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

General Information of Drug (ID: DR0712)
Drug Name
Flunitrazepam
Synonyms
Flunitrazepam [USAN:INN:BAN:JAN]; Flunitrazepamum; Flunitrazepamum [INN-Latin]; Flunitrazepan; Narcozep; Primun; Ro 5-4200; Rohypnol; Roipnol; flunitrazepam; 1622-62-4; 2H-1,4-Benzodiazepin-2-one, 5-(2-fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-; 5-(2-fluorophenyl)-1-methyl-7-nitro-3H-1,4-benzodiazepin-2-one; 5-(o-Fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one; BRN 0702691; CCRIS 5287; EINECS 216-597-8; HSDB 6960; UNII-620X0222FQ; [3H]flunitrazepam
Indication Insomnia [ICD11: 7A00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 313.28 Topological Polar Surface Area 78.5
Heavy Atom Count 23 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3380
PubChem SID
529943 ; 5367816 ; 6018772 ; 7848293 ; 7849646 ; 8150136 ; 8152151 ; 10509780 ; 11336156 ; 11361395 ; 11462367 ; 15494069 ; 24894993 ; 29222515 ; 46504553 ; 47291209 ; 48416024 ; 49884241 ; 53786877 ; 56413166 ; 57321765 ; 71821460 ; 79315430 ; 99302069 ; 103174540 ; 104303344 ; 109613212 ; 126691439 ; 128950759 ; 128950760 ; 131300954 ; 134338207 ; 134961908 ; 134979679 ; 136949637 ; 137002941 ; 141004720 ; 143054817 ; 160839433 ; 160964789 ; 162956355 ; 163402580 ; 164788746 ; 178101010 ; 178101176 ; 179148568 ; 184547588 ; 196104471 ; 198960206 ; 198991798
ChEBI ID
CHEBI:31622
CAS Number
1622-62-4
TTD Drug ID
D0W2NM
Formula
C16H12FN3O3
Canonical SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3F
InChI
1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3
InChIKey
PPTYJKAXVCCBDU-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
3-hydroxyflunitrazepam DM006679
128908
Oxidation - Hydrolyzationn 1 [7]
7-amino-unitrazepam DM006680 N. A. Reduction - Reduction 1 [6] , [8] , [9]
Desmethylflunitrazepam DM006678
520217
Oxidation - Demethylation 1 [7] , [9] , [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007193 Flunitrazepam Desmethylflunitrazepam Oxidation - Demethylation CYP2C19 ... [7], [9], [10]
MR007194 Flunitrazepam 3-hydroxyflunitrazepam Oxidation - Hydrolyzationn CYP3A4 [7]
MR007195 Flunitrazepam 7-amino-unitrazepam Reduction - Reduction nfsB [6], [8], [9]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1048 Escherichia coli
NFSB_ECOLI
1.5.1.34
[6]
⏷ Show the Full List of 7  DME(s)
References
1 ClinicalTrials.gov (NCT02648776) Risk and Benefit Assessment of Hypnotic Agents for Sleep Disorders Among Elderly.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam. Drug Metab Dispos. 2001 Feb;29(2):133-40.
4 Cytochrome P450 3A4 and benzodiazepines. Seishin Shinkeigaku Zasshi. 2003;105(5):631-42.
5 The role of cytochrome P450 2C19 activity in flunitrazepam metabolism in vivo. J Clin Psychopharmacol. 2003 Apr;23(2):169-75.
6 Structure-based development of bacterial nitroreductase against nitrobenzodiazepine-induced hypnosis. Biochem Pharmacol. 2012 Jun 15;83(12):1690-9.
7 Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):460-5.
8 NADPH-cytochrome P-450 reductase is involved in flunitrazepam reductive metabolism in Hep G2 and Hep 3B cells
9 Flunitrazepam oxidative metabolism in human liver microsomes: involvement of CYP2C19 and CYP3A4. Xenobiotica. 1999 Oct;29(10):973-86.
10 Lack of interaction of buprenorphine with flunitrazepam metabolism

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