Pyrazinoic acid
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| Names | |||
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| Preferred IUPAC name Pyrazine-2-carboxylic acid | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEMBL | |||
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| ECHA InfoCard | 100.002.471 | ||
| MeSH | Pyrazinoic+acid | ||
PubChem CID |
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CompTox Dashboard (EPA) |
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| 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). | |||
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.[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
- ^ 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.2013.12.005. PMC 4142361. PMID 25161383.