Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:38:41 UTC
Update Date2024-10-09 21:41:26 UTC
Metabolite IDMMDBc0033197
Metabolite Identification
Common NamePyrazinecarboxamide
DescriptionPyrazinecarboxamide, also known as pyrazinamide, is only found in individuals that have used or taken this drug. It is a pyrazine that is used therapeutically as an antitubercular agent. Pyrazinecarboxamide is an important sterilizing prodrug that shortens tuberculosis (TB) therapy. However, the mechanism of action of pyrazinecarboxamide is poorly understood because of its unusual properties. In literature it has been written that the pyrazinoic acid (POA), the active moiety of pyrazinecarboxamide, disrupted membrane energetics and inhibited membrane transport function at acid pH in Mycobacterium tuberculosis. The antimycobacterial activity appears to partly depend on conversion of the drug to POA. Susceptible strains of M. tuberculosis produce pyrazinamidase, an enzyme that deaminates pyrazinecarboxamide to POA, and the vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. Experimental evidence suggests that pyrazinecarboxamide diffuses into M. tuberculosis in a passive manner, is converted into POA by pyrazinamidase, and because of an inefficient efflux system, accumulates in huge amounts in the bacterial cytoplasm. The accumulation of POA lowers the intracellular pH to a suboptimal level that is likely to inactivate a vital target enzyme such as fatty acid synthase. Recent studies (2007) demonstrated that pyrazinecarboxamide and its analogs inhibit the activity of purified FAS I.
Structure
Synonyms
ValueSource
2-CarbamylpyrazineChEBI
2-PyrazinecarboxamideChEBI
PyrazinamidaChEBI
PyrazinamidumChEBI
Pyrazine carboxamideChEBI
PYRAZINE-2-carboxamideChEBI
PyrazineamideChEBI
Pyrazinoic acid amideChEBI
Pyrazinoate amideGenerator
PirazimidaHMDB
PirazinamidHMDB
PyrazinamdieHMDB
Pyrazine carboxylamideHMDB
PyrazinecarboxamideHMDB
Pyrazinecarboxylic acid amideHMDB
PZAHMDB
TisamidHMDB
PyrazinamideChEBI
Molecular FormulaC5H5N3O
Average Mass123.1127
Monoisotopic Mass123.043261797
IUPAC Namepyrazine-2-carboxamide
Traditional Namepyrazinamide
CAS Registry Number98-96-4
SMILES
NC(=O)C1=NC=CN=C1
InChI Identifier
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChI KeyIPEHBUMCGVEMRF-UHFFFAOYSA-N