Compound: pyrazinamide
SMILES: O=C(N)c1nccnc1
InChIKey: IPEHBUMCGVEMRF-UHFFFAOYSA-N
Synonyms: pyrazinamide, pyrazinecarboxamide, 98-96-4, pyrazine-2-carboxamide, Zinamide, Aldinamide, Tebrazid, pyrazinoic acid amide, Aldinamid, Farmizina, Pirazimida, Pirazinamid, Unipyranamide, Eprazin, Novamid, Pyrafat, pyrazine carboxylamide, Pyrazineamide, Isopas, 2-Carbamylpyrazine, Pyrazinecarboxylic acid amide, Pirazinamida, Pyrazinamidum, Pyrazide, Rozide, Pirazinamide, Pyrazine carboxamide, pyramizade, MK 56, NCI-C01785, DTXSID9021215, MK-56, 2KNI5N06TI, NSC-14911, NSC14911, pyrazine-2-carboximidic acid, DTXCID801215, CHEBI:45285, 5-25-04-00178 (Beilstein Handbook Reference), alpha-pyrazinamide, pyrazinamide tablet, RefChem:6182, J04AK01, 202-717-6, Pirilene, 2-Pyrazinecarboxamide, D-50, PZA, MFCD00006132, NSC 14911, .alpha.-pyrazinamide, Tisamid, T 165, Pyrazinamide (Pyrazinoic acid amide), MLS000069730, Pezetamid, Piraldina, s1762, NCGC00015833-09, Pyrazinamdie, SMR000036662, Pirazinamide [DCIT], Pyrazinamidum [INN-Latin], Pirazinamida [INN-Spanish], Rifafour, D-50 (VAN), DRG 0124, CAS-98-96-4, CCRIS 545, Rifafour e-200, HSDB 3576, SR-01000076077, EINECS 202-717-6, UNII-2KNI5N06TI, BRN 0112306, pyrazinamida, Pyrizinamide, pyrazine amide, Pyrazinamide RS, Pyrazinamide CRS, Pyrazine-2-carboxylic acid amide, Pirazinecarboxamide, Pyrazinamide [USP:INN:BAN:JAN], Prestwick_811, Pyranzinoic acid amide, 2-pyrazine carboxamide, Spectrum_000902, Pyrazinamide (Standard), Opera_ID_735, pyrazine, 2-carbamoyl-, Prestwick0_000514, Prestwick1_000514, Prestwick2_000514, Prestwick3_000514, Spectrum2_001305, Spectrum3_001046, Spectrum4_001186, Spectrum5_001026, Lopac-P-7136, PYRAZINAMIDE [MI], PYRAZINAMIDE [INN], PYRAZINAMIDE [JAN], CHEMBL614, P 7136, PYRAZINAMIDE [HSDB], WLN: T6N DNJ BVZ, PYRAZINAMIDE [VANDF], Lopac0_001011, SCHEMBL24102, BSPBio_000467, BSPBio_002572, KBioGR_001851, KBioSS_001382, PYRAZINAMIDE [MART.], MLS002222347, BIDD:GT0228, DivK1c_000241, PYRAZINAMIDE [USP-RS], PYRAZINAMIDE [WHO-DD], PYRAZINAMIDE [WHO-IP], SCHEMBL733102, SCHEMBL956745, SPECTRUM1500518, SPBio_001369, SPBio_002388, BPBio1_000515, GTPL7287, orb1308657, orb3025148, SCHEMBL2438217, SCHEMBL4931800, SCHEMBL29408106, HMS500M03, HY-B0271R, KBio1_000241, KBio2_001382, KBio2_003950, KBio2_006518, KBio3_001792, Pyrazinamide (JP18/USP/INN), NINDS_000241, BDBM228814, HMS1569H09, HMS1920N08, HMS2092E09, HMS2096H09, HMS2235G17, HMS3259O04, HMS3263K03, HMS3371G09, HMS3655A10, HMS3713H09, HMS5080I03, KUC109577N, Pharmakon1600-01500518, PYRAZINAMIDE [ORANGE BOOK], PYRAZINAMIDE [EP MONOGRAPH], PYRAZINAMIDE [USP IMPURITY], ALBB-038645, HY-B0271, KSC-27-052E, WZB81781, PYRAZINAMIDE [USP MONOGRAPH], Tox21_110237, Tox21_202059, Tox21_302771, Tox21_501011, CCG-39243, EBC-03189, MSK000777, NSC757304, PYRAZINAMIDUM [WHO-IP LATIN], RIFATER COMPONENT PYRAZINAMIDE, SBB004276, STK801661, AKOS000120280, Tox21_110237_1, AP27270, DB00339, LP01011, NC00534, NSC-757304, Pyrazinecarboxamide, analytical standard, SDCCGSBI-0050984.P005, IDI1_000241, NCGC00015833-01, NCGC00015833-02, NCGC00015833-03, NCGC00015833-04, NCGC00015833-05, NCGC00015833-06, NCGC00015833-07, NCGC00015833-08, NCGC00015833-10, NCGC00015833-11, NCGC00015833-12, NCGC00015833-15, NCGC00015833-16, NCGC00015833-25, NCGC00090695-01, NCGC00090695-03, NCGC00090695-04, NCGC00090695-05, NCGC00090695-06, NCGC00090695-07, NCGC00256336-01, NCGC00259608-01, NCGC00261696-01, Pyrazinoic acid amide; pyrazinamide; PZA, CAS- 98-96-4, SY013550, TS-01626, SBI-0050984.P004, DB-002866, AB00052083, EU-0101011, NS00010008, P0633, ST45022155, SW196945-3, EN300-15621, C01956, D00144, D70481, AB00052083-16, AB00052083_17, AB00052083_18, AC-907/25014068, F068696, Q417571, SR-01000076077-1, SR-01000076077-4, SR-01000076077-6, BRD-K28667793-001-27-3, BRD-K28667793-001-28-1, Z33546644, Pyrazinamide, British Pharmacopoeia (BP) Reference Standard, Pyrazinamide, European Pharmacopoeia (EP) Reference Standard, Pyrazinamide, United States Pharmacopeia (USP) Reference Standard, InChI=1/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9, Pyrazinamide, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C5H5N3O
molecular_weight: 123.11 g/mol
exact_mass: 123.043261792 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 9
topological_polar_surface_area: 68.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
boiling_point: SUB (NTP, 1992)
melting_point: 376 to 379 °F (NTP, 1992)
solubility: Soluble (NTP, 1992)
Descriptions:
pubchem: Pyrazinecarboxamide is 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. It has a role as an antitubercular agent and a prodrug. It is a monocarboxylic acid amide, a member of pyrazines and a N-acylammonia.
chebi: 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.
chembl: PYRAZINAMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.
Pyrazinamide was first made in 1936, but did not come into wide use until 1972. It is on the World Health Organization's List of Essential Medicines. Pyrazinamide is available as a generic medication.