THIETHYLPERAZINE MALATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H29N3S2.2C4H6O5
Molecular Weight	667.791
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(CC(O)=O)C(O)=O.OC(CC(O)=O)C(O)=O.CCSC1=CC2=C(SC3=C(C=CC=C3)N2CCCN4CCN(C)CC4)C=C1

InChI

InChIKey=GTHHLZDYRHLACN-UHFFFAOYSA-N

InChI=1S/C22H29N3S2.2C4H6O5/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*5-2(4(8)9)1-3(6)7/h4-5,7-10,17H,3,6,11-16H2,1-2H3;2*2,5H,1H2,(H,6,7)(H,8,9)

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 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 1961
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 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 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
Dystonia and pyramidal signs after thiethylperazine overdose.	1969 Sep 6	4184863
[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
Recurrent dystonic reactions induced by thiethylperazine.	1985 Jul-Aug	4028959
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
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.	2001 Jul 7	11440936
Structure-based computational database screening, in vitro assay, and NMR assessment of compounds that target TAR RNA.	2002 Feb	11880033
Case-control study of teratogenic potential of thiethylperazine, an anti-emetic drug.	2003 May	12742335

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 MALATE

Common Name

English

THIETHYLPERAZINE MALATE [JAN]

Common Name

English

10H-PHENOTHIAZINE, 2-(ETHYLTHIO)-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, 2-HYDROXY-1,4-BUTANEDIOATE (1:2)

Systematic Name

English

2-(Ethylthio)-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine malate (1:2)

Systematic Name

English

THIETHYLPERAZINE MALATE [ORANGE BOOK]

Common Name

English

THIETHYLPERAZINE MALATE [MART.]

Common Name

English

THIETHYLPERAZINE DIMALATE [MI]

Common Name

English

THIETHYLPERAZINE DIMALATE

Common Name

English

TORECAN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710