 1 times / day multiple, oral Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy, 36-72 years n = 2 Health Status: unhealthy Age Group: 36-72 years Sex: F Population Size: 2 Sources: |
Backache | 2 patients | 800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: |
unhealthy n = 10 Health Status: unhealthy Condition: opioid abuse Population Size: 10 Sources: |
Churning of stomach | 2 patients | 800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: |
unhealthy n = 10 Health Status: unhealthy Condition: opioid abuse Population Size: 10 Sources: |
Nausea | 2 patients | 800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: |
unhealthy n = 10 Health Status: unhealthy Condition: opioid abuse Population Size: 10 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 6.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 6.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Clinical analgesic assay of oral zomepirac and intramuscular morphine. | 1979 |
|
Long-term safety of zomepirac: a double-blind comparison with aspirin in patients with osteoarthritis. | 1980 May-Jun |
|
Anaphylactic shock, acute renal failure, and disseminated intravascular coagulation. Suspected complications of zomepirac. | 1982 Feb 26 |
|
Reversible nonoliguric acute renal failure associated with zomepirac therapy. | 1982 Jun |
|
A zomepirac reaction mimicking ectopic pregnancy. | 1984 Jun |
|
Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma. | 1994 Feb |
|
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg. | 2001 Jan 10 |
|
Inhibition of proliferation of HT-29 colon adenocarcinoma cells by carboxylate NSAIDs and their acyl glucuronides. | 2001 Nov 21 |
|
HPLC/1H NMR spectroscopic studies of the reactive alpha-1-O-acyl isomer formed during acyl migration of S-naproxen beta-1-O-acyl glucuronide. | 2001 Oct |
|
Photolysis of NSAIDs. IV. Photoproducts of zomepirac determined by LC-ESI-MS. | 2004 Dec |
|
In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats. | 2005 Nov |
|
Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states. | 2006 Feb |
|
Evidence for the bioactivation of zomepirac and tolmetin by an oxidative pathway: identification of glutathione adducts in vitro in human liver microsomes and in vivo in rats. | 2006 Jan |
|
Determination of degradation pathways and kinetics of acyl glucuronides by NMR spectroscopy. | 2007 Jun |
|
Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update. | 2007 Mar 15 |
|
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
Neuroprotective effects of zonisamide target astrocyte. | 2010 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7018870
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6133523
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.
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C257
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)