U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H18ClNS.ClH
Molecular Weight 352.321
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROTHIXENE HYDROCHLORIDE

SMILES

Cl.CN(C)CC\C=C1\C2=CC=CC=C2SC3=C1C=C(Cl)C=C3

InChI

InChIKey=YWKRLOSRDGPEJR-KIUKIJHYSA-N
InChI=1S/C18H18ClNS.ClH/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;1H/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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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

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 Wed Jul 05 22:39:10 UTC 2023
Edited
by admin
on Wed Jul 05 22:39:10 UTC 2023
Record UNII
268KCR965N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORPROTHIXENE HYDROCHLORIDE
EP   JAN   MART.   MI   WHO-DD  
Common Name English
1-PROPANAMINE, 3-(2-CHLORO-9H-THIOXANTHEN-9-YLIDENE)-N,N-DIMETHYL-, HYDROCHLORIDE (1:1), (3Z)-
Common Name English
CHLORPROTHIXENE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
CHLORPROTHIXENE HYDROCHLORIDE [MI]
Common Name English
CHLORPROTHIXENE HYDROCHLORIDE [EP IMPURITY]
Common Name English
CHLORPROTHIXENE HCL
Common Name English
Chlorprothixene hydrochloride [WHO-DD]
Common Name English
CHLORPROTHIXENE HYDROCHLORIDE [JAN]
Common Name English
CHLORPROTHIXENE HYDROCHLORIDE [MART.]
Common Name English
Code System Code Type Description
RXCUI
91133
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M3464
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY Merck Index
PUBCHEM
5282478
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
CAS
1229-38-5
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
ALTERNATIVE
FDA UNII
268KCR965N
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID701017267
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
229-289-3
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
CAS
6469-93-8
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
EVMPD
SUB01257MIG
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
SMS_ID
100000092777
Created by admin on Wed Jul 05 22:39:10 UTC 2023 , Edited by admin on Wed Jul 05 22:39:10 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
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ACTIVE MOIETY