U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H29N3O2S2
Molecular Weight 443.6283
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of THIOTHIXENE

SMILES

CN(C)S(=O)(=O)c1ccc2c(c1)/C(=C(/[H])\CCN3CCN(C)CC3)/c4ccccc4S2

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
Curator's Comment:: Description was created based on several sources, including http://www.pfizer.com/files/products/uspi_navane.pdf | http://www.psychatlanta.com/psychatlanta/wp-content/uploads/navane.pdf | http://pubs.rsc.org/EN/content/articlelanding/1967/c1/c1967000743b#!divAbstract

Thiothixene (trade mark Navane) belongs to a class of antipsychotics known as the first-generation antipsychotics, sometimes referred to as conventional or typical antipsychotics. Thiothixene is a thioxanthene antipsychotic which elicits antipsychotic activity by postsynaptic blockade of CNS dopamine receptors resulting in inhibition of dopamine-mediated effects; also has alpha-adrenergic blocking activity. Thiothixene is effective in the management of schizophrenia. Only cis isomer of thiothixene exerts clinical effectivity.

Originator

Curator's Comment:: reference retrieved from http://www.druglead.com/cds/thiothixene.html # Pfizer

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAVANE

Approved Use

Thiothixene capsules are effective in the management of schizophrenia. Thiothixene capsules have not been evaluated in the management of behavioral complications in patients with mental retardation.

Launch Date

-7.7068796E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
27.2 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOTHIXENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
117 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOTHIXENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.7 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOTHIXENE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sex: unknown
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death
Sources:
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Hyperprolactinemia, Menstrual irregularity...
AEs leading to
discontinuation/dose reduction:
Hyperprolactinemia
Menstrual irregularity
Breast enlargement
Amenorrhea
Sources:
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Tardive dyskinesia, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Tardive dyskinesia
Neutropenia (severe)
Sources:
AEs

AEs

AESignificanceDosePopulation
Death Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sex: unknown
Sources:
Amenorrhea Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Breast enlargement Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Hyperprolactinemia Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Menstrual irregularity Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Tardive dyskinesia Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Neutropenia severe
Disc. AE
20 mg 1 times / day multiple, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 65 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Once versus thrice daily thiothixene in the treatment of schizophrenic in-patients.
1974 Jul
Drug-induced dystonia.
1975 May
Fever, tachycardia, and hypertension with acute catatonic schizophrenia.
1978 Jul
Benztropine prophylaxis of dystonic reactions.
1979 Mar 28
Separation and quantitation of cis- and trans-thiothixene in human plasma by high-performance liquid chromatography.
1982 Dec 10
Psychopharmacological correlates of post-psychotic depression: a double-blind investigation of haloperidol vs thiothixene in outpatient schizophrenia.
1982 Mar
Neurotoxicity in patients with schizophrenia during lithium therapy.
1982 May-Jun
Desipramine-associated hepatitis.
1983 Aug
Neuroleptic malignant syndrome and malignant hyperthermia.
1983 Jan 29
Maprotiline hydrochloride associated with a clinical state of catatonic stupor and epileptic encephalogram.
1984 Aug
Akathisia with haloperidol and thiothixene.
1984 Nov
Improved high-performance liquid chromatographic method for the quantitation of cis-thiothixene in plasma samples using trans-thiothixene as internal standard.
1984 Nov 28
Manic syndrome associated with zidovudine treatment.
1988 Jun 17
On the selection of mice for haloperidol response and non-response.
1991
Esophageal atony and dilatation as a side effect of thiothixene and benztropine.
1993 Jul
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
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
2003 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
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 Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
NDF-RT N0000180182
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
WHO-VATC QN05AF04
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
WHO-ATC N05AF04
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
NCI_THESAURUS C29710
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
Code System Code Type Description
CAS
5591-45-7
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
THIOTHIXENE
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
LACTMED
Thiothixene
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
NCI_THESAURUS
C47752
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
USP_CATALOG
1665003
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY USP-RS
FDA UNII
7318FJ13YJ
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
MERCK INDEX
M10789
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY Merck Index
EVMPD
SUB11094MIG
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
DRUG BANK
DB01623
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
EPA CompTox
3313-26-6
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
CAS
3313-26-6
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
RXCUI
10510
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY RxNorm
MESH
D013888
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
DRUG CENTRAL
2639
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
IUPHAR
212
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
MERCK INDEX
M10789
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
INN
2114
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY
PUBCHEM
941651
Created by admin on Sat Jun 26 12:51:46 UTC 2021 , Edited by admin on Sat Jun 26 12:51:46 UTC 2021
PRIMARY