Compound Detail

CHEMBL12

DIAZEPAM

💊 Approved Drug

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💊 Approved Drug

CN1C(=O)CN=C(c2ccccc2)c2cc(Cl)ccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL12
Name	DIAZEPAM
Phase	Approved
Structure Type	MOL
InChI Key	AAOVKJBEBIDNHE-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Alupram 10 Alupram 2 Alupram 5 Ansiolisina Apozepam Atensine Centrazepam Diacepin Dialar Dialar fte Diastat Diastat acudial +18 more

Targets

231

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

284.8

MW (Da)

3.15

ALogP

HBA

HBD

32.7

PSA (Å²)

0.79

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1963
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

USAN Stem	-azepam
USAN Year	1963

Extended Properties

Molecular Formula	C16H13ClN2O
MW	284.75
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	-0.56

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

Anxiety Anxiety Anxiety Disorders Cerebral Palsy Epilepsy Mental Disorders Psychomotor Agitation Stiff-Person Syndrome Dementia Depressive Disorder Epilepsy, Complex Partial Pain Schizophrenia Seizures Status Epilepticus Vertigo Landau-Kleffner Syndrome Low Back Pain Rotator Cuff Injuries Wounds and Injuries

ATC Classification

N05BA01

diazepam

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning

General Warning

Country: United States

Black Box Warning

misuse

Country: United States

Activity Summary

Ki 127 meas. best 9.05

IC50 77 meas. best 8.6

EC50 19 meas. best 7.46

Kd 8 meas. best 8.76

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Translocator protein CHEMBL2419	Ki	9.05	9.05	0.9	1
Unchecked CHEMBL612545	Ki	8.81	7.8326	1.5	27
Unchecked CHEMBL612545	Kd	8.76	7.005	1.8	2
GABA A receptor alpha-6/beta-2/gamma-2 CHEMBL2111365	Ki	8.68	7.86	2.1	4
Unchecked CHEMBL612545	IC50	8.6	7.9161	2.5	18
GABA-A receptor; anion channel CHEMBL1907607	Ki	8.54	8.0735	2.9	20
GABA-A receptor; anion channel CHEMBL1907607	IC50	8.4	8.0097	4.0	38
GABA-A receptor; anion channel CHEMBL2093872	IC50	8.38	7.37	4.2	6
Gamma-aminobutyric acid receptor subunit gamma-1 CHEMBL296	IC50	8.3	8.3	5.0	1
GABA-A receptor; alpha-2/beta-3/gamma-2 CHEMBL2094130	Ki	8.18	7.8375	6.6	8
GABA A receptor alpha-5/beta-3/gamma-2 CHEMBL2111374	Ki	8.01	7.985	9.8	2
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095167	Ki	8.01	7.8983	9.8	6
GABA-A receptor; anion channel CHEMBL2094107	Ki	8.0	8.0	10.0	4
GABA-A receptor; anion channel CHEMBL2093872	Ki	8.0	8.0	10.0	2
GABA A receptor alpha-3/beta-2/gamma-2 CHEMBL2111339	Ki	8.0	7.89	10.0	3
GABA-A receptor; alpha-5/beta-3/gamma-2 CHEMBL2094122	Ki	7.96	7.958	11.0	5
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2 CHEMBL4523641	Ki	7.96	7.96	11.0	1
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL300	Ki	7.96	7.96	11.0	1
GABA A receptor alpha-1/beta-1/gamma-2 CHEMBL2111392	Ki	7.92	7.92	12.0	1
GABA-A receptor; anion channel CHEMBL2094133	IC50	7.92	7.92	12.0	1
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095172	Ki	7.92	7.8867	12.0	3
GABA-A receptor; alpha-1/beta-3/gamma-2 CHEMBL2094121	Ki	7.89	7.8657	13.0	7
GABA-A receptor; anion channel CHEMBL2094107	IC50	7.89	7.6267	13.0	3
GABA A receptor alpha-3/beta-2/gamma-2 CHEMBL2111343	Ki	7.86	7.825	13.9	4
