Structure via PubChem · Public domain (PubChem)
pyrazinamide
Sign in to saveAlso known as Zinamide®, PZA, Pyrazine carboxamide, Pyrazineamide, Pirazinamida, Pyrazinamidum, Pirazinamide
Pyrazinamide is a medication used to treat tuberculosis. For active tuberculosis, it is often used with rifampicin, isoniazid, and either streptomycin or ethambutol. It is not generally recommended for the treatment of latent tuberculosis. It is taken by mouth.
Chemical data
- Formula
- C5H5N3O
- Molecular weight
- 123.11 g/mol
- IUPAC name
- pyrazine-2-carboxamide
- SMILES
- C1=CN=C(C=N1)C(=O)N
- InChIKey
- IPEHBUMCGVEMRF-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 68.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
6,571 papers- Pyrazinamide.Tuberculosis (Edinburgh, Scotland) · 2008
- Pyrazinamide Safety, Efficacy, and Dosing for Treating Drug-Susceptible Pulmonary Tuberculosis: A Phase 3, Randomized Controlled Clinical Trial.American journal of respiratory and critical care medicine · 2024
- Pyrazinamide resistance in rifampicin discordant tuberculosis.PloS one · 2022
- Anti-Tubercular Activity of Pyrazinamide Conjugates: Synthesis and Structure-Activity Relationship Studies.Mini reviews in medicinal chemistry · 2023
- Pyrazinamide may possess cardioprotective properties.The Journal of antibiotics · 2019
via PubMed
Wikidata facts
- Mass
- 123.043
Show 8 more facts
- chemical formula
- C₅H₅N₃O
- melting point
- 190
- pKa
- 0.5
- canonical SMILES
- C1=CN=C(C=N1)C(=O)N
- World Health Organisation international non-proprietary name
- pyrazinamide
- defined daily dose
- 1.5
- Commons category
- Pyrazinamide
- MCN code
- 2933.99.11
Sources (6)
via Wikidata · CC0
~8 min read
Article
9 sectionsContents
- Medical uses
- Adverse effects
- Pharmacokinetics
- Mechanism of action
- Resistance
- Abbreviations
- Presentation
- History
- References
Pyrazinamide is a medication used to treat tuberculosis. For active tuberculosis, it is often used with rifampicin, isoniazid, and either streptomycin or ethambutol. It is not generally recommended for the treatment of latent tuberculosis. It is taken by mouth.
Common side effects include nausea, loss of appetite, muscle and joint pains, and rash. More serious side effects include gout, liver toxicity, and sensitivity to sunlight. It is not recommended in those with significant liver disease or porphyria. It is unclear if use during pregnancy is safe but it is likely okay during breastfeeding. Pyrazinamide is in the antimycobacterial class of medications. How it works is not entirely clear.