Compound Detail

CHEMBL908

CHLORPROTHIXENE

💊 Approved Drug

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💊 Approved Drug

CN(C)CC/C=C1/c2ccccc2Sc2ccc(Cl)cc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL908
Name	CHLORPROTHIXENE
Phase	Approved
Structure Type	MOL
InChI Key	WSPOMRSOLSGNFJ-AUWJEWJLSA-N
Therapeutic	✓ Yes

Known Names

Chlorprothixene Clorprotixeno N-714 N-714RO 4-0403 NSC-18720 RO 4-0403 RO-4-0403 RO-40403 Taractan Truxal

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

315.9

MW (Da)

5.19

ALogP

HBA

HBD

3.2

PSA (Å²)

0.65

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Year

1962

Extended Properties

Molecular Formula	C18H18ClNS
MW	315.87
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-0.83

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Dopamine D2 receptor antagonist	ANTAGONIST	D(2) dopamine receptor	✓	✓
Dopamine D3 receptor antagonist	ANTAGONIST	D(3) dopamine receptor	✓	✓
Serotonin 2a (5-HT2a) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2A	✓	✓
Serotonin 2c (5-HT2c) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2C	✓	✓

Indications

Psychotic Disorders Anxiety Dementia Depressive Disorder Schizophrenia

ATC Classification

N05AF03

chlorprothixene

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Activity Summary

IC50 7 meas. best 9.0

Ki 7 meas. best 8.53

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL231	IC50	9.0	7.53	1.0	2
Histamine H1 receptor CHEMBL4701	IC50	8.97	8.97	1.1	1
D(2) dopamine receptor CHEMBL217	Ki	8.53	8.53	3.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	8.52	8.52	3.0	1
Histamine H1 receptor CHEMBL231	Ki	8.43	8.43	3.8	1
D(3) dopamine receptor CHEMBL234	Ki	8.34	8.34	4.6	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	8.25	8.25	5.6	1
D(1B) dopamine receptor CHEMBL1850	Ki	8.05	8.05	9.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	7.75	7.75	18.0	1
Pleiotropic ABC efflux transporter of multiple drugs CHEMBL1697658	IC50	5.29	5.29	5100.0	1
Bile salt export pump CHEMBL6020	IC50	4.56	4.56	27470.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	4.38	4.38	42000.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.11	4.11	77800.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	IC50	=	1.0	nM	9.0	Antagonist activity at H1 receptor in human HeLa cells assessed as inhibition of...	22793499
Histamine H1 receptor	IC50	=	1.072	nM	8.97	Displacement of [3H]mepyramine from histamine H1 receptor in Sprague-Dawley rat ...	22793499
D(2) dopamine receptor	Ki	=	2.96	nM	8.53	Displacement of [3H]spiperone from human dopamine D2 receptor expressed in CHO c...	19091563
5-hydroxytryptamine receptor 6	Ki	=	3.0	nM	8.52	Binding affinity towards human 5-hydroxytryptamine 6 receptor	12825922
Histamine H1 receptor	Ki	=	3.75	nM	8.43	Displacement of [3H]pyrilamine from human histamine H1 receptor expressed in CHO...	19091563
D(3) dopamine receptor	Ki	=	4.56	nM	8.34	Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO c...	19091563
5-hydroxytryptamine receptor 7	Ki	=	5.6	nM	8.25	Binding affinity towards rat 5-hydroxytryptamine 7 receptor	12825922
D(1B) dopamine receptor	Ki	=	9.0	nM	8.05	Displacement of [3H]SCH23390 from human dopamine D5 receptor expressed in HEK ce...	19091563
D(1A) dopamine receptor	Ki	=	18.0	nM	7.75	Displacement of [3H]SCH23390 from human dopamine D1 receptor expressed in HEK ce...	19091563
Histamine H1 receptor	IC50	=	870.96	nM	6.06	Antagonist activity at H1 receptor in human HeLa cells assessed as inhibition of...	22793499
Pleiotropic ABC efflux transporter of multiple drugs	IC50	=	5100.0	nM	5.29	Inhibition of Pdr5p-mediated rhodamine 6G transport in Saccharomyces cerevisiae ...	19188399
Bile salt export pump	IC50	=	27470.0	nM	4.56	Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21...	22961681
Broad substrate specificity ATP-binding cassette transporter ABCG2	IC50	=	42000.0	nM	4.38	Inhibition of human ABCG2 expressed in human SAOS-2 cells mediated mitoxantrone ...	35483322
Solute carrier family 22 member 1	IC50	=	77800.0	nM	4.11	Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT...	18788725

Literature References

PubMed	DOI	Target Context	# Activities
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
6167716	10.1021/jm00135a006	ADMET	4
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	3
37468498	10.1038/s41467-023-40064-9	Androgen receptor	3
22793499	10.1021/jm300671m	Histamine H1 receptor	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
37468498	10.1038/s41467-023-40064-9	Progesterone receptor	3
6167716	10.1021/jm00135a006	Rattus norvegicus	2
37468498	10.1038/s41467-023-40064-9	Estrogen receptor	2
37468498	10.1038/s41467-023-40064-9	Sodium-dependent dopamine transporter	2
37468498	10.1038/s41467-023-40064-9	Sodium-dependent noradrenaline transporter	2
18027916	10.1021/jm070524a	No relevant target	2
37468498	10.1038/s41467-023-40064-9	Sodium-dependent serotonin transporter	2
18788725	10.1021/jm8003152	Solute carrier family 22 member 1	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
37468498	10.1038/s41467-023-40064-9	Peroxisome proliferator-activated receptor gamma	2
-	10.6019/CHEMBL4651402	Vero C1008	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	2

Data from ChEMBL 36 via Core Engine