Compound Detail

CHEMBL71

CHLORPROMAZINE

💊 Approved Drug

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💊 Approved Drug

CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL71
Name	CHLORPROMAZINE
Phase	Approved
Structure Type	MOL
InChI Key	ZPEIMTDSQAKGNT-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Aminazine Chlorpromazine Chlorpromazinum Clorpromazina Elmarin Esmind Fenactil J2.794D Largactilothiazine Megaphen Novomazina NSC-167745 +6 more

101

Targets

303

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

318.9

MW (Da)

4.89

ALogP

HBA

HBD

6.5

PSA (Å²)

0.79

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1957
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula	C17H19ClN2S
MW	318.87
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-1.54

Mechanism of Action

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

Indications

Conduct Disorder Porphyrias Postoperative Nausea and Vomiting Psychotic Disorders Psychotic Disorders Schizophrenia Neonatal Abstinence Syndrome Severe Acute Respiratory Syndrome Delirium Glioblastoma Colonic Neoplasms

ATC Classification

N05AA01

chlorpromazine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Activity Summary

IC50 153 meas. best 9.0

Ki 137 meas. best 9.15

EC50 7 meas. best 5.7

Kd 6 meas. best 6.74

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	9.15	8.7033	0.7	3
D(2) dopamine receptor CHEMBL217	IC50	9.0	8.342	1.0	5
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	8.96	8.308	1.1	5
D(2) dopamine receptor CHEMBL217	Ki	8.92	8.3867	1.2	9
D(2) dopamine receptor CHEMBL339	Ki	8.92	8.396	1.2	10
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.8	8.53	1.6	2
D(3) dopamine receptor CHEMBL234	Ki	8.8	8.2827	1.6	11
Alpha-1D adrenergic receptor CHEMBL223	Ki	8.71	8.71	2.0	1
Histamine H1 receptor CHEMBL231	Ki	8.71	8.54	2.0	2
D(1A) dopamine receptor CHEMBL265	IC50	8.67	8.67	2.1	1
Unchecked CHEMBL612545	Ki	8.57	7.1453	2.7	15
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.56	7.714	2.7	5
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	8.47	8.44	3.4	2
Alpha-1A adrenergic receptor CHEMBL319	Ki	8.46	8.46	3.5	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	8.4	8.4	4.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	8.4	7.544	4.0	5
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.3	8.3	5.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	8.28	8.28	5.2	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	8.07	8.07	8.5	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	8.06	8.06	8.8	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	8.05	8.05	9.0	1
Dopamine receptor CHEMBL2093868	IC50	8.01	7.3555	9.9	11
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.97	7.4733	10.7	6
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.92	7.92	12.0	1
Histamine H1 receptor CHEMBL231	IC50	7.92	7.845	12.0	2
D(3) dopamine receptor CHEMBL234	IC50	7.92	7.92	12.0	1
Dopamine receptor CHEMBL2093868	Ki	7.85	7.85	14.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	7.75	7.75	18.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	7.72	7.72	19.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	7.72	7.72	19.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.7	7.3	20.0	2
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.68	7.24	21.0	2
Sodium-dependent serotonin transporter CHEMBL228	Ki	7.68	7.44	21.0	2
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	7.68	7.68	21.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	7.6	7.6	25.0	1
Dopamine receptor CHEMBL2096970	IC50	7.6	7.0675	25.0	4
D(4) dopamine receptor CHEMBL219	Ki	7.6	7.235	25.1	4
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.58	7.58	26.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	7.51	7.51	31.0	2
Unchecked CHEMBL612545	IC50	7.47	5.521	34.0	20
D(1A) dopamine receptor CHEMBL265	Ki	7.46	7.4033	35.0	3
Sodium-dependent serotonin transporter CHEMBL228	IC50	7.41	7.165	39.0	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.4	7.26	39.8	3
D(2) dopamine receptor CHEMBL339	IC50	7.4	7.4	40.0	2
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.36	7.36	44.0	1
Histamine H1 receptor CHEMBL3943	Ki	7.3	7.3	50.1	1
Rattus norvegicus CHEMBL376	IC50	7.29	7.02	51.0	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.27	7.27	54.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	7.24	7.24	57.0	1
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	7.22	7.22	60.3	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	117.0	mL.min-1.g-1	Homo sapiens
CL	8.6	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	15.8	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	53.0	mL.min-1.kg-1	Canis lupus familiaris
CL	61.0	mL.min-1.kg-1	Rattus norvegicus
CL	4.3	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	24.6	mL.min-1.kg-1	Macaca
CL	14.45	uL.min-1.(10^6cells)-1	Homo sapiens
CL	37.15	mL.min-1.g-1	Homo sapiens
CL	150.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	278.0	mL.min-1.kg-1	Homo sapiens
CL	82.5	uL.min-1.(10^6cells)-1	Homo sapiens
CL	252.2	uL.min-1.(10^6cells)-1	Homo sapiens
CL	14000.0	mL.min-1.kg-1	Homo sapiens
CL	1.0	mL.min-1.kg-1	Homo sapiens
CL	18.3	mL.min-1.kg-1	Homo sapiens
CL	8.6	mL.min-1.kg-1	Homo sapiens
F	49.0	%	Homo sapiens
F	32.0	%	Homo sapiens
Fu	0.03	-	-
Fu	0.001	-	-
Fu	0.03	-	Homo sapiens
Fu	0.056	-	Homo sapiens
Fu	0.056	-	Homo sapiens
Fu	0.003	-	Homo sapiens
Fu	0.002	-	Rattus norvegicus
Fu	0.0022	-	Sus scrofa

