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Details

Stereochemistry ACHIRAL
Molecular Formula C23H29N3O2S2.2ClH
Molecular Weight 516.547
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of THIOTHIXENE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=SSRKPUYBAUMQED-INHJUQNSSA-N
InChI=1S/C23H29N3O2S2.2ClH/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;2*1H/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

1967
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
Drug-induced dystonia.
1975 May
Fever, tachycardia, and hypertension with acute catatonic schizophrenia.
1978 Jul
Benztropine prophylaxis of dystonic reactions.
1979 Mar 28
Thiothixene plasma levels and clinical response in acute schizophrenia.
1981 May
Separation and quantitation of cis- and trans-thiothixene in human plasma by high-performance liquid chromatography.
1982 Dec 10
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
Rapid tranquilization: a comparison of thiothixene with loxapine.
1986 Jun
Manic syndrome associated with zidovudine treatment.
1988 Jun 17
Esophageal atony and dilatation as a side effect of thiothixene and benztropine.
1993 Jul
Neuroleptic-induced extrapyramidal side effects.
1993 Nov
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
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Density functional theory study of structural and electronic properties of trans and cis structures of thiothixene as a nano-drug.
2017 Nov 25
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
THIOTHIXENE HYDROCHLORIDE ANHYDROUS
Common Name English
9H-THIOXANTHENE-2-SULFONAMIDE, N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)-, DIHYDROCHLORIDE, (Z)-
Common Name English
9H-THIOXANTHENE-2-SULFONAMIDE, N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)-, DIHYDROCHLORIDE, (9Z)-
Systematic Name English
THIOTHIXENE DIHYDROCHLORIDE ANHYDROUS
Common Name English
Tiotixene Hydrochloride [WHO-DD]
Common Name English
THIOTHIXENE DIHYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
58513-59-0
Created by admin on Fri Dec 15 19:41:55 GMT 2023 , Edited by admin on Fri Dec 15 19:41:55 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID30109999
Created by admin on Fri Dec 15 19:41:55 GMT 2023 , Edited by admin on Fri Dec 15 19:41:55 GMT 2023
PRIMARY
FDA UNII
2P7AT1AU06
Created by admin on Fri Dec 15 19:41:55 GMT 2023 , Edited by admin on Fri Dec 15 19:41:55 GMT 2023
PRIMARY
PUBCHEM
9958173
Created by admin on Fri Dec 15 19:41:55 GMT 2023 , Edited by admin on Fri Dec 15 19:41:55 GMT 2023
PRIMARY
CAS
49746-04-5
Created by admin on Fri Dec 15 19:41:55 GMT 2023 , Edited by admin on Fri Dec 15 19:41:55 GMT 2023
PRIMARY