MiMeDB: Showing metabocard for Pyrazinecarboxamide (MMDBc0033197)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:38:41 UTC

Update Date

2022-08-31 22:29:43 UTC

Metabolite ID

MMDBc0033197

Metabolite Identification

Common Name

Pyrazinecarboxamide

Description

Pyrazinecarboxamide, also known as pyrazinamide, is only found in individuals that have used or taken this drug. It is a pyrazine that is used therapeutically as an antitubercular agent. Pyrazinecarboxamide is an important sterilizing prodrug that shortens tuberculosis (TB) therapy. However, the mechanism of action of pyrazinecarboxamide is poorly understood because of its unusual properties. In literature it has been written that the pyrazinoic acid (POA), the active moiety of pyrazinecarboxamide, 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 pyrazinecarboxamide to POA, and the vitro susceptibility of a given strain of the organism appears to correspond to its pyrazinamidase activity. Experimental evidence suggests that pyrazinecarboxamide 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 pyrazinecarboxamide and its analogs inhibit the activity of purified FAS I.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₅H₅N₃O

Average Mass

123.1127

Monoisotopic Mass

123.043261797

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

98-96-4

SMILES

Not Available

InChI Identifier

InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)

InChI Key

IPEHBUMCGVEMRF-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191797	Aldehyde oxidase	Unknown	Q06278	Homo_sapiens
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo_sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo_sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown
Bacteria	Proteobacteria	1
Bacteria	Actinobacteria	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

Not Available

General References

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 ]
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. doi: 10.1016/0041-3879(83)90011-9. [PubMed:6356538 ]
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 ]
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. doi: 10.1164/rccm.200206-626OC. Epub 2003 Jan 31. [PubMed:12569078 ]

Showing metabocard for Pyrazinecarboxamide (MMDBc0033197)

MOL for #<Metabolite:0x0000560be2091e08>

3D MOL for #<Metabolite:0x0000560be2091e08>

3D SDF for #<Metabolite:0x0000560be2091e08>

3D-SDF for #<Metabolite:0x0000560be2091e08>

PDB for #<Metabolite:0x0000560be2091e08>

3D PDB for #<Metabolite:0x0000560be2091e08>

SMILES for #<Metabolite:0x0000560be2091e08>

INCHI for #<Metabolite:0x0000560be2091e08>

Structure for #<Metabolite:0x0000560be2091e08>

3D Structure for #<Metabolite:0x0000560be2091e08>