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Pyrazinoic acid

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Pyrazinoic acid
Skeletal formula of pyrazinoic acid
Space-filling model of the pyrazinoic acid molecule
Names
Preferred IUPAC name Pyrazine-2-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.471 Edit this at Wikidata
MeSH Pyrazinoic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)Key: NIPZZXUFJPQHNH-UHFFFAOYSA-N
  • InChI=1/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)Key: NIPZZXUFJPQHNH-UHFFFAOYAS
SMILES
  • O=C(O)c1nccnc1
Properties
Chemical formula C5H4N2O2
Molar mass 124.10 g/mol
Appearance white to off white crystalline powder
Density 1.403g/cm
Melting point 222 to 225 °C (432 to 437 °F; 495 to 498 K)
Boiling point 313.1 °C (595.6 °F; 586.2 K) at 760 mmHg
Solubility in water soluble in cold water
Acidity (pKa) 2.9
Hazards
Flash point 143.1 °C (289.6 °F; 416.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pyrazinoic acid is a pyrazinamide metabolite.

Possible role in tuberculosis treatment

Pyrazinamid is currently used as a treatment for tuberculosis. Mycobacterium tuberculosis converts pyrazinamid into pyrazinoic acid. The use of pyrazinoic acid has been investigated as a possible treatment for pyrazinamid resistant strains of Mycobacterium tuberculosis. It has been shown that the MICs of esters of pyrazinoic acid are lower, therefore they are more potent antibiotics. Moreover, they cross the bacterial membrane more easily, due to their higher lipophilicity.

References

  1. ^ Njire, Moses; Wang, Na; Wang, Bangxing; Tan, Yaoju; Cai, Xingshan; Liu, Yanwen; Mugweru, Julius; Guo, Jintao; Hameed, H. M. Adnan; Tan, Shouyong; Liu, Jianxiong; Yew, Wing Wai; Nuermberger, Eric; Lamichhane, Gyanu; Liu, Jinsong; Zhang, Tianyu (1 July 2017). "Pyrazinoic acid inhibits a bifunctional enzyme in Mycobacterium tuberculosis". Antimicrobial Agents and Chemotherapy. 61 (7). doi:10.1128/AAC.00070-17. PMC 5487608. PMID 28438933.
  2. Fernandes, João Paulo-dos Santos; Pavan, Fernando Rogerio; Leite, Clarice Queico Fujimura; Felli, Veni Maria Andres (2014). "Synthesis and evaluation of a pyrazinoic acid prodrug in Mycobacterium tuberculosis". Saudi Pharmaceutical Journal. 22 (4): 376–380. doi:10.1016/j.jsps.2013.12.005. PMC 4142361. PMID 25161383.


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