THIETHYLPERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H29N3S2
Molecular Weight	399.616
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCSC1=CC=C2SC3=CC=CC=C3N(CCCN4CCN(C)CC4)C2=C1

InChI

InChIKey=XCTYLCDETUVOIP-UHFFFAOYSA-N

InChI=1S/C22H29N3S2/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/h4-5,7-10,17H,3,6,11-16H2,1-2H3

HIDE SMILES / InChI

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 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting 38 Sources: http://www.aana.com/newsandjournal/Documents/letters_1276_p583.pdf	Secondary		Approved 8583	TORECAN Approved Use To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations. Launch Date 1961
Nausea 63 Sources: http://www.aana.com/newsandjournal/Documents/letters_1276_p583.pdf	Secondary		Approved 8583	TORECAN Approved Use To relieve nausea and vomitin associated with postoperative recovery, radiation therapy, chemotherapy, acute situations. Launch Date 1961

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 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

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 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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP1 232	activator 342 Sources: https://iv.iiarjournals.org/content/23/6/943	yes
P-gp 1932	inhibitor 4027 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
Cerebral amyloid-β proteostasis is regulated by the membrane transport protein ABCC1 in mice.	2011-10	21881209
Improving management of patients with advanced cancer.	2010-12-02	21206517
Acute ECG ST-segment elevation mimicking myocardial infarction in a patient with pulmonary embolism.	2010-11-24	21106090
Enhancement of vancomycin activity by phenothiazines against vancomycin-resistant Enterococcus faecium in vitro.	2010-08	20353486
High-degree atrioventricular block in acute ethanol poisoning: a case report.	2009-09-09	19918387
Drug treatment during pregnancy and isolated orofacial clefts in hungary.	2007-03	17328645
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.	2005-08	16101941
Evaluation of maternal infusion therapy during pregnancy for fetal development.	2005	16239951
Thiethylperazine-induced parkinsonism: in vivo demonstration of dopamine D2 receptors blockade.	2004-10	15469457
Case-control study of teratogenic potential of thiethylperazine, an anti-emetic drug.	2003-05	12742335
Structure-based computational database screening, in vitro assay, and NMR assessment of compounds that target TAR RNA.	2002-02	11880033
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.	2001-07-07	11440936
Preliminary results. UFT/methotrexate/leucovorin for breast Ca patients in progression after HDCT/PBPC support.	1997-09	9348575
[Dyskinesis after a single dose of thiethylperazine during the first trimester of pregnancy].	1994-02-21	8084830
Chronic hemidystonia following acute dystonic reaction to thiethylperazine.	1991-06	1880525
Myoclonus associated with treatment with high doses of morphine: the role of supplemental drugs.	1989-07-15	2475196
Identification of phenothiazine antihistamines and their metabolites in urine.	1988	2904251
Recurrent dystonic reactions induced by thiethylperazine.	1985-07-01	4028959
Dystonic reactions following thiethylperazine in children.	1982-10	7147262
Thiethylperazine (Torecan)-associated dystonic reactions in children.	1979-12	514725
[Extrapyramidal syndrome as a side-effect of treatment with thiethylperazine (torecan) and metoclopramide (Reglan) a review of ten cases (author's transl)].	1977-03	875594
Dystonia and pyramidal signs after thiethylperazine overdose.	1969-09-06	4184863

Patents

Sample Use Guides

In Vivo Use Guide

Administer 10 mg 1-3 times/day.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

THIETHYLPERAZINE

Official Name

English

THIETHYLPERAZINE [HSDB]

Preferred Name

English

THIETHYLPERAZINE [MI]

Common Name

English

thiethylperazine [INN]

Common Name

English

THIETHYLPERAZINE [MART.]

Common Name

English

Thiethylperazine [WHO-DD]

Common Name

English

THIETHYLPERAZINE [USAN]

Common Name

English

THIETHYLPERAZINE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QR06AD03