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Compound Detail

CHEMBL452

CLONAZEPAM
💊 Approved Drug
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💊 Approved Drug
O=C1CN=C(c2ccccc2Cl)c2cc([N+](=O)[O-])ccc2N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL452
Name CLONAZEPAM
Phase Approved
Structure Type MOL
InChI Key DGBIGWXXNGSACT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Clonazepam Clonazepam civ Klonopin Klonopin rapidly disintegrating NSC-179913 Ravotril Rivatril Rivotril RO 5-4023 RO-5-4023 RO-54023
5
Targets
15
Activities
3
Assay Types
15
PK Parameters
20
Publications
11
Known Names
15
Indications
1
Mechanisms

Molecular Properties

315.7
MW (Da)
3.04
ALogP
4
HBA
1
HBD
84.6
PSA (Ų)
0.68
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -azepam
USAN Year 1969

Extended Properties

Molecular Formula C15H10ClN3O3
MW 315.72
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.87

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 ✓ ✓

Indications

Epilepsy Panic Disorder Seizures Anxiety Dementia Depressive Disorder Epilepsia Partialis Continua Epilepsy, Tonic-Clonic Pain Schizophrenia Status Epilepticus Marijuana Abuse REM Sleep Behavior Disorder Neuralgia Burning Mouth Syndrome

ATC Classification

N03AE01
clonazepam
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Drug Warnings

Black Box Warning
General Warning
Country: United States
Black Box Warning
misuse
Country: United States

Activity Summary

Ki 8 meas. best 9.07
IC50 5 meas. best 8.77
EC50 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; anion channel
CHEMBL2093872
 Ki 9.07 9.07 0.8 1
GABA-A receptor; anion channel
CHEMBL2094107
 Ki 9.07 9.07 0.8 3
Translocator protein
CHEMBL2419
 Ki 9.07 9.07 0.8 1
Unchecked
CHEMBL612545
 Ki 9.07 8.7233 0.8 3
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 8.77 8.77 1.7 2
Unchecked
CHEMBL612545
 IC50 8.31 8.31 4.9 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.88 mL.min-1.kg-1 Homo sapiens
CL 0.88 mL.min-1.kg-1 Homo sapiens
CL 0.9 mL.min-1.kg-1 Homo sapiens
CL 0.88 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 14.0 mL.min-1.kg-1 Macaca
CL 21.0 mL.min-1.kg-1 Rattus norvegicus
CL 3.72 uL.min-1.(10^6cells)-1 Homo sapiens
F 80.0 % Homo sapiens
F 90.0 % Homo sapiens
Fu 0.15 - Homo sapiens
Fu 0.15 - Homo sapiens
MRT 55.0 hr Homo sapiens
T1/2 38.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; anion channel Ki = 0.85 nM 9.07 In vitro inhibition of [3H]-Ro- 15-1788 binding to GABA-A Benzodiazepine recepto... 9748357
GABA-A receptor; anion channel Ki = 0.85 nM 9.07 Inhibition of [3H]- flumazenil binding to benzodiazepine receptor in bovine brai... 11428922
GABA-A receptor; anion channel Ki = 0.85 nM 9.07 Displacement of [3H]- Ro.15-1788 from GABA-A central Benzodiazepine receptor (Bz... 10633040
GABA-A receptor; anion channel Ki = 0.85 nM 9.07 Displacement of [3H]flumazenil from bovine benzodiazepine receptor GABA-A channe... 15828832
Unchecked Ki = 0.85 nM 9.07 Displacement of [3H]flumazenil from benzodiazepine receptor in bovine brain memb... 17335185
Translocator protein Ki = 0.85 nM 9.07 Binding affinity to bovine brain membrane BzR assessed as inhibition constant 33764065
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; anion channel IC50 = 1.7 nM 8.77 Inhibition of [3H]diazepam binding to GABA-A benzodiazepine receptor of rat brai... 2848124
Unchecked Ki = 2.0 nM 8.7 Displacement of [3H]flunitrazepam from benzodiazepine receptor 8496700
Unchecked Ki = 4.018 nM 8.4 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -
Unchecked IC50 = 4.932 nM 8.31 DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 523
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
15920768 10.1002/jps.20373 ADMET 8
2170646 10.1021/jm00172a015 Mus musculus 6
18426954 10.1124/dmd.108.020479 ADMET 4
16019946 10.1080/00498250400028197 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
926122 10.1021/jm00219a019 Mus musculus 4
20869876 10.1016/j.bmc.2010.08.052 Albumin 4
24568674 10.1021/jm401864b Albumin 3
32877805 10.1016/j.ejmech.2020.112709 Unchecked 3
9748357 10.1021/jm9800301 GABA-A receptor; anion channel 3
10633040 10.1021/jm991131h GABA-A receptor; anion channel 3
19275170 10.1021/jm801652d Mus musculus 3
19275170 10.1021/jm801652d Rattus norvegicus 3
26483200 10.1016/j.bmcl.2015.09.045 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3

Data from ChEMBL 36 via Core Engine