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL343	Ki	7.85	7.85	14.0	1
Gamma-aminobutyric acid receptor subunit alpha-3 CHEMBL328	Ki	7.82	7.82	15.0	1
GABA-A receptor; alpha-3/beta-3/gamma-2 CHEMBL2094120	Ki	7.82	7.6457	15.0	7
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	Ki	7.82	7.82	15.0	1
Gamma-aminobutyric acid receptor subunit alpha-2 CHEMBL341	Ki	7.82	7.76	15.0	2
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Ki	7.8	7.8	16.0	1
Gamma-aminobutyric acid receptor subunit alpha-3 CHEMBL3026	Ki	7.77	7.77	17.0	1
GABA-A receptor; alpha-5/beta-3/gamma-2 CHEMBL2094122	IC50	7.77	7.77	17.0	1
Gamma-aminobutyric acid receptor subunit alpha-2 CHEMBL4956	Ki	7.77	7.77	17.0	1
GABA A receptor alpha-2/beta-2/gamma-2 CHEMBL2111327	Ki	7.7	7.7	20.0	1
GABA A receptor alpha-2/beta-2/gamma-2 CHEMBL2111413	Ki	7.7	7.7	20.0	1
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	Kd	7.64	7.64	23.0	1
GABA-A receptor; alpha-2/beta-3/gamma-2 CHEMBL2094130	EC50	7.46	7.46	35.0	1
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	Kd	7.44	7.44	36.0	1
Cholinesterase CHEMBL5763	Ki	7.37	6.335	43.0	2
GABA-A receptor; alpha-5/beta-3/gamma-2 CHEMBL2094122	EC50	7.35	7.35	45.0	1
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095172	EC50	7.07	7.035	85.0	2
GABA-A receptor; alpha-3/beta-3/gamma-2 CHEMBL2094120	EC50	6.88	6.88	131.0	1
Translocator protein CHEMBL4552	IC50	6.71	6.71	194.0	1
Translocator protein CHEMBL4552	Kd	6.67	6.67	213.0	1
Gamma-aminobutyric acid receptor subunit alpha-6/beta-3/gamma-2 CHEMBL4296054	EC50	6.4	6.28	400.0	2
Fatty acid-binding protein, liver CHEMBL5738	Ki	6.28	6.28	531.0	1
Translocator protein CHEMBL4552	Ki	6.24	6.24	574.0	1
Unchecked CHEMBL612545	EC50	6.16	6.16	700.0	1
Aldo-keto reductase family 1 member C2 CHEMBL5847	IC50	5.62	5.62	2400.0	1
ADMET CHEMBL612558	Kd	5.49	5.49	3240.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	44.0	mL.min-1.kg-1	Rattus norvegicus
CL	30.7	mL.min-1.kg-1	Canis lupus familiaris
CL	0.4	mL.min-1.kg-1	Homo sapiens
CL	113.3	mL.min-1.g-1	Rattus norvegicus
CL	0.43	mL.min-1.kg-1	Homo sapiens
CL	113.3	mL.min-1.g-1	Rattus norvegicus
CL	0.38	mL.min-1.kg-1	Homo sapiens
CL	0.38	mL.min-1.kg-1	Homo sapiens
CL	0.4	mL.min-1.kg-1	Homo sapiens
CL	0.38	mL.min-1.kg-1	Homo sapiens
CL	113.0	uL/min	Rattus norvegicus
CL	5.75	mL.min-1.g-1	Homo sapiens
CL	6.17	uL.min-1.(10^6cells)-1	Homo sapiens
CL	20.0	mL.min	Homo sapiens
CL	27.0	mL.min-1.kg-1	Rattus norvegicus
CL	31.0	mL.min-1.kg-1	Rattus norvegicus
CL	4.6	mL.min-1.g-1	Homo sapiens
CL	0.8	mL.min-1.g-1	Homo sapiens
CL	3.2	mL.min-1.g-1	Homo sapiens
F	80.0	%	Homo sapiens
F	100.0	%	Homo sapiens
F	95.0	%	Homo sapiens
F	97.0	%	Homo sapiens
Fu	0.013	-	-
Fu	0.005	-	-
Fu	0.02	-	Homo sapiens
Fu	0.023	-	Homo sapiens
Fu	0.023	-	Homo sapiens
Fu	0.12	-	Rattus norvegicus
Fu	0.71	-	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Translocator protein	Ki	=	0.9	nM	9.05	Binding affinity to bovine brain membrane BzR assessed as inhibition constant	33764065
Unchecked	Ki	=	1.53	nM	8.81	Displacement of [3H]-flumazenil from benzodiazepine receptor in Sprague-Dawley r...	25564376
Unchecked	Kd	=	1.75	nM	8.76	Displacement of [3H]flumazenil from GABAA/BZD receptor in Sprague-Dawley rat cor...	24530225
