Compound Detail

CHEMBL1112

ARIPIPRAZOLE

💊 Approved Drug

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💊 Approved Drug

O=C1CCc2ccc(OCCCCN3CCN(c4cccc(Cl)c4Cl)CC3)cc2N1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1112
Name	ARIPIPRAZOLE
Phase	Approved
Structure Type	MOL
InChI Key	CEUORZQYGODEFX-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Abilify Abilify asimtufii Abilify maintena Abilify maintena kit Abilify mycite Abilify mycite kit Aripiprazol Aripiprazole Aripiprazole accord Aripiprazole mylan pharma (previously aripiprazole pharmathen) Aripiprazole sandoz Aripiprazole zentiva +5 more

Targets

309

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

448.4

MW (Da)

4.86

ALogP

HBA

HBD

44.8

PSA (Å²)

0.61

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2002
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-prazole
USAN Year	1997

Extended Properties

Molecular Formula	C23H27Cl2N3O2
MW	448.39
Aromatic Rings	2
Heavy Atoms	30
NP-Likeness	-1.16

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Dopamine D2 receptor partial agonist	PARTIAL AGONIST	D(2) dopamine receptor	✓	✓
Serotonin 1a (5-HT1a) receptor partial agonist	PARTIAL AGONIST	5-hydroxytryptamine receptor 1A	✓	✓
Serotonin 2a (5-HT2a) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2A	✓	✓

Indications

Aggression Autistic Disorder Bipolar Disorder Bipolar Disorder Depressive Disorder Depressive Disorder Depressive Disorder, Major Psychomotor Agitation Psychotic Disorders Psychotic Disorders Schizophrenia Tourette Syndrome Alcoholism Alzheimer Disease Anorexia Nervosa Anxiety Child Development Disorders, Pervasive Child Development Disorders, Pervasive Dementia Depression, Postpartum

