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Identification
NamePropericiazine
Accession NumberDB01608
TypeSmall Molecule
GroupsApproved
Description

Propericiazine 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/mldrops10 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 KeyInChIKey=LUALIOATIOESLM-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
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
Pharmacology
IndicationFor use as adjunctive medication in some psychotic patients. Propericiazine (Pericyazine)is used for the control of residual prevailing hostility, impulsiveness and aggressiveness.
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.
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
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
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
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesN05AC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 September 16, 2013 17:15