Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H13ClNO3.Na |
Molecular Weight | 313.711 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CN1C(CC([O-])=O)=CC(C)=C1C(=O)C2=CC=C(Cl)C=C2
InChI
InChIKey=SEEXPXUCHVGZGU-UHFFFAOYSA-M
InChI=1S/C15H14ClNO3.Na/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);/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H13ClNO3 |
Molecular Weight | 290.722 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Orally administered zomepirac and parenterally administered morphine. Comparison for the treatment of postoperative pain. | 1980 Nov 21 |
|
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 |
|
Zomepirac, interstitial nephritis, and renal failure. | 1982 Sep |
|
Nonoliguric renal failure associated with zomepirac. | 1983 Apr 1 |
|
Zomepirac-related acute renal failure. | 1983 Jan |
|
Renal failure and tubular dysfunction due to zomepirac therapy. | 1983 Jan 21 |
|
Zomepirac-induced renal failure. | 1983 Jun |
|
A zomepirac reaction mimicking ectopic pregnancy. | 1984 Jun |
|
Focal renal cortical necrosis associated with zomepirac. | 1984 Jun |
|
Interstitial nephritis, proteinuria, and renal failure caused by nonsteroidal anti-inflammatory drugs. Immunologic characterization of the inflammatory infiltrate. | 1984 Jun |
|
Interstitial nephritis and proteinuria associated with zomepirac. | 1984 Mar-Apr |
|
Nephrotoxicity from nonsteroidal anti-inflammatory drugs. | 1985 Mar |
|
Reversible renal failure and nephrotic syndrome without interstitial nephritis from zomepirac. | 1985 Oct |
|
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans. | 1993 Apr |
|
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. | 1993 Jan |
|
Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma. | 1994 Feb |
|
Dipeptidyl peptidase IV is a target for covalent adduct formation with the acyl glucuronide metabolite of the anti-inflammatory drug zomepirac. | 2001 Jan 5 |
|
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 |
|
India ink staining after sodium dodecyl sulfate polyacrylamide gel electrophoresis and in conjunction with Western blots for peptide mapping by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2002 |
|
Hepatic covalent adduct formation with zomepirac in the CD26-deficient mouse. | 2002 Jan |
|
Investigating the TNP-OVA and direct popliteal lymph node assays for the detection of immunostimulation by drugs associated with anaphylaxis in humans. | 2002 May-Jun |
|
Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile. | 2003 Nov |
|
Evaluation of a lymph node proliferation assay for its ability to detect pharmaceuticals with potential to cause immune-mediated drug reactions. | 2005 Jan 1 |
|
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. | 2005 Mar |
|
In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats. | 2005 Nov |
|
Pharmaceutical quality control of acid and neutral drugs based on competitive self-assembly in amphiphilic systems. | 2006 Jan |
|
Effect of drug utilization reviews on the quality of in-hospital prescribing: a quasi-experimental study. | 2006 Mar 14 |
|
Angioedema: clinical and etiological aspects. | 2007 |
|
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. | 2007 Jan 31 |
|
Determination of degradation pathways and kinetics of acyl glucuronides by NMR spectroscopy. | 2007 Jun |
|
Faecal blood loss with aspirin, nonsteroidal anti-inflammatory drugs and cyclo-oxygenase-2 selective inhibitors: systematic review of randomized trials using autologous chromium-labelled erythrocytes. | 2008 |
|
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery. | 2008 Oct 31 |
|
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. | 2009 Mar 16 |
|
Neuroprotective effects of zonisamide target astrocyte. | 2010 Feb |
|
The pharmacokinetic profile of a novel fixed-dose combination tablet of ibuprofen and paracetamol. | 2010 Jul 5 |
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.
Substance Class |
Chemical
Created
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admin
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Edited
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on
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Record UNII |
DA5B6IWF46
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Record Status |
Validated (UNII)
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Record Version |
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