THIETHYLPERAZINE MALEATE

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 Search

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CCSC1=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(C)CC4)C=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
Sources: ISBN: 978-1-4160-0208-6, Shorr R.I., 'Drugs for the Geriatric Patient' (2007), p. 1203, Retrieved from https://books.google.com/books?id=-gmjBQAAQBAJ&dq | http://www.aana.com/newsandjournal/Documents/letters_1276_p583.pdf

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

Primary Target	Pharmacology	Condition	Potency
Dopamine receptor 60 Target ID: CHEMBL2096905 Sources: ISBN: 978-1-4160-0208-6, Shorr R.I., 'Drugs for the Geriatric Patient' (2007), p. 1203, Retrieved from https://books.google.com/books?id=-gmjBQAAQBAJ&dq	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting 38 Sources: http://www.aana.com/newsandjournal/Documents/letters_1276_p583.pdf	Secondary		Approved 8429	TORECAN Approved Use To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations. Launch Date -2.66889593E11
Nausea 63 Sources: http://www.aana.com/newsandjournal/Documents/letters_1276_p583.pdf	Secondary		Approved 8429	TORECAN Approved Use To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations. Launch Date -2.66889593E11

Doses

Dose	Population	Adverse 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 n = 1 Health Status: unhealthy Condition: migraine Age Group: 12 Sex: F Population Size: 1 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 (max) 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 n = 10 Health Status: unhealthy Condition: schizophrenia Age Group: 22-53 Sex: M+F Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/99115/	Sources: https://pubmed.ncbi.nlm.nih.gov/99115/

AEs

AE	Significance	Dose	Population
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 n = 1 Health Status: unhealthy Condition: migraine Age Group: 12 Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: migraine Age Group: 12 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4184863/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP1 172	activator 214 Sources: https://iv.iiarjournals.org/content/23/6/943	yes
P-gp 1650	inhibitor 3277 Sources: https://iv.iiarjournals.org/content/23/6/943	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
[Extrapyramidal syndrome as a side-effect of treatment with thiethylperazine (torecan) and metoclopramide (Reglan) a review of ten cases (author's transl)].	1977 Mar	875594
Thiethylperazine (Torecan)-associated dystonic reactions in children.	1979 Dec	514725
Dystonic reactions following thiethylperazine in children.	1982 Oct	7147262
Identification of phenothiazine antihistamines and their metabolites in urine.	1988	2904251
Chronic hemidystonia following acute dystonic reaction to thiethylperazine.	1991 Jun	1880525
[Dyskinesis after a single dose of thiethylperazine during the first trimester of pregnancy].	1994 Feb 21-28	8084830
Preliminary results. UFT/methotrexate/leucovorin for breast Ca patients in progression after HDCT/PBPC support.	1997 Sep	9348575
Thiethylperazine-induced parkinsonism: in vivo demonstration of dopamine D2 receptors blockade.	2004 Oct	15469457
Evaluation of maternal infusion therapy during pregnancy for fetal development.	2005	16239951
Drug treatment during pregnancy and isolated orofacial clefts in hungary.	2007 Mar	17328645
High-degree atrioventricular block in acute ethanol poisoning: a case report.	2009 Sep 9	19918387
Enhancement of vancomycin activity by phenothiazines against vancomycin-resistant Enterococcus faecium in vitro.	2010 Aug	20353486
Improving management of patients with advanced cancer.	2010 Dec 2	21206517
Acute ECG ST-segment elevation mimicking myocardial infarction in a patient with pulmonary embolism.	2010 Nov 24	21106090
Cerebral amyloid-β proteostasis is regulated by the membrane transport protein ABCC1 in mice.	2011 Oct	21881209

Patents

Sample Use Guides

In Vivo Use Guide

Administer 10 mg 1-3 times/day.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:32 UTC 2023` Edited by `admin` on `Fri Dec 15 15:05:32 UTC 2023`
Record UNII	RUK64CF26E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

THIETHYLPERAZINE MALEATE

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 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

THIETHYLPERAZINE DIMALEATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267