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Identification
NamePropericiazine
Accession NumberDB01608
TypeSmall Molecule
GroupsApproved
DescriptionPropericiazine is a phenothiazine of the piperidine group. It has been shown to reduce pathologic arousal and affective tension in some psychotic patients, while the symptoms of abnormal mental integration are relatively unaffected. It is a sedative phenothiazine with weak antipsychotic properties. It also has adrenolytic, anticholinergic, metabolic and endocrine effects and an action on the extrapyramidal system. It is used as an adjunctive medication in some psychotic patients, for the control of residual prevailing hostility, impulsiveness and aggressiveness. Pericyazine, like other phenothiazines, is presumed to act principally in the subcortical areas, by producing what has been described as a central adrenergic blockade.
Structure
Thumb
Synonyms
10-(3-(4-Hydroxypiperidino)propyl)phenothiazine-2-carbonitrile
2-Cyano-10-(3-(4-hydroxy-1-piperidyl)propyl)phenothiazine
2-Cyano-10-(3-(4-hydroxypiperidino)propyl)phenothiazine
Cyano-3 ((hydroxy-4 piperidyl-1)-3 propyl)-10 phenothiazine
Periciazina
Periciazine
Periciazinum
Pericyazine
Piperocyanomazine
Propericiazine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Neuleptil 10mg CapsulesCapsule10 mgOralErfa Canada 2012 Inc1969-12-31Not applicableCanada
Neuleptil 20mg CapsulesCapsule20 mgOralErfa Canada 2012 Inc1976-12-31Not applicableCanada
Neuleptil 5mg CapsulesCapsule5 mgOralErfa Canada 2012 Inc1969-12-31Not applicableCanada
Neuleptil Gouttes 10mg/mlSolution / drops10 mgOralErfa Canada 2012 Inc1976-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NeulactilNot Available
NeuleptilNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3405M6FD73
CAS number2622-26-6
WeightAverage: 365.492
Monoisotopic: 365.156183063
Chemical FormulaC21H23N3OS
InChI KeyLUALIOATIOESLM-UHFFFAOYSA-N
InChI
InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2
IUPAC Name
10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile
SMILES
OC1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C#N)CC1
Pharmacology
IndicationFor use as adjunctive medication in some psychotic patients. Propericiazine (Pericyazine)is used for the control of residual prevailing hostility, impulsiveness and aggressiveness.
Structured Indications
PharmacodynamicsPericyazine is a phenothiazine of the piperidine group. It has been shown to reduce pathologic arousal and affective tension in some psychotic patients, while the symptoms of abnormal mental integration are relatively unaffected. It is a sedative phenothiazine with weak antipsychotic properties. It also has adrenolytic, anticholinergic, metabolic and endocrine effects, and an action on the extrapyramidal system.
Mechanism of actionPericyazine, like other phenothiazines, is presumed to act principally in the subcortical areas, by producing what has been described as a central adrenergic blockade of the alpha adrenergic receptors as well as antagonism of the D(1) dopamine receptor.
TargetKindPharmacological actionActionsOrganismUniProt ID
D(1A) dopamine receptorProteinyes
antagonist
HumanP21728 details
Alpha-2A adrenergic receptorProteinyes
antagonist
HumanP08913 details
Alpha-1B adrenergic receptorProteinunknown
antagonist
HumanP35368 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityIn milder cases of phenothiazine overdosage the patient may be agitated, delirious and confused. Frequently he is lethargic or in a comatose state. Twitching, dystonic movements or convulsions may be present and hypotension, cardiovascular collapse, arrhythmias and hypothermia might be observed.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetaminePropericiazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.Experimental, Illicit
3,4-MethylenedioxyamphetaminePropericiazine may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.Experimental, Illicit
3,4-MethylenedioxymethamphetaminePropericiazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetaminePropericiazine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.Experimental, Illicit
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Propericiazine.Approved, Investigational
AmantadineThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Amantadine.Approved
AmisulprideThe risk or severity of adverse effects can be increased when Propericiazine is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Propericiazine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Propericiazine.Approved
AmphetaminePropericiazine may decrease the stimulatory activities of Amphetamine.Approved, Illicit
ApomorphineThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Apomorphine.Approved, Investigational
BenzphetaminePropericiazine may decrease the stimulatory activities of Benzphetamine.Approved, Illicit
BromocriptineThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Bromocriptine.Approved, Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Propericiazine.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Propericiazine.Approved
ChlorphenterminePropericiazine may decrease the stimulatory activities of Chlorphentermine.Illicit, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Propericiazine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Propericiazine.Approved, Vet Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Propericiazine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Propericiazine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Propericiazine.Approved
DextroamphetaminePropericiazine may decrease the stimulatory activities of Dextroamphetamine.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Propericiazine.Approved
DiethylpropionPropericiazine may decrease the stimulatory activities of Diethylpropion.Approved, Illicit
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Propericiazine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Propericiazine.Approved
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Propericiazine.Approved
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Propericiazine.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Propericiazine.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Propericiazine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Propericiazine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Propericiazine.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Propericiazine.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Propericiazine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Propericiazine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Propericiazine.Approved, Investigational
