2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetic acid

• ChemBase ID: 4372
• Molecular Formular: C15H14ClNO3
• Molecular Mass: 291.72956
• Monoisotopic Mass: 291.06622099
• SMILES: Clc1ccc(C(=O)c2n(c(cc2C)CC(=O)O)C)cc1
• Canonical SMILES: OC(=O)Cc1cc(c(n1C)C(=O)c1ccc(cc1)Cl)C
• 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)
• InChIKey: ZXVNMYWKKDOREA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetic acid
• IUPAC Traditional name: [5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
• Synonyms: 5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid; Zomepirac sodium; Zomepiracum [inn-latin]; Zomepirac

Database IDs

• CAS Number: 33369-31-2
• PubChem SID: 160967804; 46504549
• PubChem CID: 5733

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8570757
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6842828
• LogD (pH = 7.4): 0.096137345
• Log P: 3.3313756
• Molar Refractivity: 77.1976 cm^3
• Polarizability: 29.303864 Å^3
• Polar Surface Area: 59.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.37
• LOG S: -4.05
• Solubility (Water): 2.60e-02 g/l

DETAILS

DrugBank - DB04828

• Drug Groups: withdrawn
• 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.
• Indication: Zomepirac was indicated for the management of mild to severe pain.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia