Compound Detail

CHEMBL655

MIDAZOLAM

💊 Approved Drug

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💊 Approved Drug

Cc1ncc2n1-c1ccc(Cl)cc1C(c1ccccc1F)=NC2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL655
Name	MIDAZOLAM
Phase	Approved
Structure Type	MOL
InChI Key	DDLIGBOFAVUZHB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Midazolam Midazolam civ Midazolam in 0.8% sodium chloride Midazolam in 0.9% sodium chloride Nayzilam USL-261 USL261

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

325.8

MW (Da)

4.32

ALogP

HBA

HBD

30.2

PSA (Å²)

0.65

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1985
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning

USAN Year

1978

Extended Properties

Molecular Formula	C18H13ClFN3
MW	325.77
Aromatic Rings	3
Heavy Atoms	23
NP-Likeness	-0.60

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 Status Epilepticus Anxiety Brain Injuries Breech Presentation Delirium Dementia Dental Anxiety Depressive Disorder Fluoride Poisoning Fractures, Bone Hemorrhage Hypertension Infertility Liver Cirrhosis Lung Diseases Multiple Sclerosis, Relapsing-Remitting Pain Postoperative Nausea and Vomiting Respiratory Insufficiency

ATC Classification

N05CD08

midazolam

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning

General Warning

Country: United States

Activity Summary

IC50 11 meas. best 7.33

Ki 4 meas. best 8.7

EC50 1 meas. best 6.84

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
GABA-A receptor; anion channel CHEMBL1907607	Ki	8.7	8.7	2.0	1
Translocator protein CHEMBL4552	Ki	8.7	8.7	2.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	7.33	6.8483	47.0	6
Unchecked CHEMBL612545	EC50	6.84	6.84	143.0	1
Cytochrome P450 3A4 CHEMBL340	Ki	5.61	5.61	2470.0	1
Solute carrier family 22 member 1 CHEMBL5685	Ki	5.43	5.43	3700.0	1
ATP-dependent translocase ABCB1 CHEMBL3467	IC50	4.48	4.48	33000.0	2
Bile salt export pump CHEMBL6020	IC50	4.38	4.38	41700.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	5516.67	ng.hr.mL-1	Mus musculus
AUC	228.33	ng.hr.mL-1	Mus musculus
AUC	5833.33	ng.hr.mL-1	Mus musculus
AUC	278.33	ng.hr.mL-1	Mus musculus
AUC	2100.0	ng.hr.mL-1	Mus musculus
AUC	125.0	ng.hr.mL-1	Mus musculus
AUC	2250.0	ng.hr.mL-1	Mus musculus
AUC	145.0	ng.hr.mL-1	Mus musculus
AUC	49.8	ng.hr.mL-1	Homo sapiens
AUC	42.5	ng.hr.mL-1	Homo sapiens
AUC	54.3	ng.hr.mL-1	Homo sapiens
AUC	47.3	ng.hr.mL-1	Homo sapiens
AUC	40.3	ng.hr.mL-1	Homo sapiens
AUC	51.5	ng.hr.mL-1	Homo sapiens
AUC	48.4	ng.hr.mL-1	Homo sapiens
AUC	48.4	ng.hr.mL-1	Homo sapiens
AUC	59.9	ng.hr.mL-1	Homo sapiens
AUC	120.21	ng.hr.mL-1	Homo sapiens
AUC	125.35	ng.hr.mL-1	Mus musculus
CL	130.0	mL.min-1.kg-1	Rattus norvegicus
CL	-	mL.min-1.kg-1	Canis lupus familiaris
CL	11.0	mL.min-1.kg-1	Homo sapiens
CL	554.0	mL.min-1.g-1	Homo sapiens
CL	6.6	mL.min-1.kg-1	Homo sapiens
CL	5.3	mL.min-1.kg-1	Homo sapiens
CL	5.3	mL.min-1.kg-1	Homo sapiens
CL	5.3	mL.min-1.kg-1	Homo sapiens
