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

General Information of Drug (ID: DR1166)
Drug Name
Nitrazepam
Synonyms
Apodorm; Benzalin; Calsmin; Cerson; Dormin-5; Dormo-Puren; Dumolid; Eatan N; Epibenzalin; Epinelbon; Eunoctin; Gerson; Hipnax; Hipsal; Ibrovek; Imeson; Imesont; Magadon; Megadon; Mitidin; Mogadan; Mogadon; Mogadone; N-Desmethylnimetazepam; Nelbon; Nelmat; Neozepam; Neuchlonic; Nitrados; Nitrazepamum; Nitrazepamum [INN-Latin]; Nitrenpax; Paxisyn; Pelson; Persopit; Radedorm; Relact; Remnos; Ro 4-5360; Somitran; Somnite; Sonebon; Sonnolin; Trazenin; Unisomnia; nitrazepam; 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one; 146-22-5; Eatan; LA 1; Surem
Indication Insomnia [ICD11: 7A00] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 281.27 Topological Polar Surface Area 87.3
Heavy Atom Count 21 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4506
PubChem SID
9690 ; 107320 ; 597368 ; 5055565 ; 5073767 ; 5081626 ; 6057695 ; 7847597 ; 7849647 ; 7980131 ; 8152775 ; 10508332 ; 11210457 ; 12326898 ; 14824476 ; 24897666 ; 29215277 ; 29223600 ; 46386691 ; 46505806 ; 47515481 ; 48211546 ; 48334666 ; 48416331 ; 49884256 ; 50086824 ; 50841107 ; 56313772 ; 57322305 ; 81093238 ; 85174552 ; 87467573 ; 87687912 ; 88194890 ; 92214795 ; 92308349 ; 92720560 ; 92729730 ; 103174569 ; 103931581 ; 104306604 ; 106801912 ; 115998634 ; 117378604 ; 124658968 ; 124813337 ; 125341242 ; 126619885 ; 126654716 ; 126667398
ChEBI ID
CHEBI:7581
CAS Number
146-22-5
TTD Drug ID
D0T5WK
Formula
C15H11N3O3
Canonical SMILES
C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3
InChI
1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)
InChIKey
KJONHKAYOJNZEC-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
7- AMlNO NlTRAZEPAM DM003357 N. A. Reduction - Reduction 1 [2] , [3]
7-NITROXY NITRAZEPAM DM003354 N. A. Unclear 1 [2]
7- A MlNO NlTRAZEPAM DM003355 N. A. Unclear 2 [2]
7-ACETAMlDO NlTRAZEPAM DM003356 N. A. Unclear 2 [2]
7-acetylamino nitrazepam DM003358
96190
Conjugation - Acetylation 2 [2] , [3]
7-ACETAMlDO NlTRAZEPAM DM003356 N. A. Unclear 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003789 Nitrazepam 7-NITROXY NITRAZEPAM Unclear Unclear [2]
MR003792 Nitrazepam 7- AMlNO NlTRAZEPAM Reduction - Reduction AOX1 [2], [3]
MR003793 7- AMlNO NlTRAZEPAM 7-ACETAMlDO NlTRAZEPAM Unclear Unclear [2]
MR003794 7- AMlNO NlTRAZEPAM 7-acetylamino nitrazepam Conjugation - Acetylation NAT2 [2], [3]
MR003790 7-NITROXY NITRAZEPAM 7- A MlNO NlTRAZEPAM Unclear Unclear [2]
MR003791 7- A MlNO NlTRAZEPAM 7-ACETAMlDO NlTRAZEPAM Unclear Unclear [2]
⏷ Show the Full List of 6 MR(s)
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] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[2] , [3]
Nitroreductase (NTR) DME1070 Clostridium leptum
A0A412R9E4_9FIRM
1.5.1.39
[5]
Nitroreductase (NTR) DME1958 Prevotella copri
A0A413TUJ8_9BACT
1.5.1.39
[6]
Nitroreductase (NTR) DME1968 Salmonella typhimurium
A0A5K1UB29_SALTM
1.5.1.39
[7] , [8]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1098 Escherichia coli
NFSA_ECOLI
1.5.1.38
[9]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1971 Salmonella enterica
NFSA_SALTY
1.5.1.38
[10]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1048 Escherichia coli
NFSB_ECOLI
1.5.1.34
[11]
⏷ Show the Full List of 9  DME(s)
References
1 ClinicalTrials.gov (NCT00374777) A Double-blind, Group-comparison P-III Study With Zolpidem MR Using Placebo and Nitrazepam in Insomnia Patients.
2 Production of superoxide during the metabolism of nitrazepam
3 Identification of enzymes responsible for nitrazepam metabolism and toxicity in human
4 Prediction of metabolic clearance using fresh human hepatocytes: comparison with cryopreserved hepatocytes and hepatic microsomes for five benzodiazepines. Xenobiotica. 2008 Apr;38(4):353-67.
5 Reduction of nitrazepam by Clostridium leptum, a nitroreductase-producing bacterium isolated from the human intestinal tract. Clin Infect Dis. 1997 Sep;25 Suppl 2:S121-2.
6 Distinct genetic and functional traits of human intestinal Prevotella copri strains are associated with different habitual diets. Cell Host Microbe. 2019 Mar 13;25(3):444-453.e3.
7 Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
8 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter
9 Biochemical characterization of NfsA, the Escherichia coli major nitroreductase exhibiting a high amino acid sequence homology to Frp, a Vibrio harveyi flavin oxidoreductase. J Bacteriol. 1996 Aug;178(15):4508-14.
10 Identification and characterization of SnrA, an inducible oxygen-insensitive nitroreductase in Salmonella enterica serovar Typhimurium TA1535. Mutat Res. 2002 Oct 31;508(1-2):59-70.
11 Conversion of NfsB, a minor Escherichia coli nitroreductase, to a flavin reductase similar in biochemical properties to FRase I, the major flavin reductase in Vibrio fischeri, by a single amino acid substitution. J Bacteriol. 1996 Aug;178(15):4731-3.

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