CHLORPROTHIXENE ACETATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H19ClNS.C2H3O2
Molecular Weight	375.912
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC([O-])=O.C[NH+](C)CC\C=C1\C2=CC=CC=C2SC3=C1C=C(Cl)C=C3

InChI

InChIKey=XGKNWADXVDIFDQ-KIUKIJHYSA-N

InChI=1S/C18H18ClNS.C2H4O2/c1-20(2)11-5-7-14-15-6-3-4-8-17(15)21-18-10-9-13(19)12-16(14)18;1-2(3)4/h3-4,6-10,12H,5,11H2,1-2H3;1H3,(H,3,4)/b14-7-;

HIDE SMILES / InChI

Molecular Formula	C18H18ClNS
Molecular Weight	315.86
Charge	0
Count

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

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14065076
Curator's Comment: description was created based on several sources, including, http://www.mentalmeds.org/prescription_meds/Truxal.html, https://www.ncbi.nlm.nih.gov/pubmed/24071734

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 Target ID: CHEMBL2056 Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849	18.0 nM [Ki]
Serotonin (5-HT) receptor 34 Target ID: CHEMBL2096904 Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849
Histamine H1 receptor 316 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849	3.75 nM [Ki]
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: http://www.mentalmeds.org/prescription_meds/Truxal.html	Antagonist 2849	3.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16 Sources: https://www.medikamente-per-klick.de/images/ecommerce/08/48/08481217_2011-10_de_o.pdf	Primary		Approved 8583	TRUXAL Approved Use To treat psychosis.

C_max

Value	Dose	Co-administered	Analyte	Population
11 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1140253/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROTHIXENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
187 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1140253/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROTHIXENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1140253/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROTHIXENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
1800 mg 1 times / day multiple, oral Highest studied dose Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1314010	unhealthy, 25-49 years Health Status: unhealthy Age Group: 25-49 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1314010	Disc. AE: Polyneuropathy... AEs leading to discontinuation/dose reduction: Polyneuropathy (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1314010

AEs

AE	Significance	Dose	Population
Polyneuropathy	7 patients Disc. AE	1800 mg 1 times / day multiple, oral Highest studied dose Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1314010	unhealthy, 25-49 years Health Status: unhealthy Age Group: 25-49 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1314010

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 MRP2 499 P-gp 1741 OCT1 620 OATP2B1 157 OATP1B1 1079 OATP1B3 961 BSEP 550	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDkwOCJ9fQ%3D%3D	yes [IC50 27.47 uM]
BCRP 985	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0, https://www.sciencedirect.com/science/article/pii/S0928098717301343	yes [IC50 42 uM]
MRP2 625	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0, https://www.sciencedirect.com/science/article/pii/S0928098717301343	yes [IC50 74 uM]
OCT1 656	inhibitor 4027 Sources: https://pubs.acs.org/doi/10.1021/jm8003152	yes [IC50 77.8 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDkwOCJ9fQ%3D%3D	yes [Inhibition 20 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDkwOCJ9fQ%3D%3D	yes [Inhibition 20 uM]
OATP2B1 162	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDkwOCJ9fQ%3D%3D	yes [Inhibition 20 uM]
P-gp 1932	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098717301343	yes [Ki 31.4 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12438524/	no
CYP2D6 1388	substrate 4014 Sources: https://link.springer.com/chapter/10.1007%2F978-3-642-25761-2_10	yes

Sourcing

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

PubMed

Title	Date	PubMed
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.	2013-02	23243064
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.	1986-12	3105243

Sample Use Guides

In Vivo Use Guide

The usual adult dose is 15-100 mg (mild to moderate symptoms) or 100-400 mg (severe symptoms).

Route of Administration: Oral

In Vitro Use Guide

70 uM of cis-chlorprothixene produced approximately 50% inhibition of axonal transport measured in vitro in spinal nerves of the bullfrog.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:12:45 GMT 2025` Edited by `admin` on `Mon Mar 31 22:12:45 GMT 2025`
Record UNII	K45X4JP9Q1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-PROPANAMINE, 3-(2-CHLORO-9H-THIOXANTHEN-9-YLIDENE)-N,N-DIMETHYL-, (Z)-, ACETATE

Preferred Name

English

CHLORPROTHIXENE ACETATE

Common Name

English

Chlorprothixene acetate [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

K45X4JP9Q1