Identification

Name
Thioproperazine
Accession Number
DB01622
Type
Small Molecule
Groups
Approved
Description

Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property. It is used for the treatment of all types of acute and chronic schizophrenia, including those which did not respond to the usual neuroleptics; manic syndromes. Overdosage may result in severe extrapyramidal symptoms with dysphagia, marked sialorrhea, persistent and rapidly increasing hyperthermia, pulmonary syndrome, state of shock with pallor and profuse sweating, which may be followed by collapse and coma. LD50 in mice is 70 mg/kg I.V., 120 mg/kg I.P., 500 mg/kg S.C. and 830 mg/kg P.O.

Structure
Thumb
Synonyms
  • (Thioproperazine)-2-dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine
  • 2-Dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine
  • N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine-2-sulfonamide
  • N,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine-2-sulfonamide
  • Thioperazine
  • Thioproperazin
  • Thioproperazinum
  • Tioproferazina
  • Tioproperazina
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Majeptil Tab 10mgTablet10 mgOralErfa Canada 2012 Inc1962-12-31Not applicableCanada
International/Other Brands
Majeptil
Categories
UNII
YJ050AQ56X
CAS number
316-81-4
Weight
Average: 446.629
Monoisotopic: 446.181017604
Chemical Formula
C22H30N4O2S2
InChI Key
VZYCZNZBPPHOFY-UHFFFAOYSA-N
InChI
InChI=1S/C22H30N4O2S2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17H,6,11-16H2,1-3H3
IUPAC Name
N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide
SMILES
CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1

Pharmacology

Indication

For the treatment of all types of acute and chronic schizophrenia, including those which did not respond to the usual neuroleptics; manic syndromes.

Structured Indications
Pharmacodynamics

Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property.

Mechanism of action

Thioproperazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects).

TargetActionsOrganism
AD(2) dopamine receptor
antagonist
Human
UD(1A) dopamine receptor
antagonist
Human
A5-hydroxytryptamine receptor 2A
antagonist
Human
A5-hydroxytryptamine receptor 1A
antagonist
Human
AAlpha-1A adrenergic receptor
antagonist
Human
AAlpha-1B adrenergic receptor
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Overdosage may result in severe extrapyramidal symptoms with dysphagia, marked sialorrhea, persistent and rapidly increasing hyperthermia, pulmonary syndrome, state of shock with pallor and profuse sweating, which may be followed by collapse and coma. LD50 in mice is 70 mg/kg I.V., 120 mg/kg I.P., 500 mg/kg S.C. and 830 mg/kg P.O.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineThioproperazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.Experimental, Illicit
3,4-MethylenedioxyamphetamineThioproperazine may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineThioproperazine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.Experimental, Illicit
5'-Deoxy-5'-MethylthioadenosineThe serum concentration of Thioproperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Experimental
AcebutololThioproperazine may increase the hypotensive activities of Acebutolol.Approved
AlaproclateThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Alaproclate.Experimental
AlfentanilThioproperazine may increase the hypotensive activities of Alfentanil.Approved, Illicit
AlgeldrateAlgeldrate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Experimental
AlmagateAlmagate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
AlmasilateAlmasilate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Experimental
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Thioproperazine.Approved, Investigational
AloglutamolAloglutamol can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
AlphacetylmethadolThioproperazine may increase the hypotensive activities of Alphacetylmethadol.Experimental, Illicit
AlphaprodineThioproperazine may increase the hypotensive activities of Alphaprodine.Illicit
AlprenololThioproperazine may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AluminiumAluminium can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Aluminium acetoacetateAluminium acetoacetate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
Aluminium glycinateAluminium glycinate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
AmantadineThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Amantadine.Approved
AmisulprideThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Thioproperazine.Approved
AmodiaquineThe serum concentration of Thioproperazine can be increased when it is combined with Amodiaquine.Approved, Investigational
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Thioproperazine.Approved
AmphetamineThioproperazine may decrease the stimulatory activities of Amphetamine.Approved, Illicit
ApomorphineThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Apomorphine.Approved, Investigational
ArotinololThioproperazine may increase the hypotensive activities of Arotinolol.Approved, Investigational
ArtemetherThe serum concentration of Thioproperazine can be increased when it is combined with Artemether.Approved
ArtemisininThe serum concentration of Thioproperazine can be increased when it is combined with Artemisinin.Investigational
ArtemotilThe serum concentration of Thioproperazine can be increased when it is combined with Artemotil.Experimental
ArtenimolThe serum concentration of Thioproperazine can be increased when it is combined with Artenimol.Approved, Investigational
ArtesunateThe serum concentration of Thioproperazine can be increased when it is combined with Artesunate.Approved, Investigational
AtenololThioproperazine may increase the hypotensive activities of Atenolol.Approved
AtovaquoneThe serum concentration of Thioproperazine can be increased when it is combined with Atovaquone.Approved
BefunololThioproperazine may increase the hypotensive activities of Befunolol.Experimental
BenzphetamineThioproperazine may decrease the stimulatory activities of Benzphetamine.Approved, Illicit
BetaxololThioproperazine may increase the hypotensive activities of Betaxolol.Approved
BevantololThioproperazine may increase the hypotensive activities of Bevantolol.Approved
BezitramideThioproperazine may increase the hypotensive activities of Bezitramide.Experimental, Illicit, Withdrawn
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Bismuth subnitrateBismuth subnitrate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
BisoprololThioproperazine may increase the hypotensive activities of Bisoprolol.Approved
BopindololThioproperazine may increase the hypotensive activities of Bopindolol.Approved
BromocriptineThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Bromocriptine.Approved, Investigational
BucindololThioproperazine may increase the hypotensive activities of Bucindolol.Investigational
BufuralolThioproperazine may increase the hypotensive activities of Bufuralol.Experimental, Investigational
BupranololThioproperazine may increase the hypotensive activities of Bupranolol.Approved
BuprenorphineThioproperazine may increase the hypotensive activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Thioproperazine.Approved, Investigational
ButorphanolThioproperazine may increase the hypotensive activities of Butorphanol.Approved, Illicit, Vet Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Thioproperazine.Approved
Calcium CarbonateCalcium Carbonate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium silicateCalcium silicate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
CarfentanilThioproperazine may increase the hypotensive activities of Carfentanil.Illicit, Investigational, Vet Approved
CarteololThioproperazine may increase the hypotensive activities of Carteolol.Approved
CarvedilolThioproperazine may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololThioproperazine may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChloroquineThe serum concentration of Thioproperazine can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorphentermineThioproperazine may decrease the stimulatory activities of Chlorphentermine.Illicit, Withdrawn
ChlorproguanilThe serum concentration of Thioproperazine can be increased when it is combined with Chlorproguanil.Investigational
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Thioproperazine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Thioproperazine.Approved, Vet Approved
CloranololThioproperazine may increase the hypotensive activities of Cloranolol.Experimental
CodeineThioproperazine may increase the hypotensive activities of Codeine.Approved, Illicit
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Thioproperazine.Approved
Cycloguanil embonateThe serum concentration of Thioproperazine can be increased when it is combined with Cycloguanil embonate.Experimental
DapoxetineThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Dapoxetine.Investigational
DapsoneThe serum concentration of Thioproperazine can be increased when it is combined with Dapsone.Approved, Investigational
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Thioproperazine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Thioproperazine.Approved
DextroamphetamineThioproperazine may decrease the stimulatory activities of Dextroamphetamine.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Thioproperazine.Approved
DextromoramideThioproperazine may increase the hypotensive activities of Dextromoramide.Experimental, Illicit
DextropropoxypheneThioproperazine may increase the hypotensive activities of Dextropropoxyphene.Approved, Illicit, Investigational, Withdrawn
DezocineThioproperazine may increase the hypotensive activities of Dezocine.Approved, Investigational
DiethylpropionThioproperazine may decrease the stimulatory activities of Diethylpropion.Approved, Illicit
DihydrocodeineThioproperazine may increase the hypotensive activities of Dihydrocodeine.Approved, Illicit
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Thioproperazine.Approved
DihydroetorphineThioproperazine may increase the hypotensive activities of Dihydroetorphine.Experimental, Illicit
DihydromorphineThioproperazine may increase the hypotensive activities of Dihydromorphine.Experimental, Illicit
DiphenoxylateThioproperazine may increase the hypotensive activities of Diphenoxylate.Approved, Illicit
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Thioproperazine.Approved
DoxycyclineThe serum concentration of Thioproperazine can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DPDPEThioproperazine may increase the hypotensive activities of DPDPE.Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Thioproperazine.Approved
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Thioproperazine.Approved, Investigational
EpanololThioproperazine may increase the hypotensive activities of Epanolol.Experimental
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Thioproperazine.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Thioproperazine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Thioproperazine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Thioproperazine.Approved, Investigational
EsmololThioproperazine may increase the hypotensive activities of Esmolol.Approved
EthylmorphineThioproperazine may increase the hypotensive activities of Ethylmorphine.Approved, Illicit
EtorphineThioproperazine may increase the hypotensive activities of Etorphine.Illicit, Vet Approved
FenfluramineThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Fenfluramine.Illicit, Investigational, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Thioproperazine.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Thioproperazine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Thioproperazine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Thioproperazine.Approved, Investigational
GepefrineThioproperazine may decrease the stimulatory activities of Gepefrine.Experimental
HalofantrineThe serum concentration of Thioproperazine can be increased when it is combined with Halofantrine.Approved
HeroinThioproperazine may increase the hypotensive activities of Heroin.Approved, Illicit, Investigational
HydrocodoneThioproperazine may increase the hypotensive activities of Hydrocodone.Approved, Illicit
HydromorphoneThioproperazine may increase the hypotensive activities of Hydromorphone.Approved, Illicit
HydrotalciteHydrotalcite can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental, Investigational
HydroxyamphetamineThioproperazine may decrease the stimulatory activities of Hydroxyamphetamine.Approved
HydroxychloroquineThe serum concentration of Thioproperazine can be increased when it is combined with Hydroxychloroquine.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Thioproperazine.Approved
IndalpineThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Indalpine.Investigational, Withdrawn
IndenololThioproperazine may increase the hypotensive activities of Indenolol.Withdrawn
Iofetamine I-123Thioproperazine may decrease the stimulatory activities of Iofetamine I-123.Approved
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Thioproperazine.Approved
KetobemidoneThioproperazine may increase the hypotensive activities of Ketobemidone.Approved, Investigational
LabetalolThioproperazine may increase the hypotensive activities of Labetalol.Approved
LandiololThioproperazine may increase the hypotensive activities of Landiolol.Investigational
LevobunololThioproperazine may increase the hypotensive activities of Levobunolol.Approved
LevodopaThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Levodopa.Approved
Levomethadyl AcetateThioproperazine may increase the hypotensive activities of Levomethadyl Acetate.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Thioproperazine.Approved
LevorphanolThioproperazine may increase the hypotensive activities of Levorphanol.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Thioproperazine.Approved, Investigational
LisdexamfetamineThioproperazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Thioproperazine.Approved
LofentanilThioproperazine may increase the hypotensive activities of Lofentanil.Illicit
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Thioproperazine.Approved
LumefantrineThe serum concentration of Thioproperazine can be increased when it is combined with Lumefantrine.Approved
MagaldrateMagaldrate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Withdrawn
Magnesium HydroxideMagnesium Hydroxide can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium peroxideMagnesium peroxide can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
Magnesium silicateMagnesium silicate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Experimental
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Thioproperazine.Approved
MefloquineThe serum concentration of Thioproperazine can be increased when it is combined with Mefloquine.Approved
MephedroneThioproperazine may decrease the stimulatory activities of Mephedrone.Investigational
MephentermineThioproperazine may decrease the stimulatory activities of Mephentermine.Approved
MepindololThioproperazine may increase the hypotensive activities of Mepindolol.Experimental
MeptazinolThioproperazine may increase the hypotensive activities of Meptazinol.Experimental
MequitazineThioproperazine may increase the arrhythmogenic activities of Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Thioproperazine.Approved
Methadyl AcetateThioproperazine may increase the hypotensive activities of Methadyl Acetate.Approved, Illicit
MethamphetamineThioproperazine may decrease the stimulatory activities of Methamphetamine.Approved, Illicit
MethoxyphenamineThioproperazine may decrease the stimulatory activities of Methoxyphenamine.Experimental
MethylphenidateThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Methylphenidate.Approved, Investigational
MetipranololThioproperazine may increase the hypotensive activities of Metipranolol.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Thioproperazine.Approved, Investigational
MetoprololThioproperazine may increase the hypotensive activities of Metoprolol.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Thioproperazine.Approved
MidomafetamineThioproperazine may decrease the stimulatory activities of Midomafetamine.Experimental, Illicit, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Thioproperazine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Thioproperazine.Approved
MizoribineThe serum concentration of Thioproperazine can be increased when it is combined with Mizoribine.Investigational
MMDAThioproperazine may decrease the stimulatory activities of MMDA.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Thioproperazine.Approved
MorphineThioproperazine may increase the hypotensive activities of Morphine.Approved, Investigational
NadololThioproperazine may increase the hypotensive activities of Nadolol.Approved
NalbuphineThioproperazine may increase the hypotensive activities of Nalbuphine.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Thioproperazine.Approved, Investigational
NebivololThioproperazine may increase the hypotensive activities of Nebivolol.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Thioproperazine.Approved, Withdrawn
NicomorphineThioproperazine may increase the hypotensive activities of Nicomorphine.Experimental
NormethadoneThioproperazine may increase the hypotensive activities of Normethadone.Approved, Illicit
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Thioproperazine.Approved
OlanzapineThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Olanzapine.Approved, Investigational
OpiumThioproperazine may increase the hypotensive activities of Opium.Approved, Illicit
OxprenololThioproperazine may increase the hypotensive activities of Oxprenolol.Approved
OxycodoneThioproperazine may increase the hypotensive activities of Oxycodone.Approved, Illicit, Investigational
OxymorphoneThioproperazine may increase the hypotensive activities of Oxymorphone.Approved, Investigational, Vet Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Thioproperazine.Approved, Investigational
PenbutololThioproperazine may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentazocineThioproperazine may increase the hypotensive activities of Pentazocine.Approved, Vet Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Thioproperazine.Approved
PhenazocineThioproperazine may increase the hypotensive activities of Phenazocine.Experimental
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Thioproperazine.Approved
PhenoperidineThioproperazine may increase the hypotensive activities of Phenoperidine.Experimental
PhentermineThioproperazine may decrease the stimulatory activities of Phentermine.Approved, Illicit
PindololThioproperazine may increase the hypotensive activities of Pindolol.Approved
PiribedilThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Piribedil.Investigational
PiritramideThioproperazine may increase the hypotensive activities of Piritramide.Investigational
Platelet Activating FactorThioproperazine may increase the hypotensive activities of Platelet Activating Factor.Experimental
PractololThioproperazine may increase the hypotensive activities of Practolol.Approved
PramipexoleThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Pramipexole.Approved, Investigational
PrimaquineThe serum concentration of Thioproperazine can be increased when it is combined with Primaquine.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Thioproperazine.Approved
ProguanilThe serum concentration of Thioproperazine can be increased when it is combined with Proguanil.Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Thioproperazine.Approved
PropranololThioproperazine may increase the hypotensive activities of Propranolol.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Thioproperazine.Approved
PseudoephedrineThioproperazine may decrease the stimulatory activities of Pseudoephedrine.Approved
PyrimethamineThe serum concentration of Thioproperazine can be increased when it is combined with Pyrimethamine.Approved, Vet Approved
PyronaridineThe serum concentration of Thioproperazine can be increased when it is combined with Pyronaridine.Investigational
QuinacrineThe serum concentration of Thioproperazine can be increased when it is combined with Quinacrine.Approved, Investigational
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Thioproperazine.Approved
QuinidineThe serum concentration of Thioproperazine can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Thioproperazine can be increased when it is combined with Quinine.Approved
RadicicolThe serum concentration of Thioproperazine can be increased when it is combined with Radicicol.Experimental
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Thioproperazine.Approved
RemifentanilThioproperazine may increase the hypotensive activities of Remifentanil.Approved
RitobegronThioproperazine may decrease the stimulatory activities of Ritobegron.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Thioproperazine.Approved
RopiniroleThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Ropinirole.Approved, Investigational
RotigotineThe therapeutic efficacy of Thioproperazine can be decreased when used in combination with Rotigotine.Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Thioproperazine.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Thioproperazine.Approved
SinefunginThe serum concentration of Thioproperazine can be increased when it is combined with Sinefungin.Experimental
Sodium bicarbonateSodium bicarbonate can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SotalolThioproperazine may increase the hypotensive activities of Sotalol.Approved
SufentanilThioproperazine may increase the hypotensive activities of Sufentanil.Approved, Investigational
SulfadoxineThe serum concentration of Thioproperazine can be increased when it is combined with Sulfadoxine.Approved, Investigational
SulfametopyrazineThe serum concentration of Thioproperazine can be increased when it is combined with Sulfametopyrazine.Approved, Withdrawn
SulpirideThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Sulpiride.Approved, Investigational
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Thioproperazine.Approved, Investigational
tafenoquineThe serum concentration of Thioproperazine can be increased when it is combined with tafenoquine.Investigational
TalinololThioproperazine may increase the hypotensive activities of Talinolol.Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Thioproperazine.Approved
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Thioproperazine.Approved
TertatololThioproperazine may increase the hypotensive activities of Tertatolol.Experimental
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Thioproperazine.Approved
ThiopentalThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Thiopental.Approved, Vet Approved
TilidineThioproperazine may increase the hypotensive activities of Tilidine.Experimental
TimololThioproperazine may increase the hypotensive activities of Timolol.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Thioproperazine.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Thioproperazine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Thioproperazine.Approved, Investigational
TrimethoprimThe serum concentration of Thioproperazine can be increased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Thioproperazine.Approved
TromethamineTromethamine can cause a decrease in the absorption of Thioproperazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Thioproperazine.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Thioproperazine.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Thioproperazine.Approved
ZimelidineThe risk or severity of adverse effects can be increased when Thioproperazine is combined with Zimelidine.Withdrawn
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Thioproperazine.Approved, Investigational
Food Interactions
  • Avoid alcohol
  • Take with food to avoid irritation

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15559
KEGG Drug
D08585
PubChem Compound
9429
PubChem Substance
46507111
ChemSpider
9058
BindingDB
81793
ChEBI
59120
ChEMBL
CHEMBL609109
PharmGKB
PA164754875
ATC Codes
N05AB08 — Thioproperazine
AHFS Codes
  • 28:16.08.24 — Phenothiazines

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedNot AvailableBipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral10 mg
Prices
Unit descriptionCostUnit
Majeptil 10 mg Tablet0.6USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0569 mg/mLALOGPS
logP3.09ALOGPS
logP2.83ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.1 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.95 m3·mol-1ChemAxon
Polarizability49.62 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier+0.9629
Caco-2 permeable-0.6568
P-glycoprotein substrateSubstrate0.7908
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.7979
Renal organic cation transporterNon-inhibitor0.5396
CYP450 2C9 substrateNon-substrate0.7704
CYP450 2D6 substrateNon-substrate0.8194
CYP450 3A4 substrateSubstrate0.5366
CYP450 1A2 substrateNon-inhibitor0.8243
CYP450 2C9 inhibitorNon-inhibitor0.8758
CYP450 2D6 inhibitorInhibitor0.6293
CYP450 2C19 inhibitorNon-inhibitor0.7713
CYP450 3A4 inhibitorInhibitor0.6338
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6663
Ames testNon AMES toxic0.7056
CarcinogenicityNon-carcinogens0.8109
BiodegradationNot ready biodegradable0.9934
Rat acute toxicity2.6623 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7265
hERG inhibition (predictor II)Non-inhibitor0.5303
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-01vo-9411000000-e918c0715fd27f21a62f
GC-MS Spectrum - EI-BGC-MSsplash10-0229-6924100000-fcb76747a5faaee6b722
GC-MS Spectrum - CI-BGC-MSsplash10-0002-1001900000-0b26a1120865f1ac9f3a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / N-methylpiperazines / Organosulfonamides / Benzenoids / 1,4-thiazines / Aminosulfonyl compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / N-methylpiperazine / N-alkylpiperazine / Para-thiazine / 1,4-diazinane / Piperazine
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, sulfonamide, N-alkylpiperazine, N-methylpiperazine (CHEBI:59120)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [PubMed:11103886]
  2. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706]
  3. Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [PubMed:15694263]
  4. Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [PubMed:16867246]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [PubMed:20643630]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [PubMed:7918347]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [PubMed:10821438]
  2. Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. [PubMed:8593484]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. [PubMed:11755134]
  2. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. [PubMed:9760039]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Kitamura K, Omran AA, Nagata C, Kamijima Y, Tanaka R, Takegami S, Kitade T: Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):972-6. [PubMed:16819214]
  2. Rukhadze MD, Bezarashvili GS, Sidamonidze NS, Tsagareli SK: Investigation of binding process of chlorpromazine to bovine serum albumin by means of passive and active experiments. Biomed Chromatogr. 2001 Oct;15(6):365-73. [PubMed:11559920]
  3. Silva D, Cortez CM, Louro SR: Quenching of the intrinsic fluorescence of bovine serum albumin by chlorpromazine and hemin. Braz J Med Biol Res. 2004 Jul;37(7):963-8. Epub 2004 Jun 22. [PubMed:15264002]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755]

Drug created on August 29, 2007 14:17 / Updated on November 19, 2017 20:34