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Details

Stereochemistry ACHIRAL
Molecular Formula C23H29N3O2S2
Molecular Weight 443.625
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of THIOTHIXENE

SMILES

CN(C)S(=O)(=O)C1=CC2=C(SC3=C(C=CC=C3)\C2=C\CCN4CCN(C)CC4)C=C1

InChI

InChIKey=GFBKORZTTCHDGY-UWVJOHFNSA-N
InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8-

HIDE SMILES / InChI

Description

THIOTHIXENE, (E)- (trans-thiothixene) )is a clinically inactive isomer of thiothixene. 1000 times higher concentration of this isomer than the active cis-isomer required to inhibit release of (3H) dopamine from rat striatal slices. Trans-thiothixene is about 50 times less potent than cis-thiothixene in inhibiting 3H-haloperidol binding at their binding sites in the rat brain. Cis-isomer of thiothixene is the active antipsychotic drug used in antipsychotic therapy.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Fever, tachycardia, and hypertension with acute catatonic schizophrenia.
1978 Jul
Subjective response to antipsychotic drugs.
1981 Feb
Motility, Parkinsonism, and prolactin with thiothixene and thioridazine.
1981 Jun
Psychopharmacological correlates of post-psychotic depression: a double-blind investigation of haloperidol vs thiothixene in outpatient schizophrenia.
1982 Mar
Desipramine-associated hepatitis.
1983 Aug
Akathisia with haloperidol and thiothixene.
1984 Nov
Esophageal atony and dilatation as a side effect of thiothixene and benztropine.
1993 Jul
Neuroleptic-induced extrapyramidal side effects.
1993 Nov
Fluoxetine and visual hallucinations in dementia.
1995 Oct 15
Metabolites of the antipsychotic agent clozapine inhibit the replication of human immunodeficiency virus type 1.
1997 May 3
Patents

Sample Use Guides

In Vivo Use Guide
Schizophrenia: Oral: Initial: Mild-to-moderate symptoms: 2 mg 3 times daily; usual dose 15 mg daily; severe symptoms: 5 mg twice daily; usual dose 20-30 mg daily. Increase dose gradually. Maximum: 60 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Both the activities of the splenic NK cell cytotoxicity and the effector-target cell conjugation were suppressed by thiothixine, fluphenazine, and trifluoperazine at concentrations from 2.64 to 14.78 microM.
Name Type Language
THIOTHIXENE
MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
THIOTHIXENE [ORANGE BOOK]
Common Name English
P-4657 B
Code English
THIOTHIXENE [USAN]
Common Name English
P-4657B
Code English
THIOTHIXENE [USP-RS]
Common Name English
(Z)-THIOTHIXENE
Common Name English
TIOTIXENE
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
TIOTIXENE [INN]
Common Name English
THIOTHIXENE [VANDF]
Common Name English
(Z)-N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)THIOXANTHENE-2-SULFONAMIDE
Systematic Name English
NAVANE
Brand Name English
CP-12252-1
Code English
THIOTHIXENE [USP]
Common Name English
N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)THIOXANTHENE-2-SULFONAMIDE
Systematic Name English
TIOTIXENE [WHO-DD]
Common Name English
NSC-108165
Code English
CIS-THIOTHIXENE
Common Name English
TIOTIXENE [JAN]
Common Name English
TIOTIXENE [MART.]
Common Name English
THIOTHIXENE CIS-ISOMER [MI]
Common Name English
ORBINAMON
Brand Name English
9H-THIOXANTHENE-2-SULFONAMIDE, N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)-, (Z)-
Systematic Name English
THIOTHIXENE [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX 956
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
NDF-RT N0000180182
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
WHO-VATC QN05AF04
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
WHO-ATC N05AF04
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
Code System Code Type Description
CAS
5591-45-7
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
THIOTHIXENE
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
NCI_THESAURUS
C47752
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
MERCK INDEX
M10789
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY Merck Index
EVMPD
SUB11094MIG
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
EPA CompTox
3313-26-6
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
CAS
3313-26-6
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
RXCUI
10510
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY RxNorm
MESH
D013888
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
IUPHAR
212
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
MERCK INDEX
M10789
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL1201
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
INN
2114
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY
PUBCHEM
941651
Created by admin on Tue Mar 06 12:15:18 UTC 2018 , Edited by admin on Tue Mar 06 12:15:18 UTC 2018
PRIMARY SWITZERF