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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18ClNS
Molecular Weight 315.8619
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROTHIXENE

SMILES

CN(C)CC/C(/[H])=C\1/c2ccccc2Sc3ccc(cc13)Cl

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 315.8619
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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.

Originator

Sources: ISBN: 978-0-471-89980-8

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
18.0 nM [Ki]
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
3.75 nM [Ki]
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
3.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRUXAL

Approved Use

To treat psychosis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
187 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.4 h
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

Doses

DosePopulationAdverse events​
1800 mg 1 times / day multiple, oral (max)
Highest studied dose
Dose: 1800 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1800 mg, 1 times / day
Sources:
unhealthy, 25-49 years
n = 7
Health Status: unhealthy
Age Group: 25-49 years
Sex: M+F
Population Size: 7
Sources:
Disc. AE: Polyneuropathy...
AEs leading to
discontinuation/dose reduction:
Polyneuropathy (7 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Polyneuropathy 7 patients
Disc. AE
1800 mg 1 times / day multiple, oral (max)
Highest studied dose
Dose: 1800 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1800 mg, 1 times / day
Sources:
unhealthy, 25-49 years
n = 7
Health Status: unhealthy
Age Group: 25-49 years
Sex: M+F
Population Size: 7
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 27.47 uM]
yes [IC50 42 uM]
yes [IC50 74 uM]
yes [IC50 77.8 uM]
yes [Inhibition 20 uM]
yes [Inhibition 20 uM]
yes [Inhibition 20 uM]
yes [Ki 31.4 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
The antibacterial effect of selected phenothiazines and thioxanthenes on slow-growing mycobacteria.
1986 Dec
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

Sample Use Guides

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 Sat Jun 26 00:36:37 UTC 2021
Edited
by admin
on Sat Jun 26 00:36:37 UTC 2021
Record UNII
9S7OD60EWP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORPROTHIXENE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
RO-40403
Code English
N-714RO 4-0403
Code English
N-714
Code English
CHLORPROTHIXENE [MI]
Common Name English
CHLORPROTHIXENE [ORANGE BOOK]
Common Name English
CHLORPROTHIXENE [MART.]
Common Name English
CHLORPROTHIXENE [JAN]
Common Name English
RO-4-0403
Code English
CHLORPROTHIXENE [INN]
Common Name English
TARACTAN
Brand Name English
1-PROPANAMINE, 3-(2-CHLORO-9H-THIOXANTHEN-9-YLIDENE)-N,N-DIMETHYL-, (Z)-
Systematic Name English
CHLORPROTHIXENE [WHO-DD]
Common Name English
CHLORPROTHIXENE [VANDF]
Common Name English
CHLORPROTHIXENE [USAN]
Common Name English
NSC-18720
Code English
CHLORPROTHIXENE [HSDB]
Common Name English
(Z)-2-CHLORO-N,N-DIMETHYLTHIOXANTHENE-.DELTA.(SUP 9,.GAMMA.)-PROPYLAMINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
WHO-VATC QN05AF03
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
WHO-ATC N05AF03
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
Code System Code Type Description
RXCUI
2406
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY RxNorm
PUBCHEM
667467
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
NCI_THESAURUS
C65325
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL908
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
MERCK INDEX
M3464
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY Merck Index
CAS
113-59-7
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
FDA UNII
9S7OD60EWP
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
EPA CompTox
113-59-7
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
WIKIPEDIA
CHLORPROTHIXENE
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
HSDB
2808
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
DRUG BANK
DB01239
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
INN
886
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
DRUG CENTRAL
623
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-032-8
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
EVMPD
SUB06210MIG
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
MESH
D002749
Created by admin on Sat Jun 26 00:36:38 UTC 2021 , Edited by admin on Sat Jun 26 00:36:38 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY