Compound Detail

CHEMBL54

HALOPERIDOL

💊 Approved Drug

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💊 Approved Drug

O=C(CCCN1CCC(O)(c2ccc(Cl)cc2)CC1)c1ccc(F)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL54
Name	HALOPERIDOL
Phase	Approved
Structure Type	MOL
InChI Key	LNEPOXFFQSENCJ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Dolpin Dozic Fortunan Haldol Haldol solutab Haloperidol Haloperidol component of vesalium Haloperidol decanoate impurity, haloperidol- Kentace Keselen MCN-JR-1625 NSC-170973 +3 more

100

Targets

1,071

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

375.9

MW (Da)

4.43

ALogP

HBA

HBD

40.5

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning

USAN Year

1965

Extended Properties

Molecular Formula	C21H23ClFNO2
MW	375.87
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	-0.94

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin 2a (5-HT2a) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2A	✓	✓
D2-like dopamine receptor inverse agonist	INVERSE AGONIST	D2-like dopamine receptor	✓	✓

Indications

Conduct Disorder Psychotic Disorders Psychotic Disorders Psychotic Disorders Schizophrenia Tics Tourette Syndrome Alzheimer Disease Anxiety Bipolar Disorder Delirium Dementia Depressive Disorder Emergence Delirium Nausea Postoperative Complications Psychomotor Agitation Aggression Amphetamine-Related Disorders Mood Disorders

ATC Classification

N05AD01

haloperidol

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

Black Box Warning

respiratory toxicity

Country: United States

Activity Summary

Ki 828 meas. best 10.0

IC50 230 meas. best 10.22

Kd 8 meas. best 9.31

EC50 5 meas. best 8.56

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(3) dopamine receptor CHEMBL234	IC50	10.22	8.7175	0.1	8
D(2) dopamine receptor CHEMBL339	IC50	10.12	8.1335	0.1	26
Unchecked CHEMBL612545	Ki	10.0	7.417	0.1	115
D(2) dopamine receptor CHEMBL217	Ki	9.92	8.7423	0.1	103
D(2) dopamine receptor CHEMBL217	IC50	9.8	8.383	0.2	10
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	9.7	8.5424	0.2	55
D(2) dopamine receptor CHEMBL339	Ki	9.7	8.8003	0.2	59
Dopamine receptor CHEMBL2093868	IC50	9.55	8.2833	0.3	9
D(2) dopamine receptor CHEMBL3998	Ki	9.52	8.79	0.3	3
D(2) dopamine receptor CHEMBL217	Kd	9.31	9.31	0.5	1
C-8 sterol isomerase ERG2 CHEMBL3224	Ki	9.3	9.3	0.5	1
Sigma non-opioid intracellular receptor 1 CHEMBL3602	IC50	9.19	8.5483	0.7	6
D(3) dopamine receptor CHEMBL234	Ki	9.16	8.2302	0.7	53
D(4) dopamine receptor CHEMBL219	Ki	9.13	8.2944	0.7	45
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	9.08	8.3935	0.8	89
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	9.05	8.235	0.9	24
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	9.0	7.9912	1.0	17
D(2) dopamine receptor CHEMBL3998	IC50	8.92	8.22	1.2	2
D(4) dopamine receptor CHEMBL219	IC50	8.89	7.97	1.3	5
Dopamine receptor CHEMBL2096970	IC50	8.74	7.52	1.8	2
Unchecked CHEMBL612545	IC50	8.74	6.399	1.8	30
Dopamine receptor CHEMBL2093868	Ki	8.7	8.7	2.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	8.68	7.9467	2.1	12
Dopamine receptor D2 and D3 CHEMBL2111342	Ki	8.62	8.605	2.4	2
D(3) dopamine receptor CHEMBL234	EC50	8.56	8.56	2.8	1
D(3) dopamine receptor CHEMBL2304406	Ki	8.52	8.52	3.0	1
D(3) dopamine receptor CHEMBL3138	Ki	8.52	7.9536	3.0	14
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	8.38	7.6425	4.2	12
D(2) dopamine receptor CHEMBL5456	Ki	8.32	8.31	4.8	2
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.31	8.31	4.9	1
Dopamine receptor CHEMBL2096905	IC50	8.3	8.3	5.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Ki	8.24	7.98	5.7	2
Sigma 2 receptor CHEMBL613288	Ki	8.22	7.7392	6.0	12
D(1A) dopamine receptor CHEMBL2056	Ki	8.21	7.177	6.2	10
Zinc finger protein 664 CHEMBL4105757	Ki	8.18	8.18	6.6	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	8.15	7.1944	7.0	9
CHO-hD3 CHEMBL614557	IC50	8.06	8.06	8.8	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	8.05	8.05	8.9	1
D(1A) dopamine receptor CHEMBL5067	Ki	8.02	7.2725	9.5	4
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.0	7.2113	10.0	16
D(4) dopamine receptor CHEMBL3361	Ki	8.0	8.0	10.0	1
Rattus norvegicus CHEMBL376	IC50	8.0	8.0	10.0	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	7.96	7.94	11.0	2
Glutamate receptor ionotropic, NMDA 2B CHEMBL3442	Ki	7.89	7.89	13.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2095200	Ki	7.8	7.6567	16.0	3
Sigma intracellular receptor 2 CHEMBL4105907	Ki	7.8	7.44	16.0	9
D(4) dopamine receptor CHEMBL219	EC50	7.77	7.77	17.0	1
Sigma 2 receptor CHEMBL613288	IC50	7.77	7.3633	17.0	3
Alpha-1A adrenergic receptor CHEMBL319	Kd	7.76	7.76	17.4	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	7.75	7.0133	18.0	9

