Pyrazinoic acid

Pyrazinoic acid
Skeletal formula of pyrazinoic acid	Space-filling model of the pyrazinoic acid molecule
Names
	IUPAC name pyrazine-2-carboxylic acid
Identifiers
CAS Number	98-97-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:71311 ;
ChEMBL	ChEMBL613 ;
ChemSpider	1018 ;
ECHA InfoCard	100.002.471
MeSH	Pyrazinoic+acid
PubChem CID	1047;
UNII	2WB23298SP ;
CompTox Dashboard (EPA)	DTXSID30243367 ;
	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/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
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 [77 °F], 100 kPa).
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	Infobox references

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]

Derivatives/uses

It is a part of the bortezomib molecule.

References

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. 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.

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[Njire_et_al_2017-1] 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. 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.