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Details

Stereochemistry ACHIRAL
Molecular Formula C22H29N3S2.2C4H4O4
Molecular Weight 631.76
Optical Activity UNSPECIFIED
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
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
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
TORECAN
Secondary
TORECAN
PubMed

PubMed

TitleDatePubMed
Dystonia and pyramidal signs after thiethylperazine overdose.
1969 Sep 6
[Extrapyramidal syndrome as a side-effect of treatment with thiethylperazine (torecan) and metoclopramide (Reglan) a review of ten cases (author's transl)].
1977 Mar
Thiethylperazine (Torecan)-associated dystonic reactions in children.
1979 Dec
Dystonic reactions following thiethylperazine in children.
1982 Oct
Recurrent dystonic reactions induced by thiethylperazine.
1985 Jul-Aug
Identification of phenothiazine antihistamines and their metabolites in urine.
1988
Myoclonus associated with treatment with high doses of morphine: the role of supplemental drugs.
1989 Jul 15
Chronic hemidystonia following acute dystonic reaction to thiethylperazine.
1991 Jun
[Dyskinesis after a single dose of thiethylperazine during the first trimester of pregnancy].
1994 Feb 21-28
Preliminary results. UFT/methotrexate/leucovorin for breast Ca patients in progression after HDCT/PBPC support.
1997 Sep
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001 Jul 7
Structure-based computational database screening, in vitro assay, and NMR assessment of compounds that target TAR RNA.
2002 Feb
Case-control study of teratogenic potential of thiethylperazine, an anti-emetic drug.
2003 May
Thiethylperazine-induced parkinsonism: in vivo demonstration of dopamine D2 receptors blockade.
2004 Oct
Evaluation of maternal infusion therapy during pregnancy for fetal development.
2005
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.
2005 Aug
Drug treatment during pregnancy and isolated orofacial clefts in hungary.
2007 Mar
High-degree atrioventricular block in acute ethanol poisoning: a case report.
2009 Sep 9
Enhancement of vancomycin activity by phenothiazines against vancomycin-resistant Enterococcus faecium in vitro.
2010 Aug
Improving management of patients with advanced cancer.
2010 Dec 2
Acute ECG ST-segment elevation mimicking myocardial infarction in a patient with pulmonary embolism.
2010 Nov 24
Cerebral amyloid-β proteostasis is regulated by the membrane transport protein ABCC1 in mice.
2011 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Administer 10 mg 1-3 times/day.
Route of Administration: Oral; Rectal; Intramuscular
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:42:24 UTC 2019
Edited
by admin
on Tue Oct 22 00:42:24 UTC 2019
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
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 DIMALEATE [MI]
Common Name English
THIETHYLPERAZINE MALEATE [USP]
Common Name English
THIETHYLPERAZINE MALEATE [ORANGE BOOK]
Common Name English
GS-95
Code English
THIETHYLPERAZINE MALEATE [WHO-DD]
Common Name English
10H-PHENOTHIAZINE, 2-(ETHYLTHIO)-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
NSC-130044
Code English
THIETHYLPERAZINE MALEATE [MART.]
Common Name English
THIETHYLPERAZINE MALEATE [USP-RS]
Common Name English
THIETHYLPERAZINE DIMALEATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
Code System Code Type Description
EVMPD
SUB71453
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
EVMPD
SUB04808MIG
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
MERCK INDEX
M10737
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C29497
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
CAS
1179-69-7
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL1378
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
214-648-9
Created by admin on Tue Oct 22 00:42:24 UTC 2019 , Edited by admin on Tue Oct 22 00:42:24 UTC 2019
PRIMARY
Related Record Type Details
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY