Pyrazinamide

Antimycobacterial — ANTIINFECTIVES FOR SYSTEMIC USE

Key facts

Pyrazinamide is an ofp drug in the Antimycobacterial class catalogued in DrugCentral. It was first approved by the FDA in 1971. DrugCentral lists 6 molecular targets, including CYP3A4, CA2 and CYP3A5. Recorded indications include Acute tuberculosis, Pulmonary tuberculosis and Tuberculosis of meninges.

• Approval status: ofp (first approved 1971 by the FDA).
• Drug class: Antimycobacterial.
• Molecular targets: CYP3A4, CA2, CYP3A5 and cmaA1 (6 listed in DrugCentral).
• Indications: Acute tuberculosis, Pulmonary tuberculosis and Tuberculosis of meninges.
• ATC code: J04AK01 (Other drugs for treatment of tuberculosis).
• Molecular formula: C5H5N3O; molecular weight 123.11 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (3)

• Acute tuberculosis
• Pulmonary tuberculosis
• Tuberculosis of meninges

Contraindications (18)

• Acute hepatic failure
• Acute hepatitis
• Acute nephropathy
• Alcoholism
• Anemia due to enzyme deficiency
• Chronic Hepatic Disease
• Diabetes mellitus
• Diabetic - poor control
• Diabetic peripheral neuropathy
• Disease of liver
• Gout
• Hepatic failure
• Jaundice
• Nutritional disorder
• Peripheral nerve disease
• Porphyria
• Prolonged-Severe Nausea and Vomiting
• Slow acetylator due to N-acetyltransferase enzyme variant

Mechanism & targets

• Established pharmacologic class: Antimycobacterial

Molecular targets (6)

Target	Gene	Action	Activity
Cytochrome P450 3A4	CYP3A4	unknown	IC50 6.89
Carbonic anhydrase 2	CA2	unknown	IC50 5.77
Cytochrome P450 3A5	CYP3A5	unknown	IC50 4.89
Cyclopropane mycolic acid synthase 1	cmaA1	unknown	—
Amidase; Nicotinamidase; Nicotinamidase/pyrazinamidase; Pyrazinamidase; Pyrazinamidase/nicotinamidase; Pyrazinamidase/nicotinamidase PncA	pncA	unknown	—
3-oxoacyl-ACP synthase; Fatty acid synthase Fas; Probable fatty acid synthase Fas (Fatty acid synthetase)	fas	inhibitor	—

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1971-06-03	FDA	—	DAVA PHARMS INC

ATC classification

ATC code	Therapeutic hierarchy
J04AK01	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Other drugs for treatment of tuberculosis
J04AM05	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis
J04AM06	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis
J04AM09	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis
J04AM10	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis
J04AM11	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis
J04AM12	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOBACTERIALS › DRUGS FOR TREATMENT OF TUBERCULOSIS › Combinations of drugs for treatment of tuberculosis

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Paradoxical drug reaction	2201.6
Drug reaction with eosinophilia and systemic symptoms	1848.5
Drug-induced liver injury	1346.7
Immune reconstitution inflammatory syndrome	1109.2
Immune reconstitution inflammatory syndrome associated tuberculosis	865.4
Drug resistance	793.4
Hepatotoxicity	724.6
Acute hepatic failure	564.9
Tuberculoma of central nervous system	473.4
Drug interaction	447.1
Jaundice	435.8
Tuberculosis	425.3

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Pyrazinamide is on its molecule page.

• Molecular formula: C₅H₅N₃O
• Molecular weight: 123.11 g/mol
• CAS number: 98-96-4
• InChIKey: IPEHBUMCGVEMRF-UHFFFAOYSA-N
• PubChem CID: 1046

NC(=O)C1=NC=CN=C1

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Pyrazinamide used for?

DrugCentral lists the following indications for Pyrazinamide: Acute tuberculosis, Pulmonary tuberculosis and Tuberculosis of meninges.

How does Pyrazinamide work?

Its molecular targets in DrugCentral include CYP3A4, CA2, CYP3A5 and cmaA1.

When was Pyrazinamide first approved?

Pyrazinamide was first approved by the FDA in 1971.

What drug class does Pyrazinamide belong to?

Pyrazinamide is in the Antimycobacterial class.

What is the chemical formula of Pyrazinamide?

Pyrazinamide has the molecular formula C5H5N3O and a molecular weight of 123.11 g/mol.

Sources

• DrugCentral drug card 2328 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL614 — compound record and bioactivity
• PubChem CID 1046 — chemical identifiers
• DrugBank DB00339 — drug record
• FDA UNII 2KNI5N06TI — substance identity
• DailyMed: FDA labels for Pyrazinamide — current prescribing information (label search)
• UniProt P08684 (CYP3A4) — target protein
• UniProt P00918 (CA2) — target protein
• UniProt P20815 (CYP3A5) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.