THIOPROPAZATE

US Previously Marketed

First approved in 1957

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H28ClN3O2S
Molecular Weight	446.005
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OCCN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1

InChI

InChIKey=AIUHRQHVWSUTGJ-UHFFFAOYSA-N

InChI=1S/C23H28ClN3O2S/c1-18(28)29-16-15-26-13-11-25(12-14-26)9-4-10-27-20-5-2-3-6-22(20)30-23-8-7-19(24)17-21(23)27/h2-3,5-8,17H,4,9-16H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14399273 | https://pubchem.ncbi.nlm.nih.gov/compound/6762

THIOPROPAZATE, a phenothiazine derivative, is a typical antipsychotic. It is a prodrug to perphenazine.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
choreatic disorders 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4253070	Primary		Approved 8429	Dartal Approved Use Unknown

Doses

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4130307 Page: p.105	unhealthy, 33 - 60 n = 10 Health Status: unhealthy Condition: Huntington’s chorea Age Group: 33 - 60 Sex: M+F Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/4130307 Page: p.105	Disc. AE: Parkinsonism... AEs leading to discontinuation/dose reduction: Parkinsonism (10%) Sources: https://pubmed.ncbi.nlm.nih.gov/4130307 Page: p.105
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/381595 Page: p.578	unhealthy, 39 - 69 n = 15 Health Status: unhealthy Condition: Tardive dyskinesia Age Group: 39 - 69 Sex: M+F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/381595 Page: p.578	Disc. AE: Parkinsonism... AEs leading to discontinuation/dose reduction: Parkinsonism (20%) Sources: https://pubmed.ncbi.nlm.nih.gov/381595 Page: p.578
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4555826 Page: p.100	unhealthy, 44 - 70 n = 4 Health Status: unhealthy Condition: Tardive dyskinesia Age Group: 44 - 70 Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/4555826 Page: p.100	Sources: https://pubmed.ncbi.nlm.nih.gov/4555826 Page: p.100

AEs

AE	Significance	Dose	Population
Parkinsonism	10% Disc. AE	30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4130307 Page: p.105	unhealthy, 33 - 60 n = 10 Health Status: unhealthy Condition: Huntington’s chorea Age Group: 33 - 60 Sex: M+F Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/4130307 Page: p.105
Parkinsonism	20% Disc. AE	30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/381595 Page: p.578	unhealthy, 39 - 69 n = 15 Health Status: unhealthy Condition: Tardive dyskinesia Age Group: 39 - 69 Sex: M+F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/381595 Page: p.578

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:59119	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59119
ZINC	ZINC000022446680	http://zinc15.docking.org/substances/ZINC000022446680

PubMed

Title	Date	PubMed
Acetophenazine (Tindal) and thiopropazate (Dartal) in ambulatory psychoneurotic patients.	1961 Oct	13883575
Persistent tardive dyskinesia.	1971 Sep 4	5106314
A double-blind trial of tetrabenazine, thiopropazate, and placebo in patients with chorea.	1974 Jan 26	4130307

Name

Type

Language

THIOPROPAZATE

Official Name

English

4-(3-(2-CHLOROPHENOTHIAZIN-10-YL)PROPYL)-1-PIPERAZINEETHANOL ACETATE

Systematic Name

English

THIOPROPAZATE [MI]

Common Name

English

THIOPROPAZATE [HSDB]

Common Name

English

Thiopropazate [WHO-DD]

Common Name

English

thiopropazate [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05AB05