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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:10 UTC
HMDB IDHMDB0014483
Secondary Accession Numbers
  • HMDB14483
Metabolite Identification
Common NamePyrazinamide
DescriptionPyrazinamide is only found in individuals that have used or taken this drug. It is a pyrazine that is used therapeutically as an antitubercular agent.Pyrazinamide is an important sterilizing prodrug that shortens tuberculosis (TB) therapy. However, the mechanism of action of pyrazinamide is poorly understood because of its unusual properties. In literature it has been written that the pyrazinoic acid (POA), the active moiety of pyrazinamide, disrupted membrane energetics and inhibited membrane transport function at acid pH in Mycobacterium tuberculosis. The antimycobacterial activity appears to partly depend on conversion of the drug to POA. Susceptible strains of M. tuberculosis produce pyrazinamidase, an enzyme that deaminates pyrazinamide to POA, and the vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. Experimental evidence suggests that pyrazinamide diffuses into M. tuberculosis in a passive manner, is converted into POA by pyrazinamidase, and because of an inefficient efflux system, accumulates in huge amounts in the bacterial cytoplasm. The accumulation of POA lowers the intracellular pH to a suboptimal level that is likely to inactivate a vital target enzyme such as fatty acid synthase. Recent studies (2007) demonstrated that pyrazinamide and its analogs inhibit the activity of purified FAS I.
Structure
Data?1676999890
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 Weight123.1127
Monoisotopic Molecular Weight123.043261797
IUPAC Namepyrazine-2-carboxamide
Traditional Namepyrazinamide
CAS Registry Number98-96-4
SMILES
NC(=O)C1=NC=CN=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility93.7 g/LNot Available
LogP-1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.58631661259
DarkChem[M-H]-118.06631661259
DeepCCS[M+H]+124.96830932474
DeepCCS[M-H]-121.6230932474
DeepCCS[M-2H]-158.64730932474
DeepCCS[M+Na]+133.74830932474
AllCCS[M+H]+126.532859911
AllCCS[M+H-H2O]+121.732859911
AllCCS[M+NH4]+130.932859911
AllCCS[M+Na]+132.232859911
AllCCS[M-H]-120.932859911
AllCCS[M+Na-2H]-123.032859911
AllCCS[M+HCOO]-125.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrazinamideNC(=O)C1=NC=CN=C11703.1Standard polar33892256
PyrazinamideNC(=O)C1=NC=CN=C11265.0Standard non polar33892256
PyrazinamideNC(=O)C1=NC=CN=C11221.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrazinamide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CN=CC=N11447.2Semi standard non polar33892256
Pyrazinamide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CN=CC=N11460.6Standard non polar33892256
Pyrazinamide,1TMS,isomer #1C[Si](C)(C)NC(=O)C1=CN=CC=N12204.0Standard polar33892256
Pyrazinamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C1496.8Semi standard non polar33892256
Pyrazinamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C1559.9Standard non polar33892256
Pyrazinamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C2072.3Standard polar33892256
Pyrazinamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=N11653.3Semi standard non polar33892256
Pyrazinamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=N11614.5Standard non polar33892256
Pyrazinamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C1=CN=CC=N12392.4Standard polar33892256
Pyrazinamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C1908.5Semi standard non polar33892256
Pyrazinamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C1925.5Standard non polar33892256
Pyrazinamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C2258.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrazinamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ec-9400000000-d5dcdea97c58506b64c22016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrazinamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazinamide LC-ESI-QQ , positive-QTOFsplash10-0ab9-1900000000-d29284f74cafc89d62ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazinamide LC-ESI-QQ , positive-QTOFsplash10-001i-9200000000-f1f9853e24fa676ffa992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazinamide LC-ESI-QQ , positive-QTOFsplash10-001j-9000000000-7be5ab1fa895dc2725212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazinamide LC-ESI-QQ , positive-QTOFsplash10-000t-9000000000-9c4235602fdfd2d2cdeb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazinamide LC-ESI-QQ , positive-QTOFsplash10-014i-3009000000-ab4d0160c375af6d52ee2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 10V, Positive-QTOFsplash10-00di-0900000000-37eb3e998464288cbbf92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 20V, Positive-QTOFsplash10-05ai-6900000000-45087b42af5c75ada6ae2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 40V, Positive-QTOFsplash10-0zgi-9200000000-50b3f942e52f5925e0db2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 10V, Negative-QTOFsplash10-00di-2900000000-f94eb5a23c26a4c9a87e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 20V, Negative-QTOFsplash10-00dl-9800000000-ea7b102e875300f2f70b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 40V, Negative-QTOFsplash10-0006-9000000000-cd37c3a7e9f314fea54e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 10V, Positive-QTOFsplash10-05fr-1900000000-fc4d9556025fecfd087f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 20V, Positive-QTOFsplash10-0059-9000000000-7864651f3a9fb2904c122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 40V, Positive-QTOFsplash10-0udi-9000000000-b69c290737e737bd3aeb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 10V, Negative-QTOFsplash10-004i-9300000000-f01174d71938c1ae04552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 20V, Negative-QTOFsplash10-002f-9200000000-8c30490f9e058d5b04c82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazinamide 40V, Negative-QTOFsplash10-0006-9000000000-5d4ecfef90d7597892e82021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00339 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00339 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00339
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1017
KEGG Compound IDC01956
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrazinamide
METLIN IDNot Available
PubChem Compound1046
PDB IDNot Available
ChEBI ID45285
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:6109855 ]
  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. [PubMed:6356538 ]
  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. [PubMed:6386028 ]
  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. [PubMed:12569078 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
References
  1. Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [PubMed:8216357 ]
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [PubMed:8216357 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]