Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1372)
Drug Name
Pyrazinamide
Prodrug Info Pyrazinamide is the prodrug of PZA
Synonyms
Pezetamid; Piraldina; Pirazimida; Pirazinamid; Pirazinamida; Pirazinamide; Prazina; Pyrafat; Pyramide; Pyrazide; Pyrazinamdie; Pyrazinamidum; Pyrazine carboxamide; Pyrazineamide; Pyrazinecarboxylic acid amide; Rozide; Tebrazid; Aldinamid; Aldinamide; Braccopiral; Corsazinmid; Dipimide; Eprazin; Farmizina; Isopas; Lynamide; Novamid; Tebrazio; Tisamid; Unipyranamide; Zinamide; Zinastat; pyrazinamide; pyrazine carboxylamide; pyrazine-2-carboxamide; pyrazinecarboxamide; pyrazinoic acid amide; 2-Carbamylpyrazine; 2-Pyrazinecarboxamide; 98-96-4
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 123.11 Topological Polar Surface Area 68.9
Heavy Atom Count 9 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
1046
PubChem SID
3115 ; 5057 ; 78938 ; 602930 ; 866420 ; 3135875 ; 7437580 ; 7847212 ; 7980439 ; 8002616 ; 8139959 ; 8149510 ; 10321757 ; 10539072 ; 11111657 ; 11111658 ; 11335416 ; 11360655 ; 11363796 ; 11366358 ; 11368920 ; 11371892 ; 11374989 ; 11377082 ; 11461627 ; 11466542 ; 11467662 ; 11485105 ; 11486124 ; 11489121 ; 11490861 ; 11493000 ; 11494716 ; 15119868 ; 16957225 ; 17389747 ; 17405569 ; 24278648 ; 24439399 ; 24887930 ; 25623302 ; 26611902 ; 26679227 ; 26697102 ; 26747228 ; 26747229 ; 26752748 ; 39214717 ; 46507478 ; 47810638
ChEBI ID
ChEBI:45285
CAS Number
98-96-4
TTD Drug ID
D0XF8W
Formula
C5H5N3O
Canonical SMILES
C1=CN=C(C=N1)C(=O)N
InChI
1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChIKey
IPEHBUMCGVEMRF-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5-hydroxypyrazinamide DM003025
151823
Oxidation - Oxidation 1 [2] , [5] , [6]
PZA DM000472
1047
Oxidation - Oxidation 1 [2] , [5] , [6]
5-hydroxypyrazinoic acid DM003024
161825
Unclear 2 [2] , [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002201 Pyrazinamide Pyrazinoic acid Oxidation - Oxidation pncA [2], [5], [6]
MR002202 Pyrazinamide 5-hydroxypyrazinamide Oxidation - Oxidation AOX1 ... [2], [5], [6]
MR002200 5-hydroxypyrazinamide 5-hydroxypyrazinoic acid Unclear pncA [2], [5], [6]
MR002199 Pyrazinoic acid 5-hydroxypyrazinoic acid Unclear XDH [2], [5], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Nicotinamidase (pncA) DME1076 Acinetobacter baumannii
B0VA03_ACIBY
3.5.1.19
[4]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[5]
References
1 Pyrazinamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Factors Affecting the Pharmacokinetics of Pyrazinamide and Its Metabolites in Patients Coinfected with HIV and Implications for Individualized Dosing Antimicrob Agents Chemother. 2021 Jun 17;65(7):e0004621. doi: 10.1128/AAC.00046-21.
3 The metabolism of pyrazoloacridine (NSC 366140) by cytochromes p450 and flavin monooxygenase in human liver microsomes. Clin Cancer Res. 2004 Feb 15;10(4):1471-80.
4 Specificity and mechanism of Acinetobacter baumanii nicotinamidase: implications for activation of the front-line tuberculosis drug pyrazinamide. Angew Chem Int Ed Engl. 2009;48(48):9176-9.
5 Metabolism and Hepatotoxicity of Pyrazinamide, an Antituberculosis Drug Drug Metab Dispos. 2021 Aug;49(8):679-682. doi: 10.1124/dmd.121.000389.
6 Determination of pyrazinamide and its main metabolites in rat urine by high-performance liquid chromatography J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):365-72. doi: 10.1016/s0378-4347(97)00175-8.

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