FLUNITRAZEPAM


Synonyms	Flunitrazepam N05CD03 RO 5-4200 RO-5-4200 RO-54200 Rohypnol
Status
Molecule Category	UNKNOWN
ATC	N05CD03
UNII	620X0222FQ
EPA CompTox	DTXSID7023065


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PPTYJKAXVCCBDU-UHFFFAOYSA-N
Smiles	CN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21
InChI	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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H12FN3O3
Molecular Weight	313.29
AlogP	2.55
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	2.0
Polar Surface Area	75.81
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
GABA-A receptor; anion channel positive allosteric modulator	POSITIVE ALLOSTERIC MODULATOR	PubMed Other PubMed PubMed


Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit pi Organism : Homo sapiens O00591 ENSG00000094755









Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit delta Organism : Homo sapiens O14764 ENSG00000187730











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-1 Organism : Homo sapiens P14867 ENSG00000022355











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit beta-1 Organism : Homo sapiens P18505 ENSG00000163288








Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit gamma-2 Organism : Homo sapiens P18507 ENSG00000113327











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit beta-3 Organism : Homo sapiens P28472 ENSG00000166206











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-5 Organism : Homo sapiens P31644 ENSG00000186297











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-3 Organism : Homo sapiens P34903 ENSG00000011677











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-2 Organism : Homo sapiens P47869 ENSG00000151834











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit beta-2 Organism : Homo sapiens P47870 ENSG00000145864











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-4 Organism : Homo sapiens P48169 ENSG00000109158










Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit epsilon Organism : Homo sapiens P78334 ENSG00000102287









Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit alpha-6 Organism : Homo sapiens Q16445 ENSG00000145863










Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit gamma-1 Organism : Homo sapiens Q8N1C3 ENSG00000163285










Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit gamma-3 Organism : Homo sapiens Q99928 ENSG00000182256











Protein: GABA-A receptor; anion channel Description: Gamma-aminobutyric acid receptor subunit theta Organism : Homo sapiens Q9UN88 ENSG00000268089

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor	1	2-8	3	1-3	-

Assay Description	Organism	Bioactivity
Displacement of [3H]diazepam from rat brain GABA-A benzodiazepine receptor	Rattus norvegicus	1.7 nM
Inhibition of [3H]diazepam binding to GABA-A benzodiazepine receptor of rat brain	Rattus norvegicus	1.7 nM
Displacement of [3H]beta-CCE from GABA-A benzodiazepine receptor of rat cerebral cortex membranes	Rattus norvegicus	8.0 nM
Displacement of [3H]diazepam from GABA-A Benzodiazepine receptor of rat forebrain	Rattus norvegicus	1.5 nM
Binding affinity evaluated by ability to displace [3H]Ro-151788 from recombinant human Gamma-aminobutyric acid A receptor alpha-1-beta-2-gamma-2 expressed in L(tk-)cells	None	3.9 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-1-beta-3-gamma-2	None	2.2 nM
Binding affinity evaluated by ability to displace [3H]-Ro-15-1788 from recombinant human Gamma-aminobutyric acid A receptor alpha-2-beta-3-gamma-2 expressed in L(tk-)cells	None	1.1 nM
Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-2-beta-3-gamma-2	None	2.5 nM
Binding affinity evaluated by ability to displace [3H]Ro-151788 from recombinant human Gamma-aminobutyric acid A receptor alpha-3-beta-3-gamma-2 expressed in L(tk-)cells	None	5.9 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-3-beta-3-gamma-2	None	4.5 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-5-beta-3-gamma-2	None	2.1 nM
Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyric acid A receptor alpha-5-beta-3-gamma-2	None	2.1 nM
Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta-3-gamma-2 receptor	None	2.2 nM
Binding affinity measured using LtK- cell membranes expressing GABA alpha-2-beta-3-gamma-2 receptor	None	2.5 nM
Binding affinity measured using LtK- cell membranes expressing GABA alpha-3-beta-3-gamma-2 receptor	None	4.5 nM
Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor of rat cerebral cortex membrane	Rattus norvegicus	3.0 nM
Binding affinity to GABAA alpha-1-beta-2-gamma-2 receptor	None	4.5 nM
Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor	None	3.0 nM
Displacement of [3H]flumazenil from CBR in bovine cortical membrane	Bos taurus	5.17 nM
Displacement of [3H]flumazenil from CBR in human cortical membrane	Homo sapiens	6.5 nM
Activity at human GABAA alpha-1-beta-2-gamma-2S327 receptor in HEK293 cells expressing as-PKCepsilon cells assessed as evoked current response by whole cell patch clamp method	Homo sapiens	1.4 nM
Displacement of [3H]flumazenil from central benzodiazepine receptor in rat cerebral cortex membranes at 10 uM after 90 mins by competitive binding assay	Rattus norvegicus	0.0 %
Displacement of [3H]flumazenil from central benzodiazepine receptor in bovine cortical membrane after 90 mins by beta liquid scintillation counting	Bos taurus	5.17 nM
Displacement of [3H]flumazenil from central benzodiazepine receptor in human cortical membrane after 90 mins by beta liquid scintillation counting	Homo sapiens	6.5 nM
Displacement of [3H]-flumazenil from central-type benzodiazepine receptor in bovine cortical membrane after 90 mins by liquid-phase scintillation beta-counting method	Bos taurus	5.2 nM
Displacement of [3H]-flumazenil from central-type benzodiazepine receptor in human cortical membrane after 90 mins by liquid-phase scintillation beta-counting method	Homo sapiens	6.4 nM

Related Entries

Cross References

Resources	Reference
ChEBI	31622
ChEMBL	CHEMBL13280
DrugBank	DB01544
DrugCentral	1202
FDA SRS	620X0222FQ
Human Metabolome Database	HMDB0015510
Guide to Pharmacology	4360
PharmGKB	PA164781320
PubChem	3380
SureChEMBL	SCHEMBL44169
ZINC	ZINC000003812994

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