P7136

Pyrazinecarboxamide

• Synonym(s): Pyrazinamide, Pyrazinoic acid amide
• Empirical Formula (Hill Notation): C₅H₅N₃O
• CAS Number: 98-96-4
• Molecular Weight: 123.11
• UNSPSC Code: 41116107
• NACRES: NA.85
• PubChem Substance ID: 24278648
• EC Number: 202-717-6
• Beilstein/REAXYS Number: 112306
• MDL number: MFCD00006132

Properties

• form: powder
• Quality Segment: 200
• mp: 189-191 °C (lit.)
• antibiotic activity spectrum: mycobacteria
• mode of action: cell membrane | interferes
• SMILES string: NC(=O)c1cnccn1
• InChI: 1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
• InChI key: IPEHBUMCGVEMRF-UHFFFAOYSA-N

Description

Application

Pyrazinamide is used therapeutically as an antitubercular agent. Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits. It is used to study liver toxicity prevention [1] and mechanisms of resistance [2].

Biochem/physiol Actions

The active moiety of pyrazinamide is pyrazinoic acid (POA). POA is thought to disrupt membrane energetics and inhibit membrane transport function at acid pH in Mycobacterium tuberculosis. Iron enhances the antituberculous activity of pyrazinamide [3]. Pyrazinamide and its analogs have been shown to inhibit the activity of purified FAS I.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)