Details of the Drug

General Information of Drug (ID: DMEGIQ6)

Drug Name
Nitrazepam
Synonyms
Alodorm; Apodorm; Benzalin; Calsamin; Calsmin; Cerson; Dormalon; Dumolid; Eatan; Epibenzalin; Epinelbon; Eunoctin; Eunoktin; Gerson; Hipnax; Hipsal; Ibrovek; Imadorm; Imeson; Imesont; Ipersed; Magadon; Megadon; Mitidin; Mogadan; Mogadon; Mogadone; Nelbon; Nelmat; Neozepam; Neuchlonic; Nitrados; Nitravet; Nitrazadon; Nitrazep; Nitrazepamum; Nitrempax; Nitrenpax; Nitrodiazepam; Noctesed; Novanox; Pacisyn; Paxisyn; Pelson; Persopit; Radedorm; Relact; Remnos; Serenade; Somitran; Somnased; Somnibel; Somnite; Sonebon; Sonnolin; Surem; Trazenin; Unisomnia; Aliud Brand of Nitrazepam; Allphar Brand of Nitrazepam; Alphapharma Brand of Nitrazepam; Alpharma Brand of Nitrazepam; Alter Brand of Nitrazepam; CSP Brand of Nitrazepam; DDSA Brand of Nitrazepam; Dermatech Brand of Nitrazepam; Desitin Brand of Nitrazepam; Dormicum Brand of Nitrazepam; Eatan N; ICN Brand of Nitrazepam; Neuraxpharm Brand of Nitrazepam; Nitrazepam AL; Norgine Brand of Nitrazepam; Pfleger Brand of Nitrazepam; Protea Brand of Nitrazepam; Rhoxalpharma Brand of Nitrazepam; Sandoz nitrazepam; Scheurich Brand of Nitrazepam; Sonebon Tofraniln A; Taurus Brandof Nitrazepam; United Drug Brand of Nitrazepam; Wernigerode Brand of Nitrazepam; LA 1; S 2000; Alodorm (TN); Apo-nitrazepam tablets BP; Apodorm (TN); Arem (TN); Benzalin (TN); Cavodan (TN); Ct-Arzneimittel Brand of Nitrazepam; Dima (TN); Dormalon (TN); Dormicum (anticonvulsant); Dormigen (TN); Dormin-5; Dormo-Puren; Dumolid (TN); Eatan N (TN); Eunoctin (TN); Hypnotex (TN); ISOPROPYLACETATE/NITRAZEPAM; Imeson (TN); Insoma (TN); Insomin (TN); Ipersed (TN); LA 1 (VAN); Mitidin (TN); Mogadan (TN); Mogadon (TN); N-Desmethylnimetazepam; Nitavan (TN); Nitepam (TN); Nitrados (TN); Nitrapan (TN); Nitravet (TN); Nitrazadon (TN); Nitrazep (TN); Nitrazepam (TN); Nitrazepam Capsules BP 1993 (TN); Nitrazepam Oral Suspension BP 1993 (TN); Nitrazepam Tablets BP 1993 (TN); Nitrazepam-10; Nitrazepam-5; Nitrazepam-neuraxpharm; Nitrazepamum [INN-Latin]; Nitrazepan (TN); Nitrazepol (TN); Nitredon (TN); Nitrosun (TN); Novanox (TN); Numbon (TN); Onirema (TN); Ormodon (TN); Pacisyn (TN); Paxadorm (TN); Pelson (TN); Pelsonfilina (TN); Protraz (TN); Radedorm (TN); Remnos (TN); Rhoxal-nitrazepam; Ro 4-5360; Ro 5-3059; Ro 53-60; Serenade (TN); Somnibel N (TN); Somnipar (TN); Somnite (TN); Sonebon (TN); Sonotrat (TN); Surem (TN); Tri (TN); Unisomnia (TN); Dormo-Puren (TN); Nitrazepam (JP15/USAN/INN); Nitrazepam [USAN:INN:BAN:JAN]; 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one; 2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-on; 7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one; 7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Indication
Disease Entry ICD 11 Status REF
Epilepsy 8A60-8A68 Approved [1]
Insomnia 7A00-7A0Z Approved [1]
Therapeutic Class
Antianxiety Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 281.27
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Bioavailability
The bioavailability of drug is 53-94% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.86 mL/min/kg [3]
Elimination
0.5% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 - 38 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.01579 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.13% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.7 L/kg [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0254 mg/mL [2]
Chemical Identifiers
Formula
C15H11N3O3
IUPAC Name
7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Canonical SMILES
C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3
InChI
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
Cross-matching ID
PubChem CID
4506
ChEBI ID
CHEBI:7581
CAS Number
146-22-5
DrugBank ID
DB01595
TTD ID
D0T5WK
INTEDE ID
DR1166
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
GABA(A) receptor alpha-1 (GABRA1) TT1MPAY GBRA1_HUMAN Antagonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DE0QLUZ NFSB_ECOLI Substrate [7]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DEDPI65 NFSA_ECOLI Substrate [8]
Nitroreductase (NTR) DE0K82S A0A5K1UB29_SALTM Substrate [9], [10]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DEX5D46 NFSA_SALTY Substrate [11]
Nitroreductase (NTR) DEAVXGM A0A412R9E4_9FIRM Substrate [12]
Nitroreductase (NTR) DEGV7K0 A0A413TUJ8_9BACT Substrate [13]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [14]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [14]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [14]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Nitrazepam, 2008. eduDrugs.
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
6 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.
7 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.
8 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.
9 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.
10 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter
11 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.
12 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.
13 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.
14 Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.