Zomepirac

Identification

Generic Name
Zomepirac
DrugBank Accession Number
DB04828
Background

Zomepirac, formerly marketed as Zomax tablets, was associated with fatal and near-fatal anaphylactoid reactions. The manufacturer voluntarily removed Zomax tablets from the Canadian, US, and UK markets in March 1983.

Type
Small Molecule
Groups
Withdrawn
Structure
Thumb
Weight
Average: 291.73
Monoisotopic: 291.066221026
Chemical Formula
C15H14ClNO3
Synonyms
  • 5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid
  • Zomepirac
  • Zomepiracum

Pharmacology

Indication

Zomepirac was indicated for the management of mild to severe pain.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProstaglandin D2 receptor 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirZomepirac may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Zomepirac can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Zomepirac is combined with Abciximab.
AbirateroneThe metabolism of Zomepirac can be decreased when combined with Abiraterone.
AcebutololZomepirac may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Zomepirac is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Zomepirac is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Zomepirac is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Zomepirac.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Zomepirac.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Zomepirac sodiumY0185WZ20964092-49-5ZJXLSCXDGPDZOL-UHFFFAOYSA-M
Zomepirac sodium anhydrousDA5B6IWF4664092-48-4SEEXPXUCHVGZGU-UHFFFAOYSA-M

Categories

ATC Codes
M01AB04 — Zomepirac
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl-phenylketones
Alternative Parents
Benzoyl derivatives / Chlorobenzenes / N-methylpyrroles / Aryl chlorides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Aryl-phenylketone / Azacycle / Benzenoid / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Chlorobenzene
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, monochlorobenzenes, aromatic ketone, pyrroles (CHEBI:35859)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
822G987U9J
CAS number
33369-31-2
InChI Key
ZXVNMYWKKDOREA-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetic acid
SMILES
CN1C(CC(O)=O)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1

References

Synthesis Reference

James B. Doherty, Debra L. Allison, "Process for the preparation of zomepirac and related compounds." U.S. Patent US4374997, issued January, 1978.

US4374997
General References
Not Available
PubChem Compound
5733
PubChem Substance
46504549
ChemSpider
5531
BindingDB
50027952
RxNav
39994
ChEBI
35859
ChEMBL
CHEMBL19490
ZINC
ZINC000000057537
PharmGKB
PA166049188
PDBe Ligand
ZOM
Wikipedia
Zomepirac
PDB Entries
3r8h / 4jq3

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.026 mg/mLALOGPS
logP3.37ALOGPS
logP3.33ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.2 m3·mol-1ChemAxon
Polarizability29.68 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9714
Blood Brain Barrier+0.8608
Caco-2 permeable+0.7695
P-glycoprotein substrateNon-substrate0.7316
P-glycoprotein inhibitor INon-inhibitor0.9347
P-glycoprotein inhibitor IINon-inhibitor0.9287
Renal organic cation transporterNon-inhibitor0.7965
CYP450 2C9 substrateNon-substrate0.7288
CYP450 2D6 substrateNon-substrate0.8163
CYP450 3A4 substrateNon-substrate0.5337
CYP450 1A2 substrateNon-inhibitor0.7776
CYP450 2C9 inhibitorNon-inhibitor0.8844
CYP450 2D6 inhibitorNon-inhibitor0.8955
CYP450 2C19 inhibitorNon-inhibitor0.7741
CYP450 3A4 inhibitorNon-inhibitor0.8973
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8525
Ames testNon AMES toxic0.8817
CarcinogenicityNon-carcinogens0.8425
BiodegradationNot ready biodegradable0.9476
Rat acute toxicity2.7638 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9389
hERG inhibition (predictor II)Non-inhibitor0.8816
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Prostaglandin j receptor activity
Specific Function
Receptor for prostaglandin D2 (PGD2). Coupled to the G(i)-protein. Receptor activation may result in pertussis toxin-sensitive decreases in cAMP levels and Ca(2+) mobilization. PI3K signaling is al...
Gene Name
PTGDR2
Uniprot ID
Q9Y5Y4
Uniprot Name
Prostaglandin D2 receptor 2
Molecular Weight
43267.15 Da
References
  1. Hata AN, Lybrand TP, Marnett LJ, Breyer RM: Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. Mol Pharmacol. 2005 Mar;67(3):640-7. Epub 2004 Nov 24. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Chen Q, Doss GA, Tung EC, Liu W, Tang YS, Braun MP, Didolkar V, Strauss JR, Wang RW, Stearns RA, Evans DC, Baillie TA, Tang W: 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. Drug Metab Dispos. 2006 Jan;34(1):145-51. doi: 10.1124/dmd.105.004341. Epub 2005 Oct 26. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Pritchard JF, O'Neill PJ, Affrime MB, Lowenthal DT: Influence of uremia, hemodialysis, and nonesterified fatty acids on zomepirac plasma protein binding. Clin Pharmacol Ther. 1983 Nov;34(5):681-8. [Article]
  2. Ojingwa JC, Spahn-Langguth H, Benet LZ: Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma. J Pharmacokinet Biopharm. 1994 Feb;22(1):19-40. [Article]

Drug created on September 11, 2007 20:33 / Updated on October 03, 2021 00:53