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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2016-02-11 01:05:11 UTC
HMDB IDHMDB01978
Secondary Accession NumbersNone
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
2-carboxamido-5-HydroxypyrazineHMDB
5-Hydroxy-(8ci)-pyrazinecarboxamideHMDB
5-HydroxypyrazinecarboxamideHMDB
Chemical FormulaC5H5N3O2
Average Molecular Weight139.1121
Monoisotopic Molecular Weight139.038176419
IUPAC Name5-oxo-4,5-dihydropyrazine-2-carboxamide
Traditional Name5-oxo-4H-pyrazine-2-carboxamide
CAS Registry Number13924-96-4
SMILES
NC(=O)C1=CNC(=O)C=N1
InChI Identifier
InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)
InChI KeyInChIKey=XENWQEOTDAQROM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrazinecarboxamides. These are compounds containing a pyrazine ring which bears a carboxamide.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazinecarboxamides
Alternative Parents
Substituents
  • Pyrazinecarboxamide
  • Heteroaromatic compound
  • Vinylogous amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.95 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.71 m3·mol-1ChemAxon
Polarizability12.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00415
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022776
KNApSAcK IDNot Available
Chemspider ID133812
KEGG Compound IDC01956
BioCyc IDPYRAZINAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01978
Metagene LinkHMDB01978
METLIN ID6413
PubChem Compound151823
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMoriwaki 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. Biochemical pharmacology (1993), 46(6), 975-81.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lacroix C, Poncet P, Laine G, Guyonnaud C, Ray M, Menager S, Lafont O: [Microdetermination of pyrazinamide and its metabolites (pyrazinoic acid, 5-hydroxypyrazinoic acid, 5-hydroxypyrazinamide and pyrazinuric acid) in plasma and urine with liquid chromatography] J Chromatogr. 1987 Nov 27;422:217-25. [3437007 ]

Enzymes

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. Yamamoto T, Moriwaki Y, Takahashi S, Hada T, Higashino K: In vitro conversion of pyrazinamide into 5-hydroxypyrazinamide and that of pyrazinoic acid into 5-hydroxypyrazinoic acid by xanthine oxidase from human liver. Biochem Pharmacol. 1987 Oct 1;36(19):3317-8. [3663245 ]