Zomepirac

HCID 5733

Substructure search Find similar structures

Basic information

CAS: 33369-31-2
Standard SMILES: Cc1cc(CC(=O)O)n(C)c1C(=O)c1ccc(Cl)cc1
InChIKey: ZXVNMYWKKDOREA-UHFFFAOYSA-N
Molecular formula: C15H14ClNO3
Average molar mass: 291.73 g/mol
Monoisotopic mass: 291.06622099

Overview

Zomepirac is a monocarboxylic acid, a member of pyrroles, an aromatic ketone and a member of monochlorobenzenes. It has a role as a non-steroidal anti-inflammatory drug and a cardiovascular drug. It is functionally related to an acetic acid.

Names & identifiers

Preferred name: Zomepirac
IUPAC: 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
English name: zomepirac
Molecular formula: C15H14ClNO3
Molecular weight: 291.73

Names & synonyms

zomepirac33369-31-25-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acidZomepiracumZomepiraco[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetic acid822G987U9JDTXSID9023754CHEBI:35859(5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl)acetic acidRefChem:905377DTXCID803754

Show more names

Zomepirac free acidZXVNMYWKKDOREA-UHFFFAOYSA-N1H-Pyrrole-2-acetic acid, 5-(4-chlorobenzoyl)-1,4-dimethyl-2-(5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl)acetic acid

M01AB045-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate dihydrate251-474-22-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acidCHEMBL194901H-Pyrrole-2-aceticacid, 5-(4-chlorobenzoyl)-1,4-dimethyl-Zomepiracum [INN-Latin]1,4-Dimethyl-5-p-chlorobenzoylpyrrole-2-acetic acid

Database identifiers

CAS: 33369-31-2、64092-49-5
PubChem CID: 5733
DTXSID: DTXSID9023754
ChEMBL: CHEMBL19490
ChEBI: CHEBI:35859
UNII: 822G987U9J
EC Number: 251-474-2
Nikkaji: J21.385C

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 59.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 20
Formal charge: 0
Complexity: 379

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Human DrugsPharmaceuticals

Collision Cross Section170.44 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 178 · 178-179°
Boiling point: 470.8 · 470.8±45.0 °C(Predicted)
Density: 1.28 · 1.28±0.1 g/cm3(Predicted)
solubility: Methanol (Sparingly), Water (Slightly)
pka: 4.57 · pKa 4.57(H2O-EtOH (1:1 v/v)) (Uncertain)
form: Solid
color: Off-White to Yellow
Stability: Hygroscopic
FDA UNII: 822 G987U9J · 822G987U9J
ATC code: 1 AB04 · M01AB04

Safety & regulation

Hazard information

Other Safety InformationIMAP assessments - 1H-Pyrrole-2-acetic acid, 5-(4-chlorobenzoyl)-1,4-dimethyl-: Environment tier I assessment

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

zomepirac

DILI Negative

DOI:10.1016/j.drudis.2019.09.022

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

Metabolism/MetabolitesZomepirac has known human metabolites that include Zomepirac O-glucuronide.

MeSH Pharmacological Classification · 1 item

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

UsesZomepirac is an analgesic, anti-inflammatory drug.

Upstream & downstream products

Upstream raw materials

Sodium hydroxide Hydrochloric acid

Suppliers5 total

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]

上海陶术生物科技股份有限公司13564774135 · [email protected]

TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]

湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Zomepirac is a member of pyrroles, a member of monochlorobenzenes, a monocarboxylic acid and an aromatic ketone. It has a role as a non-steroidal anti-inflammatory drug and a cardiovascular drug. It is functionally related to an acetic acid.