Pyrazinoic acid

Pyrazinoic acid is a pyrazinamide metabolite.

Pyrazinoic acid

Names
Preferred IUPAC name Pyrazine-2-carboxylic acid
Identifiers
CAS Number	98-97-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:71311 N
ChEMBL	ChEMBL613 Y
ChemSpider	1018 Y
ECHA InfoCard	100.002.471
MeSH	Pyrazinoic+acid
PubChem CID	1047
UNII	2WB23298SP Y
CompTox Dashboard (EPA)	DTXSID30243367
InChI InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9) Y Key: NIPZZXUFJPQHNH-UHFFFAOYSA-N Y 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). N verify (what is YN ?) 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]