Pyrazinoic acid
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Pyrazinoic acid
Names
Identifiers
Properties
Hazards
Preferred IUPAC name
Pyrazine-2-carboxylic acid
- 98-97-5 checkY
3D model (JSmol)
ChEBI
- CHEBI:71311 ☒N
ChemSpider
- 1018 checkY
UNII
- 2WB23298SP checkY
- InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9) checkYKey: 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
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
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).
Chemical compound
Pyrazinoic acid is a pyrazinamide metabolite.
Possible role in tuberculosis treatment
[edit ]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]
References
[edit ]- ^ a b 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.
- ^ 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.201312005. PMC 4142361 . PMID 25161383.
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