Unchecked	Ki	=	1.8	nM	8.74	Inhibition of [3H]diazepam binding to GABA-A central benzodiazepine receptor of ...	2836588
GABA A receptor alpha-6/beta-2/gamma-2	Ki	=	2.1	nM	8.68	Binding affinity for mutant rat GABA-A receptor alpha-6-(his,thr,gly,val)beta2ga...	7799410
Unchecked	IC50	=	2.5	nM	8.6	Displacement of [3H]-flumazenil from benzodiazepine receptor in Sprague-Dawley r...	25564376
GABA-A receptor; anion channel	Ki	=	2.9	nM	8.54	In vitro binding affinity against benzodiazepine receptor using [3H]diazepam as ...	2993620
GABA-A receptor; anion channel	Ki	=	2.9	nM	8.54	Inhibition of [3H]diazepam binding to GABA-A central benzodiazepine receptor of ...	2836588
Unchecked	IC50	=	2.857	nM	8.54	Displacement of [3H]flumazenil from GABAA/BZD receptor in Sprague-Dawley rat cor...	24530225
GABA-A receptor; anion channel	IC50	=	4.0	nM	8.4	Displacement of [3H]diazepam from GABA-A Benzodiazepine receptor of rat forebrai...	1846920
GABA-A receptor; anion channel	IC50	=	4.2	nM	8.38	Inhibition of GABA-A receptor (unknown origin)	34607244
GABA-A receptor; anion channel	IC50	=	4.4	nM	8.36	Displacement of [3H]flunitrazepam from GABA-A Benzodiazepine receptors in rat fo...	1680197
GABA-A receptor; anion channel	IC50	=	4.9	nM	8.31	In vitro affinity for BZD site on GABA-A receptor from rat cerebral cortex using...	12161138
GABA-A receptor; anion channel	IC50	=	4.9	nM	8.31	In vitro inhibitory against Gamma-aminobutyric acid A receptor from rat cerebral...	10386933
GABA-A receptor; anion channel	Ki	=	4.9	nM	8.31	Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor of rat cor...	8917654
GABA-A receptor; anion channel	Ki	=	4.9	nM	8.31	Inhibition of [3H]flunitrazepam binding to GABA-A receptor of rat cortical membr...	8568803
GABA-A receptor; anion channel	Ki	=	4.9	nM	8.31	Binding affinity against benzodiazepine receptor (BzR) in rat cortical membranes...	8809170
GABA-A receptor; anion channel	Ki	=	4.9	nM	8.31	Displacement of [3H]flunitrazepam from GABA-A benzodiazepine receptor of rat cor...	10197957
GABA-A receptor; anion channel	Ki	=	5.0	nM	8.3	Displacement of [3H]diazepam from rat cerebral cortex benzodiazepine receptor	8709114
GABA-A receptor; anion channel	Ki	=	5.0	nM	8.3	In vitro inhibition of [3H]diazepam binding to benzodiazepine receptor in rat ce...	6127411

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1387
-	10.6019/CHEMBL3885881	Rattus norvegicus	430
12477354	10.1021/jm020944u	Mus musculus	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
10377227	10.1021/jm981126y	Mus musculus	18
15787439	10.1021/np049695y	Mus musculus	17
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
6121916	10.1021/jm00346a002	Rattus norvegicus	13
1977910	10.1021/jm00173a012	Rattus norvegicus	12
31534657	10.1039/C9MD00187E	Mus musculus	11
31483	10.1021/jm00210a022	Mus musculus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
22543233	10.1016/j.bmc.2012.04.011	Mus musculus	11
42799	10.1021/jm00197a021	Mus musculus	10
34039	10.1021/jm00187a001	Mus musculus	10
1680197	10.1021/jm00113a032	Rattus norvegicus	10
9511	10.1021/jm00230a016	Mus musculus	9
6103959	10.1021/jm00178a010	Mus musculus	9
19679379	10.1016/j.ejmech.2009.07.014	Mus musculus	9
6103958	10.1021/jm00178a009	Mus musculus	9

Data from ChEMBL 36 via Core Engine