Nitrazepam

Details

• Internal ID: 1f8f6b27-f530-4982-b952-09e7fd092945
• Taxonomy: Organoheterocyclic compounds > Benzodiazepines > 1,4-benzodiazepines
• IUPAC Name: 7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• SMILES (Canonical): C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3
• SMILES (Isomeric): 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)
• InChI Key: KJONHKAYOJNZEC-UHFFFAOYSA-N
• Popularity: 3,880 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₁N₃O₃
• Molecular Weight: 281.27 g/mol
• Exact Mass: 281.08004122 g/mol
• Topological Polar Surface Area (TPSA): 87.30 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Benzalin
• 146-22-5
• Neozepam
• Imeson
• Mogadon
• Remnos
• Neuchlonic
• Apodorm
• Calsmin
• Eunoctin
• Imesont
• Nitrados
• Radedorm
• Sonebon
• Trazenin
• Hipnax
• Hipsal
• Nelmat
• Surem
• Epibenzalin
• Epinelbon
• Nitrenpax
• Somitran
• Sonnolin
• Unisomnia
• Cerson
• Dumolid
• Nelbon
• Paxisyn
• Pelson
• Relact
• N-Desmethylnimetazepam
• Persopit
• Gerson
• Ibrovek
• Eatan
• Dormin-5
• Nitrazepamum
• 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
• Ro 4-5360
• Mogadone
• Magadon
• Megadon
• Mogadan
• Ro 5-3059
• Nitrazepamum [INN-Latin]
• 7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• LA 1
• NSC-58775
• 7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one
• 7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• 2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-nitro-5-phenyl-
• S 2000
• 2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-on
• 7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
• Dormo-Puren
• Mitidin
• 9CLV70W7HS
• CHEMBL13209
• Eatan N
• CHEBI:7581
• DTXSID5023372
• Somnite
• N05CD02
• NSC58775
• Ro-45360
• Ro-53059
• NCGC00159358-02
• 2,3-dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one
• Calsamin
• Eunoktin
• Ipersed
• Nitravet
• Nitrempax
• Noctesed
• Pacisyn
• Somnased
• Somnibel
• RO-4-5360
• RO-5-3059
• LA 1 (VAN)
• Dormicum (anticonvulsant)
• DTXCID803372
• 7-Nitro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
• Nitrazepam [USAN:INN:BAN:JAN]
• Nitrazepam (TN)
• Benzalin (TN)
• CAS-146-22-5
• SMR000058302
• CCRIS 1931
• EINECS 205-665-2
• NSC 58775
• UNII-9CLV70W7HS
• BRN 0757185
• DEA No. 2834
• ISOPROPYLACETATE/NITRAZEPAM
• Ro 53-60
• NITRAZEPAM [MI]
• NITRAZEPAM [INN]
• NITRAZEPAM [JAN]
• NITRAZEPAM [USAN]
• ChemDiv1_022312
• NITRAZEPAM [MART.]
• NITRAZEPAM [WHO-DD]
• NITRAZEPAM [WHO-IP]
• Oprea1_476234
• SCHEMBL35202
• 5-24-04-00344 (Beilstein Handbook Reference)
• MLS001304053
• MLS001424061
• Nitrazepam (JP17/USAN/INN)
• HMS650G04
• KJONHKAYOJNZEC-UHFFFAOYSA-
• NITRAZEPAM [EP MONOGRAPH]
• 1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
• HMS2051F19
• HMS2272G03
• HMS3393F19
• 7-Nitro-1,4-benzodiazepin-2-one
• Nitrazepam, 1mg/ml in Acetonitrile
• NITRAZEPAMUM [WHO-IP LATIN]
• Tox21_111601
• BDBM50020856
• PDSP1_000120
• PDSP2_000120
• AKOS002254707
• Nitrazepam 0.1 mg/ml in Acetonitrile
• Nitrazepam 1.0 mg/ml in Acetonitrile
• Tox21_111601_1
• WLN: T67 GMV JN IHJ CNW KR
• AB02342
• AC-4537
• CCG-100977
• DB01595
• NC00227
• NCGC00159358-03
• 2H-1, 1,3-dihydro-7-nitro-5-phenyl-
• 7-Nitro-5-phenyl-2,4-benzodiazepin-2-one
• C07487
• D00531
• A808471
• Q410078
• 7-nitro-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one
• Nitrazepam, British Pharmacopoeia (BP) Reference Standard
• Nitrazepam, European Pharmacopoeia (EP) Reference Standard
• (Z)-7-nitro-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one
• 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepine-2-one
• 7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one #
• InChI=1/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)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9804	98.04%
Caco-2	-	0.5652	56.52%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.9571	95.71%
Subcellular localzation	Mitochondria	0.5346	53.46%
OATP2B1 inhibitior	-	0.8465	84.65%
OATP1B1 inhibitior	+	0.9189	91.89%
OATP1B3 inhibitior	+	0.9369	93.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7930	79.30%
P-glycoprotein inhibitior	-	0.9378	93.78%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.7243	72.43%
CYP2C9 substrate	-	0.6114	61.14%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	+	0.6791	67.91%
CYP2C9 inhibition	-	0.6133	61.33%
CYP2C19 inhibition	+	0.5682	56.82%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	+	0.7569	75.69%
CYP2C8 inhibition	-	0.9490	94.90%
CYP inhibitory promiscuity	+	0.5645	56.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6310	63.10%
Carcinogenicity (trinary)	Non-required	0.5498	54.98%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9255	92.55%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.8599	85.99%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7620	76.20%
Acute Oral Toxicity (c)	III	0.7450	74.50%
Estrogen receptor binding	+	0.7860	78.60%
Androgen receptor binding	+	0.9288	92.88%
Thyroid receptor binding	-	0.5772	57.72%
Glucocorticoid receptor binding	+	0.8289	82.89%
Aromatase binding	+	0.8984	89.84%
PPAR gamma	+	0.8519	85.19%
Honey bee toxicity	-	0.9019	90.19%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7634	76.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	97.90%	89.76%
CHEMBL2581	P07339	Cathepsin D	97.81%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.49%	86.33%
CHEMBL3524	P56524	Histone deacetylase 4	95.93%	92.97%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.09%	95.56%
CHEMBL1255126	O15151	Protein Mdm4	93.55%	90.20%
CHEMBL4578	Q14680	Maternal embryonic leucine zipper kinase	88.94%	81.58%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	88.49%	95.72%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	87.29%	92.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.94%	94.62%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	85.54%	85.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.32%	99.23%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.23%	96.25%
CHEMBL1937	Q92769	Histone deacetylase 2	84.16%	94.75%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	84.04%	100.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.03%	93.81%
CHEMBL230	P35354	Cyclooxygenase-2	83.18%	89.63%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.04%	96.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.93%	93.40%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.22%	92.88%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	81.13%	88.84%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.05%	96.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 4506
• LOTUS: LTS0035807
• wikiData: Q410078