Drug/Small Molecule:
pyrazinamide

2D structure

Overview

Generic Names: PZA; Pirazimida; Pirazinamid; Pyrazinamdie; Pyrazine carboxylamide; Pyrazineamide; Pyrazinecarboxamide; Pyrazinecarboxylic acid amide; Pyrazinoic acid amide
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 (source: Drug Bank)

Indication

For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents. (source: Drug Bank)

ATC Therapeutic Category

  • J04AK:Other drugs for treatment of tuberculosis

Pharmacology, Interactions, and Contraindications

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 <i>Mycobacterium tuberculosis</i>. The antimycobacterial activity appears to partly depend on conversion of the drug to POA. Susceptible strains of <i>M. tuberculosis</i> 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 <i>M. tuberculosis</i> 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. (source: Drug Bank)

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 <i>Mycobacterium tuberculosis</i>. In vitro and in vivo, the drug is active only at a slightly acid pH. (source: Drug Bank)

Food Interactions

Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. (source: Drug Bank)

Protein Binding

~10% (bound to plasma proteins) (source: Drug Bank)

Absorption

Rapidly and well absorbed from the gastrointestinal tract. (source: Drug Bank)

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. (source: Drug Bank)

Isomeric SMILES Code:

c1cnc(cn1)C(=O)N (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
XDH
  •   
  •   
  • PK
  • FA
  • GN
Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
FASN Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
cyclosporine Uncurated Annotation Pyrazinamide decreases the effect of cyclosporine (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Toxic liver disease
  •   
  • PD
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Tuberculosis
  • CO
  •   
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
xanthinuria
  •   
  •   
  • PK
  • FA
  • GN
Publications

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00339
ChEBI ID:
8656
KEGG Compound ID:
C01956
KEGG Drug ID:
D00144
PubChem Compound ID:
1046
PubChem Substance ID:
5057

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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