Pyrazinamide
drugOn this page
Also known as .alpha.-pyrazinamideAldinamidAldinamideD-50EprazinFarmizinaIsopasMK-56NovamidNSC-14911PirazimidaPirazinamidPirazinamidaPirilenePyrafatPyramizadePyrazidePyrazinamide component of rifaterPyrazinamidum
Summary
Pyrazinamide (CHEMBL614) is an approved small-molecule antitubercular agent (ATC J04AK01); indicated across 8 conditions including pulmonary tuberculosis and tuberculosis.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J04AK01
- Indications: 8 conditions
- Clinical trials: 70
- Chemistry: 123.11 Da · C5H5N3O
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL614 |
| Name | Pyrazinamide |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 1046 |
| ChEBI | CHEBI:45285 |
| ATC | J04AK01 |
| Molecular formula | C5H5N3O |
| Molecular weight | 123.11 |
| InChIKey | IPEHBUMCGVEMRF-UHFFFAOYSA-N |
SMILES: C1=CN=C(C=N1)C(=O)N
IUPAC name: pyrazine-2-carboxamide
ChEBI definition: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.
Pharmacological roles (ChEBI): antitubercular agent, prodrug.
Also known as: .alpha.-pyrazinamide, Aldinamid, Aldinamide, D-50, Eprazin, Farmizina, Isopas, MK-56, Novamid, NSC-14911, Pirazimida, Pirazinamid
Parent form; salt/anhydrous children: CHEMBL1091434
Patent coverage: 7,723 distinct patent families (25,198 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 25,175 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Thyrotropin receptor, Alpha-1A adrenergic receptor, Adenosine receptor A3, Melanocortin receptor 4, Melanocortin receptor 3.
Bioactivity
ChEMBL activities: 3 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| TSHR | 7.7 | Potency | 20 | nM | CHEMBL_ACT_3915378 |
| TSHR | 7.7 | Potency | 20 | nM | CHEMBL_ACT_4719071 |
| ADORA3 | 5.41 | AC50 | 3856 | nM | CHEMBL_ACT_25133893 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
8 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| pulmonary tuberculosis | 4 | MONDO:0006052 | EFO:1000049 |
| tuberculosis | 4 | MONDO:0018076 | MONDO:0018076 |
| multidrug-resistant tuberculosis | 3 | MONDO:0005861 | EFO:0007381 |
| meningitis | 3 | MONDO:0021108 | MONDO:0021108 |
| AIDS | 2 | MONDO:0012268 | EFO:0000765 |
| HIV infectious disease | 1 | MONDO:0005109 | EFO:0000764 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 70.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 26 |
| PHASE3 | 17 |
| Not specified | 11 |
| PHASE4 | 8 |
| PHASE2/PHASE3 | 4 |
| PHASE1 | 4 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00402454 | PHASE4 | COMPLETED | Evaluation of Three Regimens of Chemoprophylaxis for Tuberculosis in Patients co-Infected by HIV and Mycobacterium Tuberculosis |
| NCT01380080 | PHASE4 | COMPLETED | REMEMBER: Reducing Early Mortality & Morbidity by Empiric Tuberculosis (TB) Treatment |
| NCT01395654 | PHASE4 | UNKNOWN | Reintroduction Regimens After Hepatitis During Anti-tuberculosis Treatment |
| NCT01782950 | PHASE4 | UNKNOWN | Evaluation of the Pharmacokinetics of Antituberculosis Drugs and Tuberculosis Treatment Outcomes |
| NCT02057796 | PHASE4 | COMPLETED | Systematic Empirical vs. Test-guided Anti-TB Treatment Impact in Severely Immunosuppressed HIV-infected Adults Initiating ART With CD4 Cell Counts <100/mm3 |
| NCT02477852 | PHASE4 | UNKNOWN | The Optimal Duration of Preoperative Anti-tuberculosis Treatment of Spinal Tuberculosis |
| NCT02901288 | PHASE4 | UNKNOWN | Shortened Regimens for Drug-susceptible Pulmonary Tuberculosis |
| NCT05306223 | PHASE4 | UNKNOWN | A Study of an Oral Short-course Regimen Including Bedaquiline for the Treatment of Participants With Multidrug-resistant Tuberculosis in China |
| NCT04485156 | PHASE3 | NOT_YET_RECRUITING | Treatment Shortening of Drug-Sensitive Pulmonary Tuberculosis Using High Dose Rifampicin (Hi-DoRi-3) |
| NCT05454345 | PHASE3 | NOT_YET_RECRUITING | Sitafloxacin-containing Regimens for Shortening Tuberculosis Treatment |
| NCT05766267 | PHASE2/PHASE3 | ACTIVE_NOT_RECRUITING | Short-course Regimens for the Treatment of Pulmonary Tuberculosis |
| NCT05917340 | PHASE3 | NOT_YET_RECRUITING | Intensified Short Course Regimen for TBM in Adults |
