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

General Information of Drug (ID: DR2212)
Drug Name
Nitroimidazole
Synonyms Nitroimidazole; Nitroimidazole compound; 2-Nitroimidazole; Nitroimidazole compounds (infection)
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 113.08 Topological Polar Surface Area 74.5
Heavy Atom Count 8 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
10701
ChEBI ID
CHEBI:67135
CAS Number
527-73-1
TTD Drug ID
D0QY4L
Formula
C3H3N3O2
Canonical SMILES
C1=CN=C(N1)[N+](=O)[O-]
InChI
1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
InChIKey
YZEUHQHUFTYLPH-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
IM2O DM004001 N. A. Hydrolysis - Hydrolytic denitration 1 [2]
Nitroimidazole Metabolite M6 DM004000 N. A. Reduction - Reduction 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012895 Nitroimidazole Nitroimidazole Metabolite M6 Reduction - Reduction hyaA [6]
MR012896 Nitroimidazole IM2O Hydrolysis - Hydrolytic denitration nnhA [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
2-nitroimidazole nitrohydrolase (nnhA) DMEN191 Mycobacterium sp.
NNHA_MYCS0
3.5.99.9
[2]
Hydrogenase-1 small chain (hyaA) DMEN190 Escherichia coli
MBHS_ECOLI
1.12.99.6
[3]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1971 Salmonella enterica
NFSA_SALTY
1.5.1.38
[4]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1617 Salmonella enterica
NFSB_SALTY
1.5.1.34
[4]
Retro-nitroreductase (rNR) DME1584 Enterobacter cloacae
A0A0H3CM55_ENTCC
1.5.1.34
[5]
References
1 PubChem 2019 update: improved access to chemical data. Nucleic Acids Res. 2019 Jan 8; 47(D1):D1102-1109. (PubChem CID: 10701)
2 Catabolic pathway for 2-nitroimidazole involves a novel nitrohydrolase that also confers drug resistance
3 Reduction of 2-, 4- and 5-nitroimidazole drugs by hydrogenase 1 in Clostridium pasteurianum
4 Delamanid is not metabolized by Salmonella or human nitroreductases: a possible mechanism for the lack of mutagenicity. Regul Toxicol Pharmacol. 2017 Mar;84:1-8.
5 Retro-nitroreductase, a putative evolutionary precursor to Enterobacter cloacae strain 96-3 nitroreductase. Antioxid Redox Signal. 2001 Oct;3(5):747-55.
6 U. S. FDA Label -Nitroimidazole

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