Overview
| Generic Names: | PZA; Pirazimida; Pirazinamid; Pyrazinamdie; Pyrazine carboxylamide; Pyrazineamide; Pyrazinecarboxamide; Pyrazinecarboxylic acid amide; Pyrazinoic acid amide |
|---|---|
| IUPAC Name: | pyrazine-2-carboxamide |
| Trade Names: | Aldinamid; Aldinamide; Braccopiral; Corsazinmid; Dipimide; Eprazin; Farmizina; Isopas; Lynamide; Novamid; Pezetamid; Piraldina; Pirilene; Prazina; Pyrafat; Pyramide; Pyrazide; Pyrazinamide BP 2000; Rifater; Rozide; Tebrazid; Tebrazio; Unipyranamide; Zinamide; Zinastat; pms-Pyrazinamide |
| Brand Mixtures: | Rifater - Tab (Isoniazid + Pyrazinamide + Rifampin) |
| PharmGKB Accession Id: | PA451182 |
Description
A pyrazine that is used therapeutically as an antitubercular agent. [PubChem]
Indication
For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.
ATC Therapeutic Category
- J04AK:Other drugs for treatment of tuberculosis
Pharmacology and Interactions
Mechanism Of Action
Pyrazinamide is an important sterilizing drug that shortens tuberculosis (TB) therapy. However, the mechanism of action of pyrazinamide is poorly understood because of its unusual properties. In literature it has been written that the pyrazinoic acid (POA), the active moiety of pyrazinamide, disrupted membrane energetics and inhibited membrane transport function at acid pH in Mycobacterium tuberculosis. The antimycobacterial activity appears to partly depend on conversion of the drug to POA. Susceptible strains of M. tuberculosis produce pyrazinamidase, an enzyme that deaminates pyrazinamide to POA, and the vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. Experimental evidence suggests that pyrazinamide diffuses into M. tuberculosis in a passive manner, is converted into POA by pyrazinamidase, and because of an inefficient efflux system, accumulates in huge amounts in the bacterial cytoplasm. The accumulation of POA lowers the intracellular pH to a suboptimal level that is likely to inactivate a vital target enzyme such as fatty acid synthase.
Pharmacology
Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH.
Food Interactions
Take without regard to meals.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic.
Protein Binding
~10% (bound to plasma proteins)
Absorption
Rapidly and well absorbed from the gastrointestinal tract.
Half Life
9-10 hours (normal conditions)
Toxicity
Side effects include liver injury, arthralgias, anorexia, nausea and vomiting, dysuria,malaise and fever, sideroblastic anemia, adverse effects on the blood clotting mechanism or vascular integrity, and hypersensitivity reactions such as urticaria, pruritis and skin rashes.
Chemical Properties
Chemical Formula:
C5H5N3O
SMILES Code:
c1cnc(cn1)C(=O)N
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
123.1127 / 123.0433
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
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XDH |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| cyclosporine | Pyrazinamide decreases the effect of cyclosporine |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
|---|---|---|---|
|
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Toxic liver disease |
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Publications |
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Tuberculosis |
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Publications |
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xanthinuria |
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Publications |
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.