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Serotonin 2 (5-HT2) receptor	Ki	=	0.7	nM	9.15	Binding affinity determined in radioreceptor binding assay by using [3H]ketanser...	1346653
D(2) dopamine receptor	IC50	=	1.0	nM	9.0	Antagonist activity against human recombinant dopmaine D2L receptor expressed in...	25557493
D(2) dopamine receptor	IC50	=	1.0	nM	9.0	Antagonist activity at human dopamine D2 receptor expressed in CHOK1 cells asses...	25557493
5-hydroxytryptamine receptor 2A	Ki	=	1.1	nM	8.96	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
D(2) dopamine receptor	Ki	=	1.2	nM	8.92	Displacement of [3H]-N-methylspiperone from human dopamine D2long receptor expre...	23018094
D(2) dopamine receptor	Ki	=	1.2	nM	8.92	Compound was tested for inhibitory activity against the binding of [3H]spiperone...	2887659
Adrenergic receptor alpha-1	Ki	=	1.585	nM	8.8	Displacement of [3H]prazosin from adrenergic alpha1 receptor in rat cerebral cor...	17880057
D(3) dopamine receptor	Ki	=	1.585	nM	8.8	Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO c...	17880057
D(2) dopamine receptor	Ki	=	1.77	nM	8.75	Compound was evaluated for binding affinity towards Dopamine receptor D2 in stri...	1827843
D(2) dopamine receptor	Ki	=	1.8	nM	8.74	Displacement of [3H]-raclopride from recombinant human D2 receptor expressed in ...	30703658
D(2) dopamine receptor	Ki	=	1.8	nM	8.74	Displacement of [3H]-raclopride from human D2 receptor expressed in HEK cells in...	31325785
Alpha-1D adrenergic receptor	Ki	=	1.962	nM	8.71	DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin)	-
Histamine H1 receptor	Ki	=	1.957	nM	8.71	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
D(2) dopamine receptor	Ki	=	2.01	nM	8.7	In vitro binding affinity against Dopamine D2 receptor in rat striatal tissue.	8101877
D(2) dopamine receptor	Ki	=	1.995	nM	8.7	Binding affinity against dopamine D2 receptor	7907148
D(1A) dopamine receptor	IC50	=	2.15	nM	8.67	Binding affinity against Dopamine receptor D1 by using [3H]SCH-23390 as radiolig...	7830274
D(2) dopamine receptor	Ki	=	2.19	nM	8.66	Compound was evaluated for binding affinity towards Dopamine receptor D2 in stri...	1827843
D(2) dopamine receptor	Ki	=	2.344	nM	8.63	Displacement of [3H]-methylspiperone from human D2 receptor transfected in CHO-K...	34436892
Unchecked	Ki	=	2.67	nM	8.57	Displacement of [3H]-N-methylspiperone from dopamine D2-like receptor in pig str...	21862338
5-hydroxytryptamine receptor 2C	Ki	=	2.742	nM	8.56	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1218
-	10.6019/CHEMBL3885881	Rattus norvegicus	458
28964936	10.1016/j.ejmech.2017.09.014	Unchecked	186
2571727	10.1021/jm00130a003	Mus musculus	26
-	10.6019/CHEMBL4295262	Unchecked	24
18694955	10.1128/aac.00661-08	NON-PROTEIN TARGET	19
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
35707966	10.1021/acs.jnatprod.2c00376	ADMET	14
6167716	10.1021/jm00135a006	ADMET	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
22753	10.1021/jm00199a029	Mus musculus	11
24997576	10.1016/j.bmc.2014.06.012	Mycolicibacterium smegmatis	11
42799	10.1021/jm00197a021	Mus musculus	10
2891853	10.1021/jm00396a016	Mus musculus	10
2571727	10.1021/jm00130a003	Rattus norvegicus	9
18765686	10.1128/aac.00197-08	Naegleria fowleri	9
20070106	10.1021/jm901371v	Homo sapiens	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
37336	10.1021/jm00192a013	Mus musculus	8
-	10.1039/C3MD00387F	Mycolicibacterium smegmatis	8

Data from ChEMBL 36 via Core Engine