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Identification
NameZomepirac
Accession NumberDB04828
TypeSmall Molecule
GroupsWithdrawn
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acidNot AvailableNot Available
ZomepiracumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Zomepirac sodium
Thumb
  • InChI Key: SEEXPXUCHVGZGU-UHFFFAOYSA-M
  • Monoisotopic Mass: 313.048165669
  • Average Mass: 313.711
DBSALT000335
Categories
CAS number33369-31-2
WeightAverage: 291.73
Monoisotopic: 291.066221026
Chemical FormulaC15H14ClNO3
InChI KeyZXVNMYWKKDOREA-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Acetophenone
  • Aryl ketone
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Substituted pyrrole
  • N-methylpyrrole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Pyrrole
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationZomepirac was indicated for the management of mild to severe pain.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8844
CYP450 2D6 substrateNon-inhibitor0.8955
CYP450 2C19 substrateNon-inhibitor0.7741
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point178.5 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Prostaglandin D2 receptor 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prostaglandin D2 receptor 2 Q9Y5Y4 Details

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. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
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Drug created on September 11, 2007 14:33 / Updated on September 16, 2013 17:25