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Details

Stereochemistry ACHIRAL
Molecular Formula C22H29N3S2.2C4H4O4
Molecular Weight 631.76
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of THIETHYLPERAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CCSC1=CC=C2SC3=C(C=CC=C3)N(CCCN4CCN(C)CC4)C2=C1

InChI

InChIKey=RVBRTNPNFYFDMZ-SPIKMXEPSA-N
InChI=1S/C22H29N3S2.2C4H4O4/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24;2*5-3(6)1-2-4(7)8/h4-5,7-10,17H,3,6,11-16H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI
Molecular Formula C22H29N3S2
Molecular Weight 399.616
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Thiethylperazine is a antiemetic, which was used for the treatment of nausea and vomiting in patients undergoing radiotherapy, chemotherapy or as a postoperative care. Thiethylperazine exerts its therapeutic effect by blocking dopamine receptors in brain. The drug is capable of potentiating CNS depressants as well as atropine.

CNS Activity

Approval Year

1961
146
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8583
TORECAN

Approved Use

To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations.

Launch Date

1961
Secondary
Approved
8583
TORECAN

Approved Use

To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations.

Launch Date

1961
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day single, oral
Overdose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
unhealthy, 12
Health Status: unhealthy
Age Group: 12
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
Other AEs: Dystonia, Hyperreflexia...
Other AEs:
Dystonia
Hyperreflexia
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
150 mg 6 times / day multiple, oral
Highest studied dose
Dose: 150 mg, 6 times / day
Route: oral
Route: multiple
Dose: 150 mg, 6 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/99115/
unhealthy, 22-53
Health Status: unhealthy
Age Group: 22-53
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/99115/
Sources:
https://pubmed.ncbi.nlm.nih.gov/99115/
AEs

AEs

AESignificanceDosePopulation
Dystonia
100 mg 1 times / day single, oral
Overdose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
unhealthy, 12
Health Status: unhealthy
Age Group: 12
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
Hyperreflexia
100 mg 1 times / day single, oral
Overdose
Dose: 100 mg, 1 times / day
Route: oral
Route: single
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
unhealthy, 12
Health Status: unhealthy
Age Group: 12
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4184863/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MRP1
232
 yes
P-gp
1932
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:9544
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9544
ChemicalBook
CB7875007
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7875007
ZINC
ZINC000022446674
http://zinc15.docking.org/substances/ZINC000022446674
PubMed

PubMed

TitleDatePubMed
Cerebral amyloid-β proteostasis is regulated by the membrane transport protein ABCC1 in mice.
2011-10
Improving management of patients with advanced cancer.
2010-12-02
Acute ECG ST-segment elevation mimicking myocardial infarction in a patient with pulmonary embolism.
2010-11-24
Enhancement of vancomycin activity by phenothiazines against vancomycin-resistant Enterococcus faecium in vitro.
2010-08
High-degree atrioventricular block in acute ethanol poisoning: a case report.
2009-09-09
Drug treatment during pregnancy and isolated orofacial clefts in hungary.
2007-03
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.
2005-08
Evaluation of maternal infusion therapy during pregnancy for fetal development.
2005
Thiethylperazine-induced parkinsonism: in vivo demonstration of dopamine D2 receptors blockade.
2004-10
Case-control study of teratogenic potential of thiethylperazine, an anti-emetic drug.
2003-05
Structure-based computational database screening, in vitro assay, and NMR assessment of compounds that target TAR RNA.
2002-02
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001-07-07
Preliminary results. UFT/methotrexate/leucovorin for breast Ca patients in progression after HDCT/PBPC support.
1997-09
[Dyskinesis after a single dose of thiethylperazine during the first trimester of pregnancy].
1994-02-21
Chronic hemidystonia following acute dystonic reaction to thiethylperazine.
1991-06
Myoclonus associated with treatment with high doses of morphine: the role of supplemental drugs.
1989-07-15
Identification of phenothiazine antihistamines and their metabolites in urine.
1988
Recurrent dystonic reactions induced by thiethylperazine.
1985-07-01
Dystonic reactions following thiethylperazine in children.
1982-10
Thiethylperazine (Torecan)-associated dystonic reactions in children.
1979-12
[Extrapyramidal syndrome as a side-effect of treatment with thiethylperazine (torecan) and metoclopramide (Reglan) a review of ten cases (author's transl)].
1977-03
Dystonia and pyramidal signs after thiethylperazine overdose.
1969-09-06
Patents

Patents

CN105085434 A
3
EP20110755294
3

Sample Use Guides

In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:09 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:09 GMT 2025
Record UNII
RUK64CF26E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIETHYLPERAZINE MALEATE
MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
THIETHYLPERAZINE DIMALEATE
MI  
Preferred Name English
2-(Ethylthio)-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine maleate (1:2)
Systematic Name English
THIETHYLPERAZINE MALEATE [VANDF]
Common Name English
THIETHYLPERAZINE MALEATE [USAN]
Common Name English
THIETHYLPERAZINE MALEATE [USP IMPURITY]
Common Name English
THIETHYLPERAZINE DIMALEATE [MI]
Common Name English
THIETHYLPERAZINE MALEATE [ORANGE BOOK]
Common Name English
Thiethylperazine maleate [WHO-DD]
Common Name English
NSC-130044
Code English
GS-95
Code English
THIETHYLPERAZINE MALEATE [JAN]
Common Name English
10H-PHENOTHIAZINE, 2-(ETHYLTHIO)-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
THIETHYLPERAZINE MALEATE [MART.]
Common Name English
THIETHYLPERAZINE MALEATE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
Code System Code Type Description
EVMPD
SUB71453
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
EVMPD
SUB04808MIG
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
MERCK INDEX
m10737
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY Merck Index
FDA UNII
RUK64CF26E
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
NCI_THESAURUS
C29497
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
DRUG BANK
DBSALT001059
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
PUBCHEM
5282398
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
CAS
1179-69-7
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
CHEBI
32216
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
SMS_ID
100000091798
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL1378
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
NSC
130044
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
214-648-9
Created by admin on Mon Mar 31 17:46:09 GMT 2025 , Edited by admin on Mon Mar 31 17:46:09 GMT 2025
PRIMARY
Related Record Type Details
Structure of Maleic Acid
PARENT -> SALT/SOLVATE
Structure of THIETHYLPERAZINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of THIETHYLPERAZINE
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