Compound Detail

CHEMBL661

ALPRAZOLAM

💊 Approved Drug

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💊 Approved Drug

Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL661
Name	ALPRAZOLAM
Phase	Approved
Structure Type	MOL
InChI Key	VREFGVBLTWBCJP-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Alprazolam Alprazolam civ Niravam NSC-760140 U 31,889 U-31,889 U-31889 Xanax Xanax xr

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

308.8

MW (Da)

3.58

ALogP

HBA

HBD

43.1

PSA (Å²)

0.69

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1981
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Year

1973

Extended Properties

Molecular Formula	C17H13ClN4
MW	308.77
Aromatic Rings	3
Heavy Atoms	22
NP-Likeness	-0.84

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 Anxiety Disorders Panic Disorder Dementia Depressive Disorder Schizophrenia Seizures Dental Anxiety Epilepsy Stress Disorders, Post-Traumatic Asthma Diabetes Mellitus, Type 1 Migraine Disorders Phobia, Social Substance-Related Disorders

ATC Classification

N05BA12

alprazolam

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 6 meas. best 9.22

IC50 5 meas. best 7.78

EC50 4 meas. best 8.0

Kd 1 meas. best 5.61

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
GABA A receptor alpha-2/beta-2/gamma-2 CHEMBL2111413	Ki	9.22	9.22	0.6	1
GABA-A receptor; alpha-1/beta-2/gamma-2 CHEMBL2095172	Ki	9.1	9.1	0.8	1
GABA A receptor alpha-3/beta-2/gamma-2 CHEMBL2111339	Ki	8.85	8.85	1.4	1
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2 CHEMBL4523641	Ki	8.82	8.82	1.5	1
GABA-A receptor; anion channel CHEMBL1907607	Ki	8.48	8.48	3.3	1
Gamma-aminobutyric acid receptor subunit alpha-5 CHEMBL5112	EC50	8.0	8.0	10.0	1
Gamma-aminobutyric acid receptor subunit alpha-2 CHEMBL4956	EC50	7.92	7.92	12.0	1
Unchecked CHEMBL612545	Ki	7.87	7.87	13.5	1
Unchecked CHEMBL612545	IC50	7.78	7.78	16.6	1
Gamma-aminobutyric acid receptor subunit alpha-1 CHEMBL1962	EC50	7.43	7.43	37.0	1
Gamma-aminobutyric acid receptor subunit alpha-3 CHEMBL3026	EC50	7.16	7.16	69.0	1
Bromodomain-containing protein 4 CHEMBL1163125	Kd	5.61	5.61	2460.0	1
Platelet-activating factor receptor CHEMBL5136	IC50	4.66	4.66	22000.0	1
Oryctolagus cuniculus CHEMBL374	IC50	4.38	4.38	41200.0	2
Cholecystokinin receptor type A CHEMBL2871	IC50	4.19	4.19	64000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	0.74	mL.min-1.kg-1	Homo sapiens
CL	0.6	mL.min-1.kg-1	Homo sapiens
CL	0.74	mL.min-1.kg-1	Homo sapiens
CL	0.74	mL.min-1.kg-1	Homo sapiens
CL	3.98	uL.min-1.(10^6cells)-1	Homo sapiens
CL	42.66	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	0.9	mL.min-1.kg-1	Homo sapiens
CL	2.13	mL.min-1.kg-1	Homo sapiens
Cmax	25.91	nM	Homo sapiens
F	49.0	%	Homo sapiens
Fu	0.29	-	-
Fu	0.881	-	-
Fu	0.29	-	Homo sapiens
Fu	0.29	-	Homo sapiens
Fu	0.29	-	Homo sapiens
Fu	1.0	-	Homo sapiens
Fu	0.16	-	Rattus norvegicus
MRT	18.0	hr	Homo sapiens
T1/2	12.0	hr	Homo sapiens
T1/2	17.1	hr	Homo sapiens
T1/2	7.7	hr	Homo sapiens
T1/2	21.8	hr	Homo sapiens
T1/2	10.6	hr	Homo sapiens
T1/2	16.3	hr	Homo sapiens
T1/2	11.0	hr	Homo sapiens
T1/2	11.4	hr	Homo sapiens
T1/2	19.7	hr	Homo sapiens
T1/2	11.2	hr	Homo sapiens
T1/2	6.3	hr	Homo sapiens
T1/2	4.3	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
GABA A receptor alpha-2/beta-2/gamma-2	Ki	=	0.6	nM	9.22	Displacement of [3H]flunitrazepam from human recombinant alpha2beta2gamma2 GABAA...	35218882
GABA-A receptor; alpha-1/beta-2/gamma-2	Ki	=	0.8	nM	9.1	Displacement of [3H]flunitrazepam from human recombinant alpha1beta2gamma2 GABAA...	35218882
GABA A receptor alpha-3/beta-2/gamma-2	Ki	=	1.4	nM	8.85	Displacement of [3H]flunitrazepam from human recombinant alpha3beta2gamma2 GABAA...	35218882
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2	Ki	=	1.5	nM	8.82	Displacement of [3H]flunitrazepam from human recombinant alpha5beta2gamma2 GABAA...	35218882
GABA-A receptor; anion channel	Ki	=	3.3	nM	8.48	Binding affinity was determined by displacement of [3H]flumazenil from rat corte...	12408715
Gamma-aminobutyric acid receptor subunit alpha-5	EC50	=	10.0	nM	8.0	Effective concentration against Gamma-aminobutyric acid A receptor, alpha 5	12408715
Gamma-aminobutyric acid receptor subunit alpha-2	EC50	=	12.0	nM	7.92	Effective concentration against gamma-aminobutyric acid (GABA) A receptor, alpha...	12408715
Unchecked	Ki	=	13.5	nM	7.87	DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun...	-
Unchecked	IC50	=	16.6	nM	7.78	DRUGMATRIX: GABAA, Flunitrazepam, Central radioligand binding (ligand: [3H] Flun...	-
Gamma-aminobutyric acid receptor subunit alpha-1	EC50	=	37.0	nM	7.43	Effective concentration against gamma-aminobutyric acid (GABA) A receptor, alpha...	12408715
Gamma-aminobutyric acid receptor subunit alpha-3	EC50	=	69.0	nM	7.16	Effective concentration against gamma-aminobutyric acid (GABA) A receptor, alpha...	12408715
Bromodomain-containing protein 4	Kd	=	2460.0	nM	5.61	Binding affinity to BRD4-BD1 by isothermal titration calorimetry	22137933
Platelet-activating factor receptor	IC50	=	22000.0	nM	4.66	Inhibition of PAF-induced platelet aggregation in rabbit platelet rich plasma	8496938
Oryctolagus cuniculus	IC50	=	41200.0	nM	4.38	Concentration required to inhibit PAF (5*10e-8 M) induced platelet aggregation i...	1336052
Oryctolagus cuniculus	IC50	=	41200.0	nM	4.38	Concentration needed to inhibit PAF-induced platelet aggregation in rabbit PRP b...	1578493
Cholecystokinin receptor type A	IC50	=	64000.0	nM	4.19	Displacement of [125I]CCK from Cholecystokinin receptor of rat pancreas	3336017

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	301
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
31483	10.1021/jm00210a022	Mus musculus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
42799	10.1021/jm00197a021	Mus musculus	10
9511	10.1021/jm00230a016	Mus musculus	9
20070106	10.1021/jm901371v	Homo sapiens	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
6105215	10.1021/jm00182a012	Mus musculus	7
7154007	10.1021/jm00354a015	Mus musculus	6
6104733	10.1021/jm00180a012	Mus musculus	5
12061889	10.1021/jm0200409	ADMET	5
34908407	10.1021/acs.jmedchem.1c00290	Unchecked	4
36719862	10.1021/acs.jmedchem.2c01886	ADMET	4
22137933	10.1016/j.bmc.2011.10.080	Bromodomain-containing protein 4	4
18426954	10.1124/dmd.108.020479	ADMET	4
12824036	10.1016/s0960-894x(03)00403-7	Mus musculus	4
21149540	10.1124/dmd.110.035998	Brain	3
592339	10.1021/jm00222a035	Mus musculus	3

Data from ChEMBL 36 via Core Engine