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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2023-02-21 17:16:01 UTC
HMDB IDHMDB0001978
Secondary Accession Numbers
  • HMDB01978
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
5-oxo-4,5-Dihydropyrazine-2-carboximidateGenerator, HMDB
5-HydroxypyrazinamideMeSH
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 KeyXENWQEOTDAQROM-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022776
KNApSAcK IDNot Available
Chemspider ID133812
KEGG Compound IDC01956
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6413
PubChem Compound151823
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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. [PubMed: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. [PubMed:3663245 ]