Hydroxyamphetamine hydrobromidePropericiazine may decrease the stimulatory activities of Hydroxyamphetamine hydrobromide.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Propericiazine.Approved
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Propericiazine.Approved
LevodopaThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Levodopa.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Propericiazine.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Propericiazine.Approved, Investigational
LisdexamfetaminePropericiazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Propericiazine.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Propericiazine.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Propericiazine.Approved
MephedronePropericiazine may decrease the stimulatory activities of Mephedrone.Investigational
MephenterminePropericiazine may decrease the stimulatory activities of Mephentermine.Approved
MequitazinePropericiazine may increase the arrhythmogenic activities of Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Propericiazine.Approved
MethamphetaminePropericiazine may decrease the stimulatory activities of Methamphetamine.Approved, Illicit
MethylphenidateThe risk or severity of adverse effects can be increased when Propericiazine is combined with Methylphenidate.Approved, Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Propericiazine.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Propericiazine.Approved
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Propericiazine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Propericiazine.Approved
MMDAPropericiazine may decrease the stimulatory activities of MMDA.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Propericiazine.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Propericiazine.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Propericiazine.Approved, Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Propericiazine.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Propericiazine.Approved, Investigational
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Propericiazine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Propericiazine.Approved
PhenterminePropericiazine may decrease the stimulatory activities of Phentermine.Approved, Illicit
PiribedilThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Piribedil.Investigational
PramipexoleThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Pramipexole.Approved, Investigational
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Propericiazine.Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Propericiazine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Propericiazine.Approved
PseudoephedrinePropericiazine may decrease the stimulatory activities of Pseudoephedrine.Approved
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Propericiazine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Propericiazine.Approved
RitobegronPropericiazine may decrease the stimulatory activities of Ritobegron.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Propericiazine.Approved
RopiniroleThe therapeutic efficacy of Propericiazine can be decreased when used in combination with Ropinirole.Approved, Investigational
RotigotineThe therapeutic efficacy of Propericiazine 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 Propericiazine.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Propericiazine.Approved
SulpirideThe risk or severity of adverse effects can be increased when Propericiazine is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Propericiazine.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Propericiazine.Approved
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Propericiazine.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Propericiazine.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Propericiazine.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Propericiazine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Propericiazine.Approved, Investigational
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Propericiazine.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Propericiazine.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Propericiazine.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Propericiazine.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Propericiazine.Approved, Investigational
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesN05AC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9747
Blood Brain Barrier+0.9691
Caco-2 permeable+0.5608
P-glycoprotein substrateSubstrate0.6582
P-glycoprotein inhibitor IInhibitor0.8072
P-glycoprotein inhibitor IIInhibitor0.6046
Renal organic cation transporterInhibitor0.6545
CYP450 2C9 substrateNon-substrate0.7657
CYP450 2D6 substrateSubstrate0.6233
CYP450 3A4 substrateNon-substrate0.6064
CYP450 1A2 substrateInhibitor0.6843
CYP450 2C9 inhibitorNon-inhibitor0.8852
CYP450 2D6 inhibitorInhibitor0.6558
CYP450 2C19 inhibitorNon-inhibitor0.8539
CYP450 3A4 inhibitorNon-inhibitor0.8952
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7203
Ames testNon AMES toxic0.6802
CarcinogenicityNon-carcinogens0.9537
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9345 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7341
hERG inhibition (predictor II)Inhibitor0.6604
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral20 mg
CapsuleOral5 mg
Solution / dropsOral10 mg
Prices
Unit descriptionCostUnit
Neuleptil 20 mg Capsule0.52USD capsule
Neuleptil 10 mg/ml Drops0.41USD ml
Neuleptil 10 mg Capsule0.34USD capsule
Neuleptil 5 mg Capsule0.21USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point116-117 °CPhysProp
water solubility38 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.52HANSCH,C ET AL. (1995)
logS-3.98ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.059 mg/mLALOGPS
logP3.78ALOGPS
logP3.11ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.18ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.5 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.4 m3·mol-1ChemAxon
Polarizability40.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Benzonitrile
  • Benzenoid
  • Piperidine
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Azacycle
  • Thioether
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
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
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:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Tsukamoto T, Asakura M, Hirata N, Imafuku J, Matsui H, Hasegawa K: Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91. [PubMed:6149771 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on August 29, 2007 12:52 / Updated on August 17, 2016 12:23