2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

• ChemBase ID: 728
• Molecular Formular: C21H26ClN3OS
• Molecular Mass: 403.96864
• Monoisotopic Mass: 403.14851115
• SMILES: Clc1cc2N(CCCN3CCN(CC3)CCO)c3c(Sc2cc1)cccc3
• Canonical SMILES: OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
• InChIKey: RGCVKNLCSQQDEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol
• IUPAC Traditional name: perphenazine
• Brand Name: Apo-Perphenazine; Decentan; Emesinal; Etrafon-A; Etrafon-Forte; F-Mon; Fentazin; Perphenan; Thilatazin; Trifaron; Trilafon; Trilifan; Triphenot
• Synonyms: 4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-(piperazine-d8)ethanol Dihydrochloride; 1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine-d8-Dihydrochloride; Chloriprozine-d8; Chlorperphenazine-d8; Decentan-d8; Emesinal-d8; Etaperazin-d8; Perfenil-d8; Perphenan-d8; Perphenazin-d8; Sch 3940-d8; Thilatazin-d8; Perphenazine-d8 Dihydrochloride; 2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol; PZC; Perphenazin; Perfenazine; Perfenazina; Chlorperphenazine; Etaperazin; Etaperazine; Ethaperazine; Perphenazine; Perphenazine

Database IDs

• CAS Number: 58-39-9
• EC Number: 200-381-5
• MDL Number: MFCD00056798
• PubChem SID: 160964191; 24278642; 46507058
• PubChem CID: 4748
• CHEBI ID: 8028
• ATC CODE: N05AB03
• CHEMBL: 567
• Chemspider ID: 4586
• DrugBank ID: DB00850
• IUPHAR ligand ID: 209
• KEGG ID: D00503
• Unique Ingredient Identifier: FTA7XXY4EZ
• Wikipedia Title: Perphenazine
• Medline Plus: a682165

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.593098
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0448196
• LogD (pH = 7.4): 2.8195775
• Log P: 3.6920178
• Molar Refractivity: 116.0987 cm^3
• Polarizability: 44.746113 Å^3
• Polar Surface Area: 29.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.15
• LOG S: -4.23
• Solubility (Water): 2.37e-02 g/l

PROPERTIES

Physical Property

• Solubility: 28.3 mg/L; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 190-193°C
• Hydrophobicity(logP): 3.807; 3.9

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 28-36/37/39-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: oral and i.m.
• Bioavailability: 40%
• Half Life: 8-12 (up to 20) hours
• Metabolism: hepatic
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C (Australia); C (US)
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152), DRD2(1813), OPRS1(10280)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00850

• Drug Groups: approved
• Description: An antipsychotic phenothiazine derivative with actions and uses similar to those of chlorpromazine. [PubChem]
• Indication: For use in the management of the manifestations of psychotic disorders and for the control of severe nausea and vomiting in adults.
• Pharmacology: Perphenazine is a piperazinyl phenothiazine, acts on the central nervous system, and has a greater behavioral potency than other phenothiazine derivatives whose side chains do not contain a piperazine moiety. It is a member of a class of drugs called phenothiazines, which are dopamine D1/D2 receptor antagonists. Perphenazine is 10 to 15 times as potent as chlorpromazine; that means perphenazine is a highly potent antipsychotic. In equivalent doses it has approximately the same frequency and severity of early and late extrapypramidal side-effects compared to Haloperidol.
• Toxicity: Symptoms of overdose include stupor or coma, and children may have convulsive seizures. Signs of arousal may not occur for 48 hours. Oral LD₅₀=318 mg/kg (rat); IPR LD₅₀=64 mg/kg (mouse)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Absolute bioavailability is 40% following oral administration.
• Half Life: 8-12 hours, but ranges up to 20 hours.
• Elimination: Perphenazine is extensively metabolized in the liver to a number of metabolites by sulfoxidation, hydroxylation, dealkylation, and glucuronidation.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P6402

Biochem/physiol Actions
D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P6402.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P291102

Labelled Perphenazine. D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.

REFERENCES

• Gaertner, H.J., et al.: Drug Metab. Dispos., 3, 437 (1975)
• O Brien, S., et al.: J. Med. Chem., 48, 1287 (1975)
• Briggs, K., et al.: Toxicology, 231, 113 (1975)
• Toga, T., et al.: J. Pharmacol. Sci., 105, 207 (1975)