ATC Classification

N05AX12

aripiprazole

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning

psychiatric toxicity

Country: United States

Black Box Warning

General Warning

Country: United States

Activity Summary

Ki 233 meas. best 9.7

EC50 39 meas. best 9.0

IC50 37 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL217	Ki	9.7	8.8274	0.2	39
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	9.44	8.976	0.4	5
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	9.4	8.4	0.4	4
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.1	7.9783	0.8	30
D(2) dopamine receptor CHEMBL339	Ki	9.1	8.53	0.8	3
D(3) dopamine receptor CHEMBL234	Ki	9.1	8.3409	0.8	23
D(1A) dopamine receptor CHEMBL265	Ki	9.1	7.405	0.8	2
Unchecked CHEMBL612545	Ki	9.0	7.6175	1.0	12
D(2) dopamine receptor CHEMBL217	IC50	9.0	7.9638	1.0	8
D(2) dopamine receptor CHEMBL217	EC50	9.0	7.5936	1.0	28
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	8.77	8.0784	1.7	19
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	8.47	8.47	3.4	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	8.15	8.0475	7.0	4
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.05	7.5467	8.9	3
Alpha-1A adrenergic receptor CHEMBL229	Ki	8.05	7.5433	8.9	3
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	8.0	7.6622	10.0	9
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	7.94	7.94	11.5	1
5-hydroxytryptamine receptor 2C CHEMBL324	Ki	7.74	7.43	18.2	2
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.74	7.0355	18.2	11
D(3) dopamine receptor CHEMBL234	EC50	7.71	7.705	19.5	4
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	7.62	6.518	24.0	5
Histamine H1 receptor CHEMBL231	Ki	7.6	7.3783	25.1	6
5-hydroxytryptamine receptor 2C CHEMBL324	IC50	7.59	7.59	25.7	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	7.5	6.5067	31.6	6
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.42	7.21	37.9	2
D(3) dopamine receptor CHEMBL3138	IC50	7.42	7.42	37.9	1
Unchecked CHEMBL612545	EC50	7.41	7.41	38.9	2
D(4) dopamine receptor CHEMBL219	Ki	7.36	6.892	44.0	15
Histamine H1 receptor CHEMBL3943	Ki	7.31	7.155	48.9	2
Adrenergic receptor alpha-1 CHEMBL2094251	Ki	7.24	7.24	57.0	1
D(3) dopamine receptor CHEMBL234	IC50	7.09	7.09	81.3	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.05	6.6733	89.0	6
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	7.05	7.05	89.4	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	7.0	7.0	100.0	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.0	7.0	100.0	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	7.0	7.0	100.0	1
Alpha-1A adrenergic receptor CHEMBL229	IC50	6.77	6.77	170.0	3
D(1A) dopamine receptor CHEMBL2056	Ki	6.51	6.2463	310.0	8
Histamine H1 receptor CHEMBL231	IC50	6.38	6.38	420.0	3
Serotonin 3 (5-HT3) receptor CHEMBL2094132	Ki	6.3	6.3	501.2	1
D(4) dopamine receptor CHEMBL3361	Ki	6.29	6.29	510.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	6.22	6.0667	598.0	3
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.2	5.824	631.0	5
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	6.11	6.11	780.0	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	6.0	6.0	1000.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.0	6.0	1000.0	1
5-hydroxytryptamine receptor 3A CHEMBL1899	Ki	6.0	6.0	1000.0	1
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.0	6.0	1000.0	1
D(1B) dopamine receptor CHEMBL1850	Ki	5.98	5.86	1051.0	3
Sodium-dependent serotonin transporter CHEMBL313	Ki	5.97	5.97	1080.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	31.7	mL.min-1.kg-1	Homo sapiens
CL	0.83	mL.min-1.kg-1	Homo sapiens
CL	0.8	mL.min-1.kg-1	Homo sapiens
CL	12.52	mL.min-1.kg-1	Mus musculus
CL	7.02	mL.min-1.kg-1	Rattus norvegicus
CL	7.02	mL.min-1.kg-1	Rattus norvegicus
F	87.0	%	Homo sapiens
F	100.0	%	Homo sapiens
F	87.0	%	Homo sapiens
F	87.0	%	Homo sapiens
Fu	0.01	-	Homo sapiens
Fu	0.002	-	Homo sapiens
Fu	0.001	-	Macaca fascicularis
Fu	0.001	-	Canis lupus familiaris
Fu	0.001	-	Cavia porcellus
Fu	0.001	-	Mus musculus
Fu	0.001	-	Rattus norvegicus
Fu	0.001	-	Rattus norvegicus
Fu	0.001	-	Mus musculus
Fu	0.002	-	Mus musculus
Fu	0.001	-	Rattus norvegicus
Fu	0.001	-	Rattus norvegicus
MRT	98.0	hr	Homo sapiens
T1/2	75.0	hr	Homo sapiens
T1/2	75.0	hr	Homo sapiens
T1/2	4.4	hr	Mus musculus
T1/2	0.08167	hr	Homo sapiens
T1/2	0.32	hr	Mus musculus
T1/2	0.8507	hr	Homo sapiens
Tmax	1.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]raclopride from human D2 dopamine receptor expressed in CHO ...	23237836
D(2) dopamine receptor	Ki	=	0.3	nM	9.52	Modulation of human D2L receptor	35176563
D(2) dopamine receptor	Ki	=	0.34	nM	9.47	Displacement of [3H]-raclopride from human D2L receptor expressed in HEK293 cell...	31586817
D(2) dopamine receptor	Ki	=	0.34	nM	9.47	Partial agonist activity at human D2 receptor assessed as inhibition constant	34110150
D(2) dopamine receptor	Ki	=	0.343	nM	9.46	Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ...	25826710
5-hydroxytryptamine receptor 2B	Ki	=	0.36	nM	9.44	Displacement of [3H]-LSD from human 5-HT2B receptor assessed as inhibition const...	37584406
5-hydroxytryptamine receptor 2B	Ki	=	0.36	nM	9.44	Displacement of [3H]LSD from human 5-HT2B receptor expressed in cell membranes a...	27312422
D(2) dopamine receptor	Ki	=	0.38	nM	9.42	Displacement of [3H]spiperone from human D2SR expressed in CHO cell membranes	28870802
D(2) dopamine receptor	Ki	=	0.38	nM	9.42	Displacement of [3H]spiperone from human D2SR expressed in CHO cell membranes by...	28489379
5-hydroxytryptamine receptor 1A	Ki	=	0.4	nM	9.4	Displacement of [3H]-8-OH-DPAT from 5HT1A receptor in Wistar rat hippocampus hom...	20153652
D(2) dopamine receptor	Ki	=	0.45	nM	9.35	Displacement of [3H]spiperone from human Dopamine D2S receptor expressed in CHO ...	28248104
D(2) dopamine receptor	Ki	=	0.45	nM	9.35	Displacement of [3H]Spiperone from human dopamine D2 short receptor expressed in...	24831693
D(2) dopamine receptor	Ki	=	0.48	nM	9.32	Displacement of [3H]-(R)-(+)-7-OH-DPAT from human dopamine D2 receptor expressed...	28300398
D(2) dopamine receptor	Ki	=	0.48	nM	9.32	Displacement of [3H]spiperone from human dopamine D2L receptor expressed in CHO ...	26299826
D(2) dopamine receptor	Ki	=	0.52	nM	9.28	Displacement of [3H]spiperone from human D2LR expressed in CHO cell membranes	28870802
D(2) dopamine receptor	Ki	=	0.52	nM	9.28	Displacement of [3H]spiperone from human D2LR expressed in CHO cell membranes by...	28489379
D(2) dopamine receptor	Ki	=	0.53	nM	9.28	Displacement of [3H]spiperone from human Dopamine D2L receptor expressed in CHO ...	28248104
D(2) dopamine receptor	Ki	=	0.54	nM	9.27	Displacement of [3H]Spiperone from human dopamine D2 long receptor expressed in ...	24831693
D(2) dopamine receptor	Ki	=	0.687	nM	9.16	Displacement of [3H]N-methylspiperone from human D2L receptor expressed in HEK29...	34636551
5-hydroxytryptamine receptor 2A	Ki	=	0.8	nM	9.1	Binding affinity to 5-HT2A	21823597

