FLUNITRAZEPAM

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC N05CD03
UNII 620X0222FQ
EPA CompTox DTXSID7023065

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 Reference
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
CONTENTS