Pyrazinoic acid

Pyrazinoic acid is a pyrazinamide metabolite.

Pyrazinoic acid
Skeletal formula of pyrazinoic acid
Space-filling model of the pyrazinoic acid molecule
Names
Preferred IUPAC name
Pyrazine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.471
MeSH Pyrazinoic+acid
UNII
  • InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9) checkY
    Key: NIPZZXUFJPQHNH-UHFFFAOYSA-N checkY
  • InChI=1/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
    Key: NIPZZXUFJPQHNH-UHFFFAOYAS
  • O=C(O)c1nccnc1
Properties
C5H4N2O2
Molar mass 124.10 g/mol
Appearance white to off white crystalline powder
Density 1.403g/cm3
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
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Possible role in tuberculosis treatment

Pyrazinamid is currently used as a treatment for tuberculosis. Mycobacterium tuberculosis converts pyrazinamid into pyrazinoic acid.[1] The use of pyrazinoic acid has been investigated as a possible treatment for pyrazinamid resistant strains of Mycobacterium tuberculosis.[1] 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.[2]

Derivatives/uses

It is a part of the bortezomib molecule.

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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