Literature References

PubMed	DOI	Target Context	# Activities
28248104	10.1021/acs.jmedchem.6b01857	D(2) dopamine receptor	31
-	10.5281/zenodo.13943903	ADMET	29
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
28408223	10.1016/j.bmcl.2017.03.084	D(2) dopamine receptor	9
34110150	10.1021/acs.jmedchem.1c00704	D(2) dopamine receptor	9
25557493	10.1016/j.ejmech.2014.12.045	Rattus norvegicus	9
28300398	10.1021/acs.jmedchem.6b01875	D(2) dopamine receptor	9
24831693	10.1021/jm5004039	D(2) dopamine receptor	9
28489379	10.1021/acs.jmedchem.7b00363	D(2) dopamine receptor	8
28763213	10.1021/acs.jmedchem.7b00839	Mus musculus	8
22112383	10.1124/dmd.111.043083	ADMET	8
34797051	10.1021/acs.jmedchem.1c01327	D(2) dopamine receptor	8
28248104	10.1021/acs.jmedchem.6b01857	Rattus norvegicus	7
24827597	10.1021/jm500457x	D(2) dopamine receptor	7
25936259	10.1016/j.bmc.2015.04.026	Mus musculus	6
22112383	10.1124/dmd.111.043083	Plasma	6
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
26299826	10.1016/j.bmc.2015.07.050	D(2) dopamine receptor	6
23279866	10.1016/j.ejmech.2012.11.042	Mus musculus	6
29439902	10.1016/j.bmcl.2018.02.003	ADMET	6

Data from ChEMBL 36 via Core Engine