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	266.4	-	Chlorocebus sabaeus
CL	7.8	mL.min-1.kg-1	Homo sapiens
CL	7.7	mL.min-1.kg-1	Homo sapiens
CL	7.8	mL.min-1.kg-1	Homo sapiens
CL	86.2	mL.min-1.kg-1	Rattus norvegicus
CL	7.8	mL.min-1.kg-1	Macaca
CL	7.8	mL.min-1.kg-1	Homo sapiens
CL	11.8	mL.min-1.kg-1	Homo sapiens
CL	32.9	mL.min-1.kg-1	Canis lupus familiaris
CL	20000.0	mL.min-1.g-1	Homo sapiens
CL	21000.0	mL.min-1.g-1	Rattus norvegicus
CL	8.0	mL.min-1.g-1	Homo sapiens
CL	14.24	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	14.0	mL.min-1.g-1	Homo sapiens
CL	145.0	mL.min-1.g-1	Homo sapiens
CL	16.0	mL.min-1.g-1	Homo sapiens
CL	6.0	mL.min-1.g-1	Homo sapiens
CL	30.0	mL.min-1.g-1	Homo sapiens
CL	51.0	mL.min-1.g-1	Homo sapiens
CL	1.8	mL.min-1.g-1	Homo sapiens
CL	1.8	mL.min-1.g-1	Homo sapiens
CL	30.0	mL.min-1.g-1	Homo sapiens
CL	0.038	mL.min-1.g-1	Homo sapiens
CL	0.009	mL.min-1.g-1	Homo sapiens
CL	0.016	mL.min-1.g-1	Homo sapiens
CL	0.023	mL.min-1.g-1	Homo sapiens
CL	550.0	ml/min	Homo sapiens
CL	435.0	ml/min	Homo sapiens
CL	439.0	ml/min	Homo sapiens
F	79.0	%	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(3) dopamine receptor	IC50	=	0.06	nM	10.22	Antagonist activity against D3R in human U2OS cells assessed as inhibition of (+...	25126833
D(2) dopamine receptor	IC50	=	0.075	nM	10.12	In vivo binding affinity against dopamine (D2) receptor in rat caudate-putamen t...	14592497
Unchecked	Ki	=	0.1	nM	10.0	Ratio of Ki for human dopamine D2 receptor to Ki for human dopamine D4 receptor	19155177
D(2) dopamine receptor	Ki	=	0.12	nM	9.92	Antagonist activity at dopamine D2 receptor (unknown origin)	33111525
D(2) dopamine receptor	Ki	=	0.12	nM	9.92	Binding affinity towards human Dopamine receptor D2 using [3H]spiroperidol as ra...	12477356
D(2) dopamine receptor	Ki	=	0.16	nM	9.8	Displacement of [3H]quinpirole from human dopamine D2A receptors expressed in Lt...	10465538
D(2) dopamine receptor	IC50	=	0.16	nM	9.8	Antagonist activity against human D2LR expressed in CHOK1 cells assessed as inhi...	25126833
D(2) dopamine receptor	IC50	=	0.16	nM	9.8	Antagonist activity at recombinant human D2 receptor expressed in CHOK1 cells as...	31021617
D(2) dopamine receptor	Ki	=	0.16	nM	9.8	Displacement of [3H]quinpirole from Dopamine receptor D2	8893836
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Binding towards Dopamine receptor D2 using [3H]spiperone from rat striatal membr...	8230107
