Record Information
Version1.0
Creation date2011-09-21 00:19:28 UTC
Update date2015-07-21 06:57:21 UTC
Primary IDFDB022776
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Hydroxypyrazinamide
DescriptionPyrazinamide Pyrazinamide is a drug used to treat tuberculosis in afflicted patients. The drug is largely bacteriostatic, but can be bacteriocidal on actively replicating tuberculosis bacteria. -- Wikipedia; Pyrazinamide is a generic drug and is available in a wide variety of presentations. Pyrazinamide tablets are usually 500mg and form the bulkiest part of the standard tuberculosis treatment regimen. Pyrazinamide tablets are so large that some patients find them impossible to swallow: pyrazinamide syrup is an option for these patients. -- Wikipedia; Pyrazinamide is also available as part of fixed dose combinations with other TB drugs such as isoniazid and rifampicin (Rifater is an example). -- Wikipedia; Pyrazinamide is well absorbed orally. It crosses inflamed meninges and is an essential part of the treatment of tuberculous meningitis. It is metabolised by the liver and the metabolic products are excreted by the kidneys. -- Wikipedia; Pyrazinamide is a pro-drug that stops the growth of Mycobacterium tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active at acidic pH. Pyrazinamidase converts pyrazinamide to the active form, pyrazinoic acid. Pyrazinoic acid inhibits the enzyme fatty acid synthetase I, which is required by the bacterium to synthesise fatty acids. Mutations of the pyrazinamidase gene (pncA) are responsible for pyrazinamide resistance in M. tuberculosis. -- Wikipedia [HMDB]
CAS Number13924-96-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.95 g/LALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.71 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H5N3O2
IUPAC name5-oxo-4,5-dihydropyrazine-2-carboxamide
InChI IdentifierInChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)
InChI KeyXENWQEOTDAQROM-UHFFFAOYSA-N
Isomeric SMILESNC(=O)C1=CNC(=O)C=N1
Average Molecular Weight139.1121
Monoisotopic Molecular Weight139.038176419
Classification
Description Belongs to the class of organic compounds known as pyrazinecarboxamides. Pyrazinecarboxamides are compounds containing a pyrazine ring which bears a carboxamide.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazinecarboxamides
Alternative Parents
Substituents
  • Pyrazinecarboxamide
  • 2-heteroaryl carboxamide
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Lactam
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5-Hydroxypyrazinamide, non-derivatized, GC-MS Spectrumsplash10-004v-9100000000-f3668d75358f611d3aeaSpectrum
GC-MS5-Hydroxypyrazinamide, non-derivatized, GC-MS Spectrumsplash10-004v-9100000000-f3668d75358f611d3aeaSpectrum
Predicted GC-MS5-Hydroxypyrazinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059j-9600000000-eed6c6621ac175ebc06fSpectrum
Predicted GC-MS5-Hydroxypyrazinamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-4a9bb4436286b18b224f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-3900000000-aa768b447648d6760f3d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kxr-9000000000-9af022e71bfdc81b06ad2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-b93be6c1c350e992bfab2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pc-5900000000-08d30dda33dea090dd132017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7932fdb1240ebaf3eef52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-f65eddb5dd85983512f22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-97da033a62736d0386e82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-9000000000-493cc79bdf78b0bf31122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-9500000000-a9e59e0dfcd47dd21c3d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pd-9800000000-682ec3f0b7fd06e498192021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90a8705015cfb3328f312021-09-22View Spectrum
NMRNot Available
ChemSpider ID133812
ChEMBL IDNot Available
KEGG Compound IDC01956
Pubchem Compound ID151823
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01978
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
ChickenExpected but not quantifiedNot AvailableHMDB
Columbidae (Dove, Pigeon)Expected but not quantifiedNot AvailableHMDB
DeerExpected but not quantifiedNot AvailableHMDB
Domestic goatExpected but not quantifiedNot AvailableHMDB
Domestic pigExpected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 29 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference