Tiotixene

Tiotixene
Clinical data

Trade names	Navane
AHFS/Drugs.com	Monograph
MedlinePlus	a682867
Pregnancy category	AU: B1
Routes of administration	Oral
ATC code	N05AF04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	10-20 hours
Identifiers
IUPAC name (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
CAS Number	5591-45-7^Y
PubChem CID	941651
IUPHAR/BPS	212
DrugBank	DB01623^Y
ChemSpider	819430^Y
UNII	7318FJ13YJ
ChEMBL	CHEMBL1201^Y
ECHA InfoCard	100.024.547
Chemical and physical data
Formula	C₂₃H₂₉N₃O₂S₂
Molar mass	443.627 g/mol
3D model (JSmol)	Interactive image
SMILES O=S(=O)(N(C)C)c2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(C)CC4
InChI 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-^Y Key:GFBKORZTTCHDGY-UWVJOHFNSA-N^Y
(verify)

Tiotixene (INN) or Thiothixene (USAN; Navane) is a typical antipsychotic drug of the thioxanthene class used in the treatment of psychoses like schizophrenia. It was introduced on July 24, 1967^[1] by Pfizer.^[2]

References

↑ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm
↑ José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 520. ISBN 3-527-31058-4.

Antipsychotics (N05A)
Typical	Benzamides Levosulpiride Sulpiride Veralipride^‡ Butyrophenones Azaperone Benperidol Bromperidol Droperidol Fluanisone Haloperidol^# Lenperone Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines Clopimozide Fluspirilene Penfluridol Pimozide Phenothiazines Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine) Chloracizine Chlorproethazine Chlorpromazine Cyamemazine Dixyrazine Fluacizine Fluphenazine Levomepromazine/Methotrimeprazine Mesoridazine Perazine Periciazine Perphenazine Perphenazine 4-aminobutyrate Piperacetazine Pipotiazine Prochlorperazine Promazine Promethazine Sulforidazine Thiethylperazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes Chlorprothixene Clopenthixol Clothixamide Flupentixol Fluprothixene Piflutixol Teflutixol Tiotixene Zuclopenthixol Tricyclics Fluotracen Loxapine Trimipramine Others Butaclamol Molindone Prothipendyl
Atypical	Benzamides Amisulpride Nemonapride Remoxipride^‡ Sultopride Tiapride Butyrophenones Cinuperone Melperone Setoperone Benzo(iso)oxazole piperidines Iloperidone Ocaperidone^§ Paliperidone Risperidone^# Benzo(iso)thiazole piperazines Lurasidone Perospirone Revospirone^§ Tiospirone^§ Ziprasidone Diphenylbutylpiperazines Amperozide Phenylpiperazines Aripiprazole Aripiprazole lauroxil Bifeprunox^§ Brexpiprazole Cariprazine Tricyclics Amoxapine Asenapine Carpipramine Clocapramine Clorotepine Clotiapine Clozapine^# Flumezapine Fluperlapine Gevotroline Metitepine Mosapramine Olanzapine Quetiapine Tenilapine Zotepine Others Blonanserin Lumateperone^† Pimavanserin RP5063^† Sertindole Zicronapine^§
Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Adrenergic receptor modulators

α₁

Agonists: 6-FNE; Amidephrine; Anisodine; Buspirone; Cirazoline; Corbadrine; Desglymidodrine; Dexisometheptene; Dipivefrine; Dopamine; Droxidopa (L-DOPS); Ephedrine; Epinephrine; Etilefrine; Etilevodopa; Ethylnorepinephrine; Indanidine; Isometheptene; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Melevodopa; Metaraminol; Methoxamine; Methyldopa; Midodrine; Naphazoline; Norepinephrine; Octopamine (drug); Oxymetazoline; Phenylephrine; Phenylpropanolamine; Pseudoephedrine; Synephrine; Tetryzoline; Tiamenidine; XP21279; Xylometazoline

Antagonists: Abanoquil; Adimolol; Ajmalicine; Alfuzosin; Amosulalol; Anisodamine; Arotinolol; Atiprosin; Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone); Benoxathian; Buflomedil; Bunazosin; Carvedilol; Corynanthine; Dapiprazole; Domesticine; Doxazosin; Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride); Etoperidone; Eugenodilol; Fenspiride; Hydroxyzine; Indoramin; Ketanserin; L-765,314; Labetalol; mCPP; Mepiprazole; Metazosin; Monatepil; Moxisylyte; Naftopidil; Nantenine; Nefazodone; Neldazosin; Niaprazine; Nicergoline; Niguldipine; Pardoprunox; Pelanserin; Phendioxan; Phenoxybenzamine; Phentolamine; Piperoxan; Prazosin; Quinazosin; Ritanserin; Silodosin; Spiperone; Talipexole; Tamsulosin; Terazosin; Tiodazosin; Tolazoline; Trazodone; Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin); Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine); Trimazosin; Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine); Urapidil; WB-4101; Zolertine

