Pyrazinamide (CED0002135)

Record Information
Version1.0
Creation Date2016-05-22 03:30:32 UTC
Update Date2026-08-22 23:36:29 UTC
Accession NumberCHEM016404
Identification
Common NamePyrazinamide
ClassSmall Molecule
Description
Pyrazinamide (C5H5N3O) is an organic compound with an average molecular weight of 123.11 g/mol. Pyrazinamide belongs to the pyrazines, a subclass of diazines within the organic compounds. This substance is recorded as being found in or released from 36 different sources, including electrical and electronic equipment such as antennas, amplifiers, adjustable resistors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials, among 13 others. It is also found in building and construction materials, including stairs and ramps, ceilings, floors, roofs, and sunshades awnings or outside screens, as well as two additional sources. Other sources include household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and two others. Additionally, it is associated with food, food processing and cookware, specifically the preparation of malt, food preservation, and the processing of meats. Within healthcare, pharmaceuticals, and veterinary products, it is used in drugs for the treatment of tuberculosis. The recorded route of exposure is oral. Pyrazinamide acts on two recorded protein targets, serving as an inhibitor of enoyl-[acyl-carrier-protein] reductase [NADH] (inhA) and the probable fatty acid synthase Fas (fatty acid synthetase) (fas). Regarding its health effects, the compound is used as a treatment for tuberculosis (PMC10819319, PMC10963064, PMC11025081).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
2-CarbamylpyrazineChEBI
2-PyrazinecarboxamideChEBI
PyrazinamidaChEBI
PyrazinamidumChEBI
Pyrazine carboxamideChEBI
PYRAZINE-2-carboxamideChEBI
PyrazineamideChEBI
Pyrazinoic acid amideChEBI
Pyrazinoate amideGenerator
PirazimidaHMDB
PirazinamidHMDB
PyrazinamdieHMDB
Pyrazine carboxylamideHMDB
PyrazinecarboxamideHMDB
Pyrazinecarboxylic acid amideHMDB
PZAHMDB
TisamidHMDB
PyrazinamideChEBI
Chemical FormulaC5H5N3O
Average Molecular Mass123.113 g/mol
Monoisotopic Mass123.043 g/mol
CAS Registry Number98-96-4
IUPAC Namepyrazine-2-carboxamide
Traditional Namepyrazinamide
SMILESNC(=O)C1=NC=CN=C1
InChI IdentifierInChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChI KeyIPEHBUMCGVEMRF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Pyrazine
  • Heteroaromatic compound
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility93.7 g/LALOGPS
logP-0.71ALOGPS
logP-1.2ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)13.06ChemAxon
pKa (Strongest Basic)-0.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.87 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.45 m³·mol⁻¹ChemAxon
Polarizability11.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00ec-9400000000-d5dcdea97c58506b64c2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-1900000000-d29284f74cafc89d62adNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9200000000-f1f9853e24fa676ffa99Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001j-9000000000-7be5ab1fa895dc272521Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-9000000000-9c4235602fdfd2d2cdebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3009000000-ab4d0160c375af6d52eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-37eb3e998464288cbbf9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05ai-6900000000-45087b42af5c75ada6aeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zgi-9200000000-50b3f942e52f5925e0dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2900000000-f94eb5a23c26a4c9a87eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9800000000-ea7b102e875300f2f70bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-cd37c3a7e9f314fea54eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-1900000000-fc4d9556025fecfd087fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0059-9000000000-7864651f3a9fb2904c12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-9000000000-b69c290737e737bd3aebNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9300000000-f01174d71938c1ae0455Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-9200000000-8c30490f9e058d5b04c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-5d4ecfef90d7597892e8Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1327.0Log mg/kg[750:2400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
tuberculosisis_treatment_forNot AvailablePMC10819319 , PMC10963064 , PMC11025081
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
349Drugs for treatment of tuberculosisHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamaseQ44079Aeromonas hydrophilaPredicted (SEA)0.856341
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)1.08989
Click to view 3D structureD-aspartate oxidaseQ922Z0Mus musculusPredicted (SEA)0.700643
Click to view 3D structureD-aspartate oxidaseD3ZDM7Rattus norvegicusPredicted (SEA)0.700643
Click to view 3D structuretRNA (guanine-N(1)-)-methyltransferaseP0A873Escherichia coli (strain K12)Predicted (SEA)3.26967
Lysine-specific demethylase 4C structureClick to view 3D structureLysine-specific demethylase 4CQ9H3R0HumansPredicted (SEA)25.0674
Lysine-specific demethylase 4A structureClick to view 3D structureLysine-specific demethylase 4AO75164HumansPredicted (SEA)13.6236
Lysine-specific demethylase 4D structureClick to view 3D structureLysine-specific demethylase 4DQ6B0I6HumansPredicted (SEA)7.78492
Hydroxycarboxylic acid receptor 2 structureClick to view 3D structureHydroxycarboxylic acid receptor 2Q8TDS4HumansPredicted (SEA)2.95827
Lysine-specific demethylase 4E structureClick to view 3D structureLysine-specific demethylase 4EB2RXH2HumansPredicted (SEA)19.6959
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)1309.58
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)922.903
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)907.722
Click to view 3D structureMitogen-activated protein kinase kinase kinase kinase 2Q12851HumansPredicted (SEA)878.996
Death-associated protein kinase 3 structureClick to view 3D structureDeath-associated protein kinase 3O43293HumansPredicted (SEA)790.87
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)1515.34
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)970.624
Casein kinase I isoform alpha structureClick to view 3D structureCasein kinase I isoform alphaP48729HumansPredicted (SEA)876.738
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)1019.67
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)944.155
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)950.15
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1107.56
Cyclin-dependent kinase 8 structureClick to view 3D structureCyclin-dependent kinase 8P49336HumansPredicted (SEA)779.349
Lysine-specific demethylase 5B structureClick to view 3D structureLysine-specific demethylase 5BQ9UGL1HumansPredicted (SEA)22.1092
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)26.5466
Concentrations
Not Available
External Links
DrugBank IDDB00339
HMDB IDHMDB0014483
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyrazinamide
Chemspider ID1017
ChEBI ID45285
PubChem Compound ID1046
Kegg Compound IDC01956
YMDB IDYMDB00976
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Authors unspecified: Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4.
2. Authors unspecified: Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66.
3. Authors unspecified: A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6.
4. Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14977529
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18517115
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18604033