Identification

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Name
Periciazine
Accession Number
DB01608
Type
Small Molecule
Groups
Approved, Investigational
Description

Periciazine 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
  • Périciazine
  • Periciazine
  • Periciazinum
  • Pericyazine
  • Piperocyanomazine
  • Propericiazine
External IDs
RP 8909 / RP-8909 / SKF 20716 / SKF-20716
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NeuleptilCapsuleOralErfa Canada 2012 Inc1969-12-31Not applicableCanada
NeuleptilCapsuleOralErfa Canada 2012 Inc1969-12-31Not applicableCanada
NeuleptilCapsuleOralErfa Canada 2012 Inc1976-12-31Not applicableCanada
NeuleptilSolution / dropsOralErfa Canada 2012 Inc1976-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Neulactil / Neuleptil
Categories
UNII
3405M6FD73
CAS number
2622-26-6
Weight
Average: 365.492
Monoisotopic: 365.156183063
Chemical Formula
C21H23N3OS
InChI Key
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

Pharmacology

Indication

For use as adjunctive medication in some psychotic patients. Propericiazine (Pericyazine)is used for the control of residual prevailing hostility, impulsiveness and aggressiveness.

Associated Conditions
Pharmacodynamics

Pericyazine 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 action

Pericyazine, 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.

TargetActionsOrganism
ADopamine D1 receptor
antagonist
Humans
AAlpha-2A adrenergic receptor
antagonist
Humans
UAlpha-1B adrenergic receptor
antagonist
Humans
UAndrogen receptorNot AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

In 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Periciazine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Periciazine is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Periciazine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Periciazine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-DinitrocatecholThe therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Periciazine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Periciazine can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Periciazine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Periciazine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Periciazine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Periciazine is combined with 7-Nitroindazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015546
KEGG Drug
D01485
PubChem Compound
4747
PubChem Substance
46505085
ChemSpider
4585
BindingDB
50346422
ChEBI
31981
ChEMBL
CHEMBL251940
Therapeutic Targets Database
DAP000413
PharmGKB
PA164781043
Wikipedia
Propericiazine
ATC Codes
N05AC01 — Periciazine
AHFS Codes
  • 28:16.08.24 — Phenothiazines

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentPsychosis Nos/Other1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral
Solution / dropsOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116-117 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03xu-7932000000-163720fa7ee8e5adf313
GC-MS Spectrum - EI-BGC-MSsplash10-03di-4931000000-bc6eaf361b17af48a30f
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 / Piperidines / Benzenoids / 1,4-thiazines / Trialkylamines / Secondary alcohols / Nitriles / Azacyclic compounds / Organopnictogen compounds
show 1 more
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / Para-thiazine / Piperidine / Benzenoid / Secondary alcohol / Tertiary aliphatic amine
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, nitrile, hydroxypiperidine (CHEBI:31981)

Targets

Kind
Protein
Organism
Humans
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
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
Humans
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
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
Humans
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Bisson WH, Cheltsov AV, Bruey-Sedano N, Lin B, Chen J, Goldberger N, May LT, Christopoulos A, Dalton JT, Sexton PM, Zhang XK, Abagyan R: Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs. Proc Natl Acad Sci U S A. 2007 Jul 17;104(29):11927-32. Epub 2007 Jul 2. [PubMed:17606915]

Drug created on August 29, 2007 12:52 / Updated on January 24, 2020 15:33