Compound Detail

CHEMBL1423

PIMOZIDE

💊 Approved Drug

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💊 Approved Drug

O=c1[nH]c2ccccc2n1C1CCN(CCCC(c2ccc(F)cc2)c2ccc(F)cc2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1423
Name	PIMOZIDE
Phase	Approved
Structure Type	MOL
InChI Key	YVUQSNJEYSNKRX-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

MCN-JR-6238 NSC-170984 Orap Pimozida Pimozide R 623 R 6238 R-623 R-6238

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

461.6

MW (Da)

5.86

ALogP

HBA

HBD

41.0

PSA (Å²)

0.37

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1984
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

USAN Year

1967

Extended Properties

Molecular Formula	C28H29F2N3O
MW	461.56
Aromatic Rings	4
Heavy Atoms	34
NP-Likeness	-1.03

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin 2a (5-HT2a) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2A	✓	✓
Dopamine receptor antagonist	ANTAGONIST	Dopamine receptor	✓	✓

Indications

Psychotic Disorders Tics Tourette Syndrome Anxiety Dementia Depressive Disorder Schizophrenia Amyotrophic Lateral Sclerosis

ATC Classification

N05AG02

pimozide

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Activity Summary

IC50 50 meas. best 9.4

Ki 10 meas. best 9.3

EC50 6 meas. best 5.77

Kd 2 meas. best 7.54

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dopamine receptor CHEMBL2093868	IC50	9.4	9.36	0.4	2
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	9.3	9.3	0.5	1
D(2) dopamine receptor CHEMBL3998	Ki	9.22	9.22	0.6	1
D(2) dopamine receptor CHEMBL217	Ki	8.85	8.2333	1.4	3
D(3) dopamine receptor CHEMBL234	Ki	8.6	8.6	2.5	1
Serotonin 2 (5-HT2) receptor CHEMBL2095200	IC50	8.57	8.57	2.7	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.52	7.4571	3.0	14
D(2) dopamine receptor CHEMBL217	Kd	7.54	7.54	29.0	1
Voltage-dependent T-type calcium channel subunit alpha-1G CHEMBL4641	Kd	7.4	7.4	40.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	7.38	7.38	42.0	1
Sodium channel alpha subunit CHEMBL2331043	IC50	7.27	7.27	54.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.15	7.15	71.0	1
Voltage-dependent T-type calcium channel subunit alpha-1H CHEMBL1859	IC50	6.8	6.8	157.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	6.79	6.705	162.0	2
Voltage-dependent T-type calcium channel subunit alpha-1G CHEMBL4641	IC50	6.51	6.51	307.0	1
Sodium channel protein type 2 subunit alpha CHEMBL3399	IC50	6.47	6.47	340.0	1
Mu-type opioid receptor CHEMBL233	IC50	6.43	6.43	372.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.23	6.23	588.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	6.1	5.7267	800.0	3
Kappa-type opioid receptor CHEMBL237	IC50	6.0	6.0	990.0	1
Glycine receptor subunit alpha-1 CHEMBL5845	EC50	5.77	5.77	1700.0	1
Potassium channel subfamily K member 2 CHEMBL2321615	IC50	5.75	5.75	1800.0	1
Ubiquitin carboxyl-terminal hydrolase 1 CHEMBL1795087	IC50	5.7	5.7	2000.0	1
Histamine H4 receptor CHEMBL3759	Ki	5.7	5.7	2000.0	1
Ubiquitin carboxyl-terminal hydrolase 1/WD repeat-containing protein 48 CHEMBL3430885	IC50	5.7	5.7	2000.0	1
Unchecked CHEMBL612545	IC50	5.66	5.4767	2171.0	3
Plasmodium falciparum CHEMBL364	IC50	5.6	5.3	2511.9	7
Delta-type opioid receptor CHEMBL236	IC50	5.42	5.42	3760.0	1
ATP-dependent translocase ABCB1 CHEMBL2573	IC50	5.31	5.31	4900.0	2
K562 CHEMBL385	IC50	5.3	5.3	5000.0	1
Unchecked CHEMBL612545	EC50	5.27	5.036	5400.0	5
Cytochrome P450 3A4 CHEMBL340	IC50	5.01	5.01	9700.0	1
HCT-116 CHEMBL394	IC50	5.0	5.0	10000.0	1
SW480 CHEMBL612544	IC50	5.0	5.0	10000.0	1
Solute carrier family 22 member 2 CHEMBL1743122	IC50	4.47	4.47	34200.0	1