| NCT06081361 | PHASE3 | ACTIVE_NOT_RECRUITING | Innovating Shorter, All- Oral, Precised, Individualized Treatment Regimen for Rifampicin Resistant Tuberculosis：Contezolid, Delamanid and Bedaquiline Cohort |
| NCT06253715 | PHASE3 | RECRUITING | Shortened Regimen for Drug-susceptible TB in Children |
| NCT00001033 | PHASE3 | COMPLETED | The Treatment of Tuberculosis in HIV-Infected Patients |
| NCT00130247 | PHASE3 | COMPLETED | Tuberculosis Treatment Shortening Trial |
| NCT00317330 | PHASE3 | COMPLETED | A Randomized Trial of DOTS Versus Enhanced DOTS for Community Control of Tuberculosis |
| NCT00698334 | PHASE3 | COMPLETED | Efficacy of Thrice Weekly Directly Observed Treatment, Short-course (DOTS) in HIV-associated Tuberculosis |
| NCT00933790 | PHASE3 | COMPLETED | Comparing Daily vs Intermittent Regimen of ATT in HIV With Pulmonary Tuberculosis |
| NCT02342886 | PHASE3 | COMPLETED | Shortening Treatment by Advancing Novel Drugs |
| NCT02409290 | PHASE3 | COMPLETED | The Evaluation of a Standard Treatment Regimen of Anti-tuberculosis Drugs for Patients With MDR-TB |
| NCT02454205 | PHASE2/PHASE3 | COMPLETED | An Open-label RCT to Evaluate a New Treatment Regimen for Patients With Multi-drug Resistant Tuberculosis |
| NCT02563327 | PHASE3 | COMPLETED | Pharmacokinetic and Pharmacodynamic Study of High-Dose Rifapentine and Moxifloxacin for Treatment of Tuberculosis |
| NCT02581527 | PHASE3 | COMPLETED | A Randomised Trial to Evaluate Toxicity and Efficacy of 1200mg and 1800mg Rifampicin for Pulmonary Tuberculosis |
| NCT02754765 | PHASE3 | COMPLETED | Evaluating Newly Approved Drugs for Multidrug-resistant TB |
| NCT02975570 | PHASE3 | WITHDRAWN | Efficacy and Tolerability of Delamanid, Linezolid, Pyrazinamide and Levofloxacin |
| NCT03338621 | PHASE2/PHASE3 | COMPLETED | Trial to Evaluate the Efficacy, Safety and Tolerability of BPaMZ in Drug-Sensitive (DS-TB) Adult Patients and Drug-Resistant (DR-TB) Adult Patients |
| NCT03474198 | PHASE2/PHASE3 | COMPLETED | Two-month Regimens Using Novel Combinations to Augment Treatment Effectiveness for Drug-sensitive Tuberculosis |
| NCT04062201 | PHASE3 | COMPLETED | Building Evidence for Advancing New Treatment for Rifampicin Resistant Tuberculosis (RR-TB) Comparing a Short Course of Treatment (Containing Bedaquiline, Delamanid and Linezolid) With the Current South African Standard of Care |
| NCT05383742 | PHASE2 | RECRUITING | Trial of a Six-Month Regimen of High-Dose Rifampicin, High-Dose Isoniazid, Linezolid, and Pyrazinamide Versus a Standard Nine-Month Regimen for the Treatment of Adults and Adolescents With Tuberculous Meningitis |
| NCT05556746 | PHASE2 | ACTIVE_NOT_RECRUITING | Ultra-Short Course Bedaquiline, Clofazimine, Pyrazinamide and Delamanid Versus Standard Therapy for Drug-Susceptible TB |
| NCT05807399 | PHASE2 | RECRUITING | PanACEA - STEP2C -01 |
| NCT06192160 | PHASE2 | RECRUITING | Trial of Novel Regimens for the Treatment of Pulmonary Tuberculosis |
| NCT06917495 | PHASE2 | NOT_YET_RECRUITING | Short-Course Anti-tuberculosis Regimens for Mild Spinal Tuberculosis |
| NCT07073638 | PHASE2 | RECRUITING | Phase 2 Trial to Evaluate the Safety and Tolerability and Early Bactericidal Activity of RESP30TB in Tuberculosis |
| NCT07129629 | PHASE2 | NOT_YET_RECRUITING | Short-Course Regimen With Bedaquiline, Moxifloxacin and Pyrazinamide for Early Bactericidal Activity in Drug-Susceptible Tuberculosis |
| NCT07467252 | PHASE2 | NOT_YET_RECRUITING | AIPH-TB: AI-Optimised Pyrazinamide-Hydroxychloroquine vs Standard RIPE for Drug-Sensitive Pulmonary Tuberculosis - A Phase II RCT |
| NCT07595042 | PHASE2 | NOT_YET_RECRUITING | A Trial of Stratified Patient-Centered Treatment Regimens for Active TB (SPECTRA-TB) |
| NCT00728507 | PHASE2 | TERMINATED | Rifapentine Plus Moxifloxacin for Treatment of Pulmonary Tuberculosis |
| NCT01215851 | PHASE2 | COMPLETED | Evaluation of Early Bactericidal Activity in Pulmonary Tuberculosis With(J-M-Pa-Z) (NC-001) |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 9 clinical and 130 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).