CHLORPROTHIXENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H18ClNS
Molecular Weight	315.86
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CN(C)CC\C=C1\C2=CC=CC=C2SC3=CC=C(Cl)C=C13

InChI

InChIKey=WSPOMRSOLSGNFJ-AUWJEWJLSA-N

InChI=1S/C18H18ClNS/c1-20(2)11-5-7-14-15-6-3-4-8-17(15)21-18-10-9-13(19)12-16(14)18/h3-4,6-10,12H,5,11H2,1-2H3/b14-7-

HIDE SMILES / InChI

Molecular Formula	C18H18ClNS
Molecular Weight	315.86
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

Chlorprothixene (Taractan, Tarasan, Truxal) is a thioxanthine derivative developed by Lundbeck for the treatment of psychotic disorders. The drug exerts its activity by binding to and inhibiting serotonin receptors, dopamine receptors, muscarinic acetylcholine receptor, histamine H1 receptor and alpha1-adrenergic receptor.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D1 receptor 106	Antagonist 2,849	18.0 nM [Ki]
Serotonin (5-HT) receptor 34	Antagonist 2,849
Adrenergic receptor alpha-1 171	Antagonist 2,849
Histamine H1 receptor 316	Antagonist 2,849	3.75 nM [Ki]
Muscarinic acetylcholine receptor 162	Antagonist 2,849
D(2) dopamine receptor 58	Antagonist 2,849	3.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16	Primary		Approved 8,583	TRUXAL

C_max

Value	Dose	Co-administered	Analyte	Population
11 ng/mL	15 mg single, oral		CHLORPROTHIXENE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
187 ng × h/mL	15 mg single, oral		CHLORPROTHIXENE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.4 h	15 mg single, oral		CHLORPROTHIXENE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
1800 mg 1 times / day multiple, oral Highest studied dose	unhealthy, 25-49 years	Disc. AE: Polyneuropathy...

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AEs

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AE	Significance	Dose	Population
Polyneuropathy	7 patients Disc. AE	1800 mg 1 times / day multiple, oral Highest studied dose	unhealthy, 25-49 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 MRP2 499 P-gp 1,741 OCT1 620 OATP2B1 157 OATP1B1 1,079 OATP1B3 961 BSEP 550	P-gp 2,052

Drug as perpetrator

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Target	Modality	Activity
BSEP 554	inhibitor 4,027	yes [IC50 27.47 uM]
BCRP 985	inhibitor 4,027	yes [IC50 42 uM]
MRP2 625	inhibitor 4,027	yes [IC50 74 uM]
OCT1 656	inhibitor 4,027	yes [IC50 77.8 uM]
OATP1B1 1,095	inhibitor 4,027	yes [Inhibition 20 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2,052	substrate 4,014	no
CYP2D6 1,388	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3651	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3651
eMolecules	1986150	https://www.emolecules.com/cgi-bin/more?vid=1986150

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PubMed

PubMed

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Title	Date	PubMed
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.	1986 Dec	3105243
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.	2013 Feb	23243064