pyrazinoic

Pyrazinoic is an adjective used in chemistry to refer to anything derived from or related to pyrazine-2-carboxylic acid, commonly called pyrazinoic acid. In systematic naming, compounds described as pyrazinoic include the parent acid itself as well as its derivatives, such as esters, amides, and salts, collectively known as pyrazinoates. The term is used to denote the pyrazine ring bearing a carboxyl group, typically at the 2-position, forming the basis for multiple substituted or functionalized compounds.

The core structure of pyrazinoic-related compounds is a pyrazine ring with a carboxyl substituent. This framework serves as a versatile scaffold in medicinal and agricultural chemistry, enabling various transformations such as esterification, amidation, and salt formation to tailor properties like polarity, solubility, and biological activity.

Pharmacological relevance is most notable in relation to pyrazinamide, a drug used to treat tuberculosis. Pyrazinamide is a prodrug that is hydrolyzed by mycobacterial enzymes to pyrazinoic acid, the active moiety that contributes to antibacterial effect under acidic conditions. The exact mechanism of action of pyrazinoic acid in Mycobacterium tuberculosis is the subject of ongoing study and involves disruption of energy production and membrane processes at low pH.

In synthesis and naming, pyrazinoic compounds are prepared or modified through standard carboxylate chemistry, including conversion to esters, amides, or salts, and can be further derivatized at other positions on the pyrazine ring. See also pyrazine, pyrazinamide, and pyrazine-2-carboxylic acid.