THIOTHIXENE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29N3O2S2.2ClH.2H2O
Molecular Weight	552.578
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MEUAAEMCZUPORO-LRSHZYOCSA-N

InChI=1S/C23H29N3O2S2.2ClH.2H2O/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;2*1H2/b19-8-;;;;

HIDE SMILES / InChI

Molecular Formula	C23H29N3O2S2
Molecular Weight	443.625
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1145194 | (1977) Annual Reports in Medicinal Chemistry, v.12, page 255, retrieved from: https://books.google.ru/books?id=1KgRHPGu7LEC | https://www.ncbi.nlm.nih.gov/pubmed/7161337https://www.drugs.com/ppa/thiothixene.html
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
dopamine secretion 11 Target ID: GO:0014046 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1145194	Inhibitor 8297
Dopamine receptor 60 Target ID: CHEMBL2096970 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1060143	Binding Agent 1064	22.0 µM [IC50]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://www.genome.jp/dbget-bin/www_bget?D00374+D02612 \| https://www.drugbank.ca/drugs/DB01623#targets	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.pfizer.com/files/products/uspi_navane.pdf	Primary		Approved 8429	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
Unknown 2578

C_max

Value	Dose	Co-administered	Analyte	Population
27.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447478	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

Value	Dose	Co-administered	Analyte	Population
117 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447478	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9447478	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	Disc. AE: Hyperprolactinemia, Menstrual irregularity... AEs leading to discontinuation/dose reduction: Hyperprolactinemia Menstrual irregularity Breast enlargement Amenorrhea Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	Disc. AE: Tardive dyskinesia, Neutropenia... AEs leading to discontinuation/dose reduction: Tardive dyskinesia Neutropenia (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf	unhealthy Health Status: unhealthy Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/016584s059lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1054

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://dmd.aspetjournals.org/content/27/9/1078.long	yes [Ki 65 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4336924/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-055249	http://www.3bsc.com/index/pro_info.php?id=93728
AA Blocks	AA003APY	https://www.aablocks.com/goods/Goods/detail?id=AA003APY
AHH Chemical co.,ltd	MT-49407	http://www.ahhchemical.com/product/MT-49407.html
Alfa Chemistry	AP3313266	https://reagents.alfa-chemistry.com/product/thiothixene-cas-3313-26-6-10093.html
Aurora Fine Chemicals LLC	A17.877.865	http://online.aurorafinechemicals.com/info?ID=A17.877.865
BLD Pharm	BD121796	http://www.bldpharm.com/products/3313-26-6.html
CSNpharm	CSN21566	https://www.csnpharm.com/products/(z)-thiothixene.html
Chem Scene	CS-7959	http://www.chemscene.com/3313-26-6.html
ChemMol	49411943	http://www.chemmol.com/chemmol/49411943.html
ChemMol	99082728	http://www.chemmol.com/chemmol/99082728.html
Chemspace	CSSB00020677860	https://chem-space.com/CSSB00020677860
LGC Standards	LGCFOR3269.00	https://www.lgcstandards.com/US/en/p/LGCFOR3269.00
LGC Standards	MM3269.00	https://www.lgcstandards.com/US/en/p/MM3269.00
Lab Network	LN01312553	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01312553
MedChem Express	HY-108324	https://www.medchemexpress.com/_Z_-Thiothixene.html
Sigma-Aldrich	T4937_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t4937?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1665003_USP	https://www.sigmaaldrich.com/catalog/product/usp/1665003?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S545259	http://www.smolecule.com/products/s545259
Smolecule	S583328	https://www.smolecule.com/products/s583328
THE BioTek	bt-284641	https://www.thebiotek.com/product/inhibitors/bt-284641
THE BioTek	bt-292946	https://www.thebiotek.com/product/others/bt-292946
Tyger Scientific	T15560	http://www.tygersci.com/phtml/3313-26-6.htm
abcr GmbH	AB154516	http://www.abcr.com/shop/en/AB154516
eNovation Chemicals	D590248	https://www.enovationchem.com/ProductDetails.asp?ProductID=D590248

PubMed

Title	Date	PubMed
Benztropine prophylaxis of dystonic reactions.	1979 Mar 28	36644
Motility, Parkinsonism, and prolactin with thiothixene and thioridazine.	1981 Jun	7247630
Thiothixene plasma levels and clinical response in acute schizophrenia.	1981 May	7217026
Separation and quantitation of cis- and trans-thiothixene in human plasma by high-performance liquid chromatography.	1982 Dec 10	7161337
Neurotoxicity in patients with schizophrenia during lithium therapy.	1982 May-Jun	6123407
Akathisia with haloperidol and thiothixene.	1984 Nov	6497564
Improved high-performance liquid chromatographic method for the quantitation of cis-thiothixene in plasma samples using trans-thiothixene as internal standard.	1984 Nov 28	6520191
Rapid tranquilization: a comparison of thiothixene with loxapine.	1986 Jun	3711026
On the selection of mice for haloperidol response and non-response.	1991	1827527
Esophageal atony and dilatation as a side effect of thiothixene and benztropine.	1993 Jul	8354511
Neuroleptic-induced extrapyramidal side effects.	1993 Nov	8214193
Fluoxetine and visual hallucinations in dementia.	1995 Oct 15	8562668
Metabolites of the antipsychotic agent clozapine inhibit the replication of human immunodeficiency virus type 1.	1997 May 3	9176928
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.	2003 Mar	12629531
Density functional theory study of structural and electronic properties of trans and cis structures of thiothixene as a nano-drug.	2017 Nov 25	29177682

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:14:27 GMT 2023` Edited by `admin` on `Fri Dec 15 15:14:27 GMT 2023`
Record UNII	B3CRJ1EWJU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOTHIXENE HYDROCHLORIDE

Official Name

English

THIOTHIXENE HCL H20

Common Name

English

THIOTHIXENE HYDROCHLORIDE [USP IMPURITY]

Common Name

English

TIOTIXENE HYDROCHLORIDE [MART.]

Common Name

English

THIOTHIXENE HYDROCHLORIDE [USAN]

Common Name

English

CP-12,252-1

Code

English

CP-122521

Code

English

9H-THIOXANTHENE-2-SULFONAMIDE, N,N-DIMETHYL-9-(3-(4-METHYL-1-PIPERAZINYL)PROPYLIDENE)-, DIHYDROCHLORIDE, DIHYDRATE (Z)-

Systematic Name

English

THIOTHIXENE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

N,N-Dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]thioxanthene-2-sulfonamide dihydrochloride dihydrate

Systematic Name

English

THIOTHIXENE HYDROCHLORIDE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710