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Affinity for Dopamine receptor D2	9871525
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Binding affinity towards dopamine receptor D2 by displacing [3H]spiperone radiol...	1346653
D(2) dopamine receptor	Ki	=	0.2	nM	9.7	Binding affinity was determined against Dopamine receptor D2 using [3H]spiperone	7473547
Sigma non-opioid intracellular receptor 1	Ki	=	0.2	nM	9.7	Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H...	16033255
Sigma non-opioid intracellular receptor 1	Ki	=	0.21	nM	9.68	Displacement of [3H]-(+)-pentazocine from sigma1 in human MDA-MB-468 cell membra...	28385503
D(2) dopamine receptor	Ki	=	0.25	nM	9.6	Displacement of [3H]spiperone from human D2short receptor expressed in CHO cell ...	28666858
D(3) dopamine receptor	IC50	=	0.25	nM	9.6	Antagonist activity at recombinant human D3 receptor expressed in CHOK1 cells as...	31021617
D(2) dopamine receptor	Ki	=	0.263	nM	9.58	Displacement of [3H]N-methylspiperone from human D2L receptor expressed in HEK29...	33548637
Dopamine receptor	IC50	=	0.28	nM	9.55	Ability to inhibit [3H]haloperidol binding to dopamine receptor in rat striatal ...	2866248
D(2) dopamine receptor	Ki	=	0.3	nM	9.52	Evaluated for binding towards Dopamine receptor D2 using [3H]-spiperone as radio...	8230107

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1381
-	10.6019/CHEMBL3885881	Rattus norvegicus	295
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	60
2571727	10.1021/jm00130a003	Mus musculus	26
16472241	10.2174/1570163043334794	Hepatotoxicity	18
7902870	10.1021/jm00076a022	Rattus norvegicus	18
22028316	10.1124/dmd.111.042150	Liver microsome	17
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
3108922	10.1007/bf00216005	Homo sapiens	14
27739690	10.1021/acs.jmedchem.6b01039	Unchecked	12
23444387	10.1124/dmd.113.051177	ADMET	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
-	10.1007/s00044-008-9127-y	Mus musculus	11
1246033	10.1021/jm00223a021	Mus musculus	10
-	10.1007/s00044-011-9786-y	Mus musculus	10
22028316	10.1124/dmd.111.042150	UDP-glucuronosyltransferase 2B7	10
22028316	10.1124/dmd.111.042150	UDP-glucuronosyltransferase 1A9	10
22028316	10.1124/dmd.111.042150	UDP-glucuronosyltransferase 1A4	10
29407591	10.1016/j.ejmech.2018.01.002	Rattus norvegicus	10

Data from ChEMBL 36 via Core Engine