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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.

CNS Activity

Originator

Lundbeck
43
Sources: ISBN: 978-0-471-89980-8

Approval Year

1962
69
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 18.0 nM [Ki]
Antagonist
2778
Antagonist
2778
Histamine H1 receptor
315
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
Antagonist
2778
 3.75 nM [Ki]
Antagonist
2778
D(2) dopamine receptor
58
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Antagonist
2778
 3.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TRUXAL

Approved Use

To treat psychosis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
https://pubmed.ncbi.nlm.nih.gov/1314010
unhealthy, 25-49 years
n = 7
Health Status: unhealthy
Age Group: 25-49 years
Sex: M+F
Population Size: 7
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

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:
https://pubmed.ncbi.nlm.nih.gov/1314010
unhealthy, 25-49 years
n = 7
Health Status: unhealthy
Age Group: 25-49 years
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/1314010
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
BCRP
699

MRP2
383

P-gp
1461

OCT1
512

OATP2B1
123

OATP1B1
788

OATP1B3
706

BSEP
402
P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
403
 yes [IC50 27.47 uM]
BCRP
773
 yes [IC50 42 uM]
MRP2
475
 yes [IC50 74 uM]
OCT1
543
 yes [IC50 77.8 uM]
OATP1B1
803
 yes [Inhibition 20 uM]
OATP1B3
715
 yes [Inhibition 20 uM]
OATP2B1
126
 yes [Inhibition 20 uM]
P-gp
1650
 yes [Ki 31.4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
CYP2D6
1217
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

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

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 Fri Dec 15 15:07:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:14 GMT 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 Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m3464
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY Merck Index
PUBCHEM
5282478
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
CAS
1229-38-5
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
ALTERNATIVE
FDA UNII
268KCR965N
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID701017267
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
229-289-3
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
CAS
6469-93-8
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
EVMPD
SUB01257MIG
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
SMS_ID
100000092777
Created by admin on Fri Dec 15 15:07:15 GMT 2023 , Edited by admin on Fri Dec 15 15:07:15 GMT 2023
PRIMARY
Related Record Type Details
Structure of CHLORPROTHIXENE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DEMETHYLCHLORPROTHIXENE
IMPURITY -> PARENT
Structure of 3-(4-Chloro-9H-thioxanthen-9-ylidene)-N,N-dimethylpropan-1-amine, (Z)-
IMPURITY -> PARENT
Structure of 2-Chloro-9-[3-(dimethylamino)propyl]-9H-thioxanthen-9-ol
IMPURITY -> PARENT
Structure of Chlorprothixene, (E)-
IMPURITY -> PARENT
Structure of 2-CHLOROTHIOXANTHONE
IMPURITY -> PARENT
Structure of PROTHIXENE
IMPURITY -> PARENT
Related Record Type Details
Structure of CHLORPROTHIXENE
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