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- Withdrawn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
Structure for Zomepirac (DB04828)
- 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.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProstaglandin D2 receptor 2 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Zomepirac may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Zomepirac can be increased when it is combined with Abametapir. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Zomepirac is combined with Abciximab. Acebutolol Zomepirac may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Zomepirac is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Zomepirac is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Zomepirac is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Zomepirac. Acetohexamide The protein binding of Acetohexamide can be decreased when combined with Zomepirac. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Zomepirac. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Zomepirac sodium Y0185WZ209 64092-49-5 ZJXLSCXDGPDZOL-UHFFFAOYSA-M Zomepirac sodium anhydrous DA5B6IWF46 64092-48-4 SEEXPXUCHVGZGU-UHFFFAOYSA-M
Categories
- ATC Codes
- M01AB04 — Zomepirac
- Drug Categories
- Acetic Acid Derivatives and Related Substances
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Sensory System Agents
- 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
- External Links
- PubChem Compound
- 5733
- PubChem Substance
- 46504549
- ChemSpider
- 5531
- BindingDB
- 50027952
- 39994
- ChEBI
- 35859
- ChEMBL
- CHEMBL19490
- ZINC
- ZINC000000057537
- PharmGKB
- PA166049188
- PDBe Ligand
- ZOM
- Wikipedia
- Zomepirac
- PDB Entries
- 3r8h / 4jq3
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.026 mg/mL ALOGPS logP 3.37 ALOGPS logP 3.33 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 3.83 Chemaxon pKa (Strongest Basic) -7.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 59.3 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 77.2 m3·mol-1 Chemaxon Polarizability 29.68 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9714 Blood Brain Barrier + 0.8608 Caco-2 permeable + 0.7695 P-glycoprotein substrate Non-substrate 0.7316 P-glycoprotein inhibitor I Non-inhibitor 0.9347 P-glycoprotein inhibitor II Non-inhibitor 0.9287 Renal organic cation transporter Non-inhibitor 0.7965 CYP450 2C9 substrate Non-substrate 0.7288 CYP450 2D6 substrate Non-substrate 0.8163 CYP450 3A4 substrate Non-substrate 0.5337 CYP450 1A2 substrate Non-inhibitor 0.7776 CYP450 2C9 inhibitor Non-inhibitor 0.8844 CYP450 2D6 inhibitor Non-inhibitor 0.8955 CYP450 2C19 inhibitor Non-inhibitor 0.7741 CYP450 3A4 inhibitor Non-inhibitor 0.8973 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8525 Ames test Non AMES toxic 0.8817 Carcinogenicity Non-carcinogens 0.8425 Biodegradation Not ready biodegradable 0.9476 Rat acute toxicity 2.7638 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9389 hERG inhibition (predictor II) Non-inhibitor 0.8816
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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
- 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
- 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]
- 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 at September 11, 2007 20:33 / Updated at April 07, 2023 13:29