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

General Information of Drug (ID: DR2185)
Drug Name
Misonidazole
Synonyms
Misonidazol [INN-Spanish]; Misonidazole; Misonidazolum [INN-Latin]; Ro 7-0582; SR 1354; SRI 1354; 1-(2'-hydroxy-3'-methoxypropyl)-2-nitroimidazole; 1-(2-Hydroxy-3-methoxypropyl)-2-nitroimidazole; 1-(2-NITRO-1-IMIDAZOLYL)-3-METHOXY-2-PROPANOL; 1-methoxy-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol; 1-methoxy-3-(2-nitroimidazol-1-yl)propan-2-ol; 13551-87-6; BRN 0613655; CCRIS 1160; EINECS 236-931-6; MLS003115361; NSC-261,037; NSC-261037; NSC261037; alpha-(Methoxymethyl)-2-nitro-1H-imidazole-1-ethanol
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 201.18 Topological Polar Surface Area 93.1
Heavy Atom Count 14 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
26105
CAS Number
13551-87-6
Formula
C7H11N3O4
Canonical SMILES
COCC(CN1C=CN=C1[N+](=O)[O-])O
InChI
1S/C7H11N3O4/c1-14-5-6(11)4-9-3-2-8-7(9)10(12)13/h2-3,6,11H,4-5H2,1H3
InChIKey
OBBCSXFCDPPXOL-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
Desmethylmisonidazole DM003921
26106
Unclear 1 [4]
Nitroso DM003916 N. A. Reduction - Reduction 1 [5]
[1-(2-aminoimidazol-1-yl)-3-methoxypropan-2-ol] (AIM) DM003919
127524
Unclear 1 [6]
(2-hydroxy-3-methoxypropyl)-guanidine (G) DM003920
13805825
Hydrolysis - Hydrolyzation 2 [6]
N-hydroxylamine DM003917 N. A. Reduction - Reduction 2 [3]
Urea DM001344
1176
Hydrolysis - Hydrolyzation 2 [6]
Amine DM003918 N. A. Reduction - Reduction 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004278 Misonidazole Nitroso Reduction - Reduction Unclear [5]
MR004281 Misonidazole [1-(2-aminoimidazol-1-yl)-3-methoxypropan-2-ol] (AIM) Unclear Unclear [6]
MR004284 Misonidazole Desmethylmisonidazole Unclear Unclear [4]
MR004279 Nitroso N-hydroxylamine Reduction - Reduction XDH [3]
MR004282 [1-(2-aminoimidazol-1-yl)-3-methoxypropan-2-ol] (AIM) Urea Hydrolysis - Hydrolyzation Unclear [6]
MR004283 [1-(2-aminoimidazol-1-yl)-3-methoxypropan-2-ol] (AIM) (2-hydroxy-3-methoxypropyl)-guanidine (G) Hydrolysis - Hydrolyzation Unclear [6]
MR004280 N-hydroxylamine Amine Reduction - Reduction Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1048 Escherichia coli
NFSB_ECOLI
1.5.1.34
[2]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[3]
References
1 Ring formation and hydration effects in electron attachment to misonidazole. Int J Mol Sci. 2019 Sep 6;20(18). pii: E4383.
2 Metronidazole (flagyl) and misonidazole (Ro-07-0582): reduction by facultative anaerobes and cytotoxic action on hypoxic bacteria and mammalian cells in vivo. Br J Cancer Suppl. 1978 Jun;3:132-5.
3 Reductive metabolism and DNA binding of misonidazole
4 Kinetic aspects of misonidazole and its major metabolite in radiotherapy
5 Misonidazole and other hypoxia markers: metabolism and applications
6 Comparative misonidazole metabolism in anaerobic bacteria and hypoxic Chinese hamster lung fibroblast (V-79-473) cells

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