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Compound Detail

CHEMBL13280

FLUNITRAZEPAM
💊 Approved Drug
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💊 Approved Drug
CN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13280
Name FLUNITRAZEPAM
Phase Approved
Structure Type MOL
InChI Key PPTYJKAXVCCBDU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Flunitrazepam N05CD03 RO 5-4200 RO-5-4200 RO-54200 Rohypnol
12
Targets
33
Activities
4
Assay Types
6
PK Parameters
20
Publications
6
Known Names
1
Mechanisms

Molecular Properties

313.3
MW (Da)
2.55
ALogP
4
HBA
0
HBD
75.8
PSA (Ų)
0.63
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn
USAN Stem -azepam
USAN Year 1976

Extended Properties

Molecular Formula C16H12FN3O3
MW 313.29
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.97

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR GABA-A receptor; anion channel ✓ ✓

ATC Classification

N05CD03
flunitrazepam
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Withdrawn
drug misuse
Abuse
Country: France   Year: 1996

Activity Summary

Ki 23 meas. best 8.96
IC50 7 meas. best 8.82
Kd 2 meas. best 8.52
EC50 1 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 8.96 8.72 1.1 3
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
 EC50 8.85 8.85 1.4 1
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 8.82 8.596 1.5 5
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 Ki 8.68 8.68 2.1 2
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2
CHEMBL4523641
 Ki 8.68 8.68 2.1 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 8.66 8.66 2.2 2
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
 Ki 8.66 8.535 2.2 2
GABA A receptor alpha-2/beta-2/gamma-2
CHEMBL2111413
 Ki 8.6 8.6 2.5 1
Gamma-aminobutyric acid receptor subunit alpha-5
CHEMBL5112
 Kd 8.52 8.52 3.0 1
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Kd 8.35 8.35 4.5 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 8.35 8.31 4.5 3
GABA A receptor alpha-3/beta-2/gamma-2
CHEMBL2111339
 Ki 8.35 8.35 4.5 1
Unchecked
CHEMBL612545
 Ki 8.29 8.2457 5.1 7

Pharmacokinetic Data

Parameter Value Units Species
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 5.01 uL.min-1.(10^6cells)-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.17 - Homo sapiens
MRT 23.0 hr Homo sapiens
T1/2 25.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 1.1 nM 8.96 Binding affinity evaluated by ability to displace [3H]-Ro-15-1788 from recombina... 10890169
GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 = 1.4 nM 8.85 Activity at human GABAA alpha-1-beta-2-gamma-2S327 receptor in HEK293 cells expr... 17875639
GABA-A receptor; anion channel IC50 = 1.5 nM 8.82 Displacement of [3H]diazepam from GABA-A Benzodiazepine receptor of rat forebrai... 1846920
GABA-A receptor; anion channel IC50 = 1.7 nM 8.77 Inhibition of [3H]diazepam binding to GABA-A benzodiazepine receptor of rat brai... 2848124
GABA-A receptor; anion channel IC50 = 1.7 nM 8.77 Displacement of [3H]diazepam from rat brain GABA-A benzodiazepine receptor 2885419
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.1 nM 8.68 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 2.1 nM 8.68 Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyri... 9651158
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2 Ki = 2.1 nM 8.68 Displacement of [3H]flunitrazepam from human recombinant alpha5beta2gamma2 GABAA... 35218882
GABA-A receptor; alpha-1/beta-2/gamma-2 Ki = 2.2 nM 8.66 Displacement of [3H]flunitrazepam from human recombinant alpha1beta2gamma2 GABAA... 35218882
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 2.2 nM 8.66 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 2.2 nM 8.66 Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta... 9651158
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 2.5 nM 8.6 Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor ... 10633039
GABA A receptor alpha-2/beta-2/gamma-2 Ki = 2.5 nM 8.6 Displacement of [3H]flunitrazepam from human recombinant alpha2beta2gamma2 GABAA... 35218882
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 2.5 nM 8.6 Binding affinity measured using LtK- cell membranes expressing GABA alpha-2-beta... 9651158
Gamma-aminobutyric acid receptor subunit alpha-5 Kd = 3.0 nM 8.52 Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor 18537233
GABA-A receptor; anion channel IC50 = 3.0 nM 8.52 Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor of rat cer... 3037081
GABA-A receptor; alpha-1/beta-2/gamma-2 Ki = 3.9 nM 8.41 Binding affinity evaluated by ability to displace [3H]Ro-151788 from recombinant... 10890169
Gamma-aminobutyric acid receptor subunit alpha-1 Kd = 4.5 nM 8.35 Binding affinity to GABAA alpha-1-beta-2-gamma-2 receptor 18537233
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 4.5 nM 8.35 Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor... 10633039
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 4.5 nM 8.35 Binding affinity measured using LtK- cell membranes expressing GABA alpha-3-beta... 9651158

Literature References

PubMed DOI Target Context # Activities
7381845 10.1021/jm00178a018 ADMET 5
26982523 10.1021/acs.jmedchem.6b00034 Unchecked 5
21751815 10.1021/jm2001597 Unchecked 5
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
17875639 10.1074/jbc.m707233200 Unchecked 4
926122 10.1021/jm00219a019 Mus musculus 4
18637672 10.1021/jm8002944 Unchecked 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
2202830 10.1021/jm00171a037 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
20014752 10.1021/tx900326k Hepatotoxicity 3
17875639 10.1074/jbc.m707233200 Gamma-aminobutyric acid receptor subunit alpha-1 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
17875639 10.1074/jbc.m707233200 GABA-A receptor; alpha-1/beta-2/gamma-2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2

Data from ChEMBL 36 via Core Engine