CL	67.0	mL.min-1.kg-1	Rattus norvegicus
CL	5.3	mL.min-1.kg-1	Homo sapiens
CL	6.6	mL.min-1.kg-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Translocator protein	Ki	=	2.0	nM	8.7	Binding affinity against rat benzodiazepine (BZD) receptor	12372538
GABA-A receptor; anion channel	Ki	=	2.0	nM	8.7	Binding affinity to rat benzodiazepine receptor	12372537
Cytochrome P450 3A4	IC50	=	47.0	nM	7.33	Inhibition of CYP3A4 (unknown origin)	38996652
Cytochrome P450 3A4	IC50	=	61.8	nM	7.21	Inhibition of CYP3A4M (unknown origin)	35797898
Cytochrome P450 3A4	IC50	=	66.2	nM	7.18	Inhibition of CYP3A4M in human liver microsomes incubated for 15 to 40 mins in p...	35679690
Cytochrome P450 3A4	IC50	=	66.0	nM	7.18	Inhibition of CYP3A4M in human liver microsomes using midazolam as substrate mea...	36577220
Cytochrome P450 3A4	IC50	=	80.0	nM	7.1	Inhibition of CYP3A4M (unknown origin)	36442370
Unchecked	EC50	=	143.0	nM	6.84	Allosteric modulation of gamma-aminobutyric acid receptor A alpha1beta2gamma2S e...	21793559
Cytochrome P450 3A4	Ki	=	2470.0	nM	5.61	Inhibition of human recombinant CYP3A4 in liver microsomes by mechanism based in...	25369539
Solute carrier family 22 member 1	Ki	=	3700.0	nM	5.43	TP_TRANSPORTER: inhibition of TEA uptake in OCT1-expressing HeLa cells	9655880
Cytochrome P450 3A4	IC50	=	8100.0	nM	5.09	Inhibition of human cytochrome P450 3A4	12699389
ATP-dependent translocase ABCB1	IC50	=	33000.0	nM	4.48	Inhibition of P-glycoprotein, mouse L-mdr1b expressed in LLC-PK1 epithelial cell...	12699389
ATP-dependent translocase ABCB1	IC50	=	33000.0	nM	4.48	TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1b-expressing LLC-PK1 cell...	12699389
Bile salt export pump	IC50	=	41700.0	nM	4.38	Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves...	20829430
Bile salt export pump	IC50	=	41700.0	nM	4.38	Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ...	24799086
Bile salt export pump	IC50	=	41740.0	nM	4.38	Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as...	23956101

Literature References

PubMed	DOI	Target Context	# Activities
23086197	10.1124/dmd.112.048991	Mus musculus	20
23118326	10.1124/dmd.112.047662	Homo sapiens	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
28686445	10.1021/acs.jmedchem.7b00523	Liver	12
38640868	10.1016/j.ejmech.2024.116399	ADMET	10
12699389	10.1021/jm021012t	ATP-dependent translocase ABCB1	10
34962793	10.1021/acs.jmedchem.1c01864	ADMET	10
31679973	10.1016/j.bmcl.2019.126712	ADMET	10
32447197	10.1016/j.ejmech.2020.112424	ADMET	8
16621936	10.1124/dmd.105.006619	ADMET	8
20070106	10.1021/jm901371v	Homo sapiens	8
30268701	10.1016/j.bmcl.2018.09.025	ADMET	8
11602674	-	ATP-dependent translocase ABCB1	6
22942316	10.1124/dmd.112.047373	Liver microsome	6
38364599	10.1016/j.bmc.2024.117609	ADMET	6
21098647	10.1124/dmd.110.036988	ADMET	5
-	10.6019/CHEMBL3301361	ADMET	5
38199331	10.1016/j.bmcl.2024.129615	ADMET	5
30508668	10.1016/j.ejmech.2018.11.063	ADMET	4

Data from ChEMBL 36 via Core Engine