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

General Information of Drug (ID: DR2213)
Drug Name
AI3-23606
Synonyms
AMOT0097; FUBFWTUFPGFHOJ-UHFFFAOYSA-N; Furan, 2-nitro-; Furan, nitro-; LS-70264; Nitrofuran; Nitrofuran (VAN); Q-103253; Q27116311; TC-155289; TRA0000166; ZINC1689931; 17EZI4D981; 2-NITROFURAN; 2-Nitrofuran, 97%; 2-Nitrofurane; 27194-24-7; 5-17-01-00296 (Beilstein Handbook Reference); 5-Nitrofuran; 609-39-2; 9109AB; AI3-23606; AKOS015900364; AM20100483; ANW-66544; BCP23236; BRN 0112523; C-51401; C14414; CHEBI:34890; CTK1A5052; DB-002205; FCH1116845; FT-0632538; H118; NSC 59983; NSC-59983; NSC59983; SCHEMBL30623; UNII-17EZI4D981
Indication Trypanosomiasis [ICD11: 1F51] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 113.07 Topological Polar Surface Area 59
Heavy Atom Count 8 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
11865
ChEBI ID
CHEBI:34890
CAS Number
609-39-2
Formula
C4H3NO3
Canonical SMILES
C1=COC(=C1)[N+](=O)[O-]
InChI
1S/C4H3NO3/c6-5(7)4-2-1-3-8-4/h1-3H
InChIKey
FUBFWTUFPGFHOJ-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
AI3-23606 M1 PDM007496
54348130
Reduction - Nitroreduction of nitroarene to nitrosoarene 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Nitroreductase (NTR) DME1247 Enterobacter cloacae
NFSB_ENTCL
1.5.1.39
[2]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1971 Salmonella enterica
NFSA_SALTY
1.5.1.38
[3]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1617 Salmonella enterica
NFSB_SALTY
1.5.1.34
[3]
Retro-nitroreductase (rNR) DME1584 Enterobacter cloacae
A0A0H3CM55_ENTCC
1.5.1.34
[4]
References
1 The toxicity of nitrofuran compounds on melanoma and neuroblastoma cells is enhanced by Olaparib and ameliorated by melanin pigment. DNA Repair (Amst). 2013 Nov;12(11):1000-6.
2 Overexpression, isotopic labeling, and spectral characterization of Enterobacter cloacae nitroreductase. Protein Expr Purif. 1998 Jun;13(1):53-60.
3 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.
4 Retro-nitroreductase, a putative evolutionary precursor to Enterobacter cloacae strain 96-3 nitroreductase. Antioxid Redox Signal. 2001 Oct;3(5):747-55.

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