SARS-CoV-2 CHEMBL4303835	IC50	4.04	4.04	91201.1	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	189.8	-	Chlorocebus sabaeus
CL	57.0	mL.min-1.g-1	Homo sapiens
F	49.0	%	Homo sapiens
F	50.0	%	Homo sapiens
Fu	0.0016	-	Homo sapiens
Fu	0.0004	-	Canis lupus familiaris
T1/2	0.045	hr	Homo sapiens
T1/2	0.05333	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	2.47	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dopamine receptor	IC50	=	0.4	nM	9.4	Inhibition of [3H]haloperidol binding to dopamine receptors in rat striatal memb...	2859371
Dopamine receptor	IC50	=	0.48	nM	9.32	Inhibition of [3H]haloperidol binding to dopamine receptors in rat striatal memb...	2859371
5-hydroxytryptamine receptor 7	Ki	=	0.5	nM	9.3	Binding affinity towards rat 5-hydroxytryptamine 7 receptor	12825922
D(2) dopamine receptor	Ki	=	0.6	nM	9.22	Binding affinity of compound towards Dopamine receptor D2 using [3H]raclopride (...	9083484
D(2) dopamine receptor	Ki	=	1.4	nM	8.85	Binding affinity to dopamine D2 receptor (unknown origin) assessed as inhibition...	36075145
D(3) dopamine receptor	Ki	=	2.5	nM	8.6	Binding affinity to human dopamine D3 receptor expressed in CHO cells assessed a...	36075145
Serotonin 2 (5-HT2) receptor	IC50	=	2.7	nM	8.57	Antagonist activity at 5-HT2 receptor (unknown origin)	36075145
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	3.02	nM	8.52	Inhibition of human ERG channel in HEK293 cells by voltage-clamp method	18262683
D(2) dopamine receptor	Ki	=	11.7	nM	7.93	Displacement of [3H]methylspiperone from human low affinity Dopamine D2S recepto...	23043306
D(2) dopamine receptor	Ki	=	12.0	nM	7.92	Binding affinity towards Dopamine receptor D2	12747773
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	18.0	nM	7.75	Inhibitory activity against Potassium channel HERG	12747773
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	18.0	nM	7.75	K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv1...	12190308
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	18.0	nM	7.75	Inhibition of K+ channel activity in CHO cells expressing HERG Kv11.1	12729675
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	18.2	nM	7.74	Inhibition of human voltage-gated potassium channel subunit Kv11.1 (ERG K+ chann...	15745831
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	18.2	nM	7.74	Inhibition of human ERG in MCF7 cells	19110341
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	20.0	nM	7.7	Inhibition of hERG K channel	21300721
D(2) dopamine receptor	Kd	=	29.0	nM	7.54	Inhibition of dopamine D2 receptor	20659804
Voltage-dependent T-type calcium channel subunit alpha-1G	Kd	=	40.0	nM	7.4	Inhibition of T-type alpha1G calcium channel	21126876
Voltage-gated inwardly rectifying potassium channel KCNH2	Ki	=	42.0	nM	7.38	Displacement of [3H]Astemizole from hERG expressed in HEK293 cells at 10 uM	16908150
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	50.12	nM	7.3	Inhibitory concentration against potassium channel HERG	15911273

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	71
-	10.6019/CHEMBL4295262	Unchecked	36
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18024584	10.1073/pnas.0709695104	H4	13
19015342	10.1128/aac.00607-08	Listeria monocytogenes	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
12699389	10.1021/jm021012t	ATP-dependent translocase ABCB1	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
25131537	10.1016/j.bmcl.2014.07.069	K562	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23043306	10.1021/jm300975f	Rattus norvegicus	4
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	4
2859371	10.1021/jm50001a013	Dopamine receptor	4
22328583	10.1124/dmd.111.043505	Cytochrome P450 2J2	4

Data from ChEMBL 36 via Core Engine