α₂

Agonists: (R)-3-Nitrobiphenyline; 4-NEMD; 6-FNE; Amitraz; Apraclonidine; Brimonidine; Cannabivarin; Clonidine; Corbadrine; Detomidine; Dexmedetomidine; Dihydroergotamine; Dipivefrine; Dopamine; Droxidopa (L-DOPS); Etilevodopa; Ephedrine; Ergotamine; Epinephrine; Etilefrine; Ethylnorepinephrine; Guanabenz; Guanfacine; Guanoxabenz; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Lofexidine; Medetomidine; Melevodopa; Methyldopa; Mivazerol; Naphazoline; Norepinephrine; Oxymetazoline; Phenylpropanolamine; Piperoxan; Pseudoephedrine; Rezatomidine; Rilmenidine; Romifidine; Talipexole; Tetrahydrozoline; Tiamenidine; Tizanidine; Tolonidine; Urapidil; XP21279; Xylazine; Xylometazoline

Antagonists: 1-PP; Adimolol; Aptazapine; Atipamezole; Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine); Azapirones (e.g., buspirone, tandospirone); BRL-44408; Buflomedil; Cirazoline; Efaroxan; Esmirtazapine; Fenmetozole; Fluparoxan; Idazoxan; mCPP; Mianserin; Mirtazapine; NAN-190; Olanzapine; Pardoprunox; Phentolamine; Phenoxybenzamine; Piperoxan; Piribedil; Rauwolscine; Rotigotine; SB-269970; Setiptiline; Spiroxatrine; Sunepitron; Tolazoline; Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine); Yohimbine

Agonists: Abediterol; Alifedrine; Amibegron; Arbutamine; Arformoterol; Arotinolol; BAAM; Bambuterol; Befunolol; Bitolterol; Broxaterol; Buphenine; Carbuterol; Carmoterol; Cimaterol; Clenbuterol; Corbadrine; Denopamine; Dipivefrine; Dobutamine; Dopamine; Dopexamine; Droxidopa (L-DOPS); Ephedrine; Epinephrine; Etafedrine; Etilefrine; Etilevodopa; Ethylnorepinephrine; Fenoterol; Formoterol; Hexoprenaline; Higenamine; Indacaterol; Isoetarine; Isoprenaline; Isoxsuprine; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Levosalbutamol; Mabuterol; Melevodopa; Methoxyphenamine; Methyldopa; Mirabegron; Norepinephrine; Orciprenaline; Oxyfedrine; PF-610355; Phenylpropanolamine; Pirbuterol; Prenalterol; Ractopamine; Procaterol; Pseudoephedrine; Reproterol; Rimiterol; Ritodrine; Salbutamol; Salmeterol; Solabegron; Terbutaline; Tretoquinol; Tulobuterol; Vilanterol; Xamoterol; XP21279; Zilpaterol; Zinterol

Antagonists: Acebutolol; Adaprolol; Adimolol; Afurolol; Alprenolol; Alprenoxime; Amosulalol; Ancarolol; Arnolol; Arotinolol; Atenolol; Befunolol; Betaxolol; Bevantolol; Bisoprolol; Bopindolol; Bornaprolol; Brefonalol; Bucindolol; Bucumolol; Bufetolol; Bufuralol; Bunitrolol; Bunolol; Bupranolol; Butaxamine; Butidrine; Butofilolol; Capsinolol; Carazolol; Carpindolol; Carteolol; Carvedilol; Celiprolol; Cetamolol; Cicloprolol; Cinamolol; Cloranolol; Cyanopindolol; Dalbraminol; Dexpropranolol; Diacetolol; Dichloroisoprenaline; Dihydroalprenolol; Dilevalol; Diprafenone; Draquinolol; Ecastolol; Epanolol; Ericolol; Ersentilide; Esatenolol; Esprolol; Eugenodilol; Exaprolol; Falintolol; Flestolol; Flusoxolol; Hydroxycarteolol; Hydroxytertatolol; ICI-118,551; Idropranolol; Indenolol; Indopanolol; Iodocyanopindolol; Iprocrolol; Isoxaprolol; Isamoltane; Labetalol; Landiolol; Levobetaxolol; Levobunolol; Levomoprolol; Medroxalol; Mepindolol; Metipranolol; Metoprolol; Moprolol; Nadolol; Nadoxolol; Nebivolol; Nifenalol; Nipradilol; Oxprenolol; Pacrinolol; Pafenolol; Pamatolol; Pargolol; Penbutolol; Pindolol; Practolol; Primidolol; Procinolol; Pronethalol; Propafenone; Propranolol; Ridazolol; Ronactolol; Soquinolol; Sotalol; Spirendolol; SR 59230A; Sulfinalol; Talinolol; Tazolol; Tertatolol; Tienoxolol; Tilisolol; Timolol; Tiprenolol; Tolamolol; Toliprolol; Xibenolol; Xipranolol

See also: Receptor/signaling modulators

Dopaminergics

Serotonergics

Monoamine reuptake inhibitors

Monoamine releasing agents

Monoamine metabolism modulators

Monoamine neurotoxins

Acetylcholine receptor modulators

Receptor modulators

mACh

Agonists: 77-LH-28-1
AC-42
AC-260,584
Aceclidine
Acetylcholine
AF30
AF150(S)
AF267B
AFDX-384
Alvameline
AQRA-741
Arecoline
Bethanechol
Butyrylcholine
Carbachol
CDD-0034
CDD-0078
CDD-0097
CDD-0098
CDD-0102
Cevimeline
Choline
cis-Dioxolane
Ethoxysebacylcholine
Itameline
LY-593,039
L-689,660
LY-2,033,298
McNA343
Methacholine
Milameline
Muscarine
NGX-267
Ocvimeline
Oxotremorine
PD-151,832
Pilocarpine
RS86
Sabcomeline
SDZ 210-086
Sebacylcholine
Suberyldicholine
Talsaclidine
Tazomeline
Thiopilocarpine
Vedaclidine
VU-0029767
VU-0090157
VU-0152099
VU-0152100
VU-0238429
WAY-132,983
Xanomeline
YM-796

Antagonists: 3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g., brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine (pyrilamine), phenindamine, pheniramine, promethazine, tripelennamine, triprolidine)
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, zotepine)
Benactyzine
Benzatropine (benztropine)
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Dimethindene
Dexetimide
DIBD
Dicyclomine (dicycloverine)
Ditran
EA-3167
EA-3443
EA-3580
EA-3834
Etanautine
Etybenzatropine (ethybenztropine)
Flavoxate
Himbacine
HL-031,120
Ipratropium bromide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Methoctramine
Metixene
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Orphenadrine
Otenzepad
Oxybutynin
PBID
PD-102,807
PD-0298029
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Procyclidine
Profenamine
Revefenacin
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Sofpironium bromide
Solifenacin
Telenzepine
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
Timepidium bromide
Tiotropium bromide
Tolterodine
Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nortriptyline, protriptyline, trimipramine)
Trihexyphenidyl
Tripitamine
Tropacine
Tropatepine
Tropicamide
Typical antipsychotics (e.g., chlorpromazine, loxapine, thioridazine)
WIN-2299
Xanomeline
Zamifenacin

nACh

Antagonists: 18-MAC
18-MC
α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others)
ABT-126
Alcuronium
Allopregnanolone
Amantadine
Anatruxonium
AQW051
Atracurium
Barbiturates (e.g., pentobarbital, sodium thiopental)
Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin)
Bupropion
Candocuronium iodide (chandonium iodide)
Chlorisondamine
Cisatracurium
Coclaurine
Coronaridine
Cyclopropane
Dacuronium bromide
Decamethonium
Dehydronorketamine
Desflurane
Dextromethorphan
Dextropropoxyphene
Dextrorphan
Diadonium
DHβE
Dihydrochandonium
Dimethyltubocurarine (metocurine)
Dipyrandium
Dizocilpine (MK-801)
Doxacurium
Encenicline
Enflurane
Esketamine
Fazadinium
Gallamine
Halothane
Hexafluronium
Hexamethonium (benzohexonium)
Hydroxybupropion
Hydroxynorketamine
Ibogaine
Isoflurane
Ketamine
Kynurenic acid
Laudexium (laudolissin)
Levacetylmethadol
Levomethadone
Malouetine
ME-18-MC
Mecamylamine
Memantine
Methadone
Methorphan (racemethorphan)
Methyllycaconitine
Metocurine
Mivacurium
Morphanol (racemorphan)
Neramexane
Nitrous oxide
Norketamine
Pancuronium bromide
Pempidine
Pentamine
Pentolinium
Phencyclidine
Pipecuronium bromide
Progesterone
Promegestone
Radafaxine
Rapacuronium bromide
Reboxetine
Rocuronium bromide
Sevoflurane
Stercuronium iodide
Surugatoxin
Thiocolchicoside
Toxiferine
Tramadol
Trimetaphan camsilate (trimethaphan camsylate)
Tropeinium
Tubocurarine
Vanoxerine
Vecuronium bromide
Xenon

Transporter modulators

CHT	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChT	Inhibitors: Vesamicol

Enzyme modulators

ChAT	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChE	Inhibitors: Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Caffeine Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Itopride Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Distigmine bromide Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine bromide Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Donepezil Caffeine Edrophonium Galantamine Huperzine A Ipidacrine Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Anatoxin-a(S) Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Cyclosarin Demeton Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Unsorted: Stercuronium iodide Reactivators: Asoxime Obidoxime Pralidoxime
BChE	Inhibitors: Cymserine Many of the AChE inhibitors listed above

Release modulators

Inhibitors	SNAP-25 inactivators: Botulinum toxin (A, C, E) VAMP inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHN agonists: α-Latrotoxin Others: Atracotoxin (e.g., robustoxin, versutoxin) Crotoxin

Others

Precursors / prodrugs	Adafenoxate Choline (lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol
Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅

See also: Receptor/signaling modulators

Dopamine receptor modulators

D₁-like

Agonists

Benzazepines 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam
Ergolines Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride
Dihydrexidine derivatives A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine
Phenethylamines BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279
Others A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tetrahydropalmatine

Antagonists

Typical antipsychotics Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol
Atypical antipsychotics Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (++fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine
Others Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam SCH-23390

D₂-like