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Details

Stereochemistry ACHIRAL
Molecular Formula C21H26ClN3OS
Molecular Weight 403.969
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERPHENAZINE

SMILES

OCCN1CCN(CCCN2C3=CC=CC=C3SC4=CC=C(Cl)C=C24)CC1

InChI

InChIKey=RGCVKNLCSQQDEP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Perphenazine is a relatively high potency phenothiazine that blocks dopamine 2 receptors predominantly, but also may possess antagonist actions at histamine 1 and cholinergic M1 and alpha 1 adrenergic receptors in the vomiting center leading to reduced nausea and vomiting. The drug was approved by FDA for the treatment of schizophrenia and control of severe nausea and vomiting (either alone or in combination with amitriptyline hydrochloride). Perphenazine is extensively hepatic to metabolites via sulfoxidation, hydroxylation, dealkylation, and glucuronidation; primarily metabolized by CYP2D6 to N-dealkylated perphenazine, perphenazine sulfoxide, and 7-hydroxyperphenazine (active metabolite with 70% of the activity of perphenazine) and excreted in the urine and feces.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967 Jan
Metoclopramide and dystonic reactions in Sardinians.
1979 Jun 23
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.
2003 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

In Vivo Use Guide
Moderately disturbed nonhospitalized patients with schizophrenia: 4 to 8 mg t.i.d. initially; reduce as soon as possible to minimum effective dosage. Hospitalized patients with schizophrenia: 8 to 16 mg b.i.d. to q.i.d.; avoid dosages in excess of 64 mg daily. Severe nausea and vomiting in adults: 8 to 16 mg daily in divided doses; 24 mg occasionally may be necessary; early dosage reduction is desirable.
Route of Administration: Oral
In Vitro Use Guide
Perphenazine (10-100 microM) was administered, either alone or combined with dopamine, to primary mouse neuronal or intact brain culture and to a human neuroblastoma (NB) cell line (SK-N-SH). Cell viability (measured by neutral red and alamar blue), DNA fragmentation (flow cytometry-NB) were determined. Neuroblastoma: perphenazine decreased viability by 87%.
Name Type Language
PERPHENAZINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
PERPHENAZINE [EP]
Common Name English
PERPHENAZINE COMPONENT OF ETRAFON-A
Common Name English
PIPERAZINEETHANOL, 4-(3-(2-CHLORO-10H-PHENOTHIAZIN-10-YL)PROPYL)-
Systematic Name English
PERPHENAZINE [HSDB]
Common Name English
4-(3-(2-CHLOROPHENOTHIAZIN-10-YL)PROPYL)-1-PIPERAZINEETHANOL
Systematic Name English
TRILAFON
Brand Name English
PERPHENAZINE [VANDF]
Common Name English
PERPHENAZINE [MART.]
Common Name English
PERPHENAZINE [USP]
Common Name English
PERPHENAZINE MALEATE [JAN]
Common Name English
PERPHENAZINE [JAN]
Common Name English
PERPHENAZINE [WHO-DD]
Common Name English
NSC-150866
Code English
ETRAFON-A COMPONENT PERPHENAZINE
Common Name English
PERPHENAZINE [INN]
Common Name English
FLUPHENAZINE DIHYDROCHLORIDE IMPURITY E [EP]
Common Name English
PERPHENAZINE [USP-RS]
Common Name English
PERPHENAZINE [ORANGE BOOK]
Common Name English
PERPHENAZINE [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175746
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
WHO-VATC QN05AB03
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
LIVERTOX 764
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
NDF-RT N0000007544
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
NDF-RT N0000007544
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
NDF-RT N0000007544
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
WHO-ATC N05AB03
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
Code System Code Type Description
RXCUI
8076
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY RxNorm
INN
637
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
EVMPD
SUB09736MIG
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
ChEMBL
CHEMBL567
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
EPA CompTox
58-39-9
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
DRUG BANK
DB00850
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
MESH
D010546
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
WIKIPEDIA
PERPHENAZINE
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
NCI_THESAURUS
C29355
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
PUBCHEM
4748
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY SWITZERF
CAS
58-39-9
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-381-5
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
MERCK INDEX
M8567
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY Merck Index
LactMed
58-39-9
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
HSDB
58-39-9
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY
IUPHAR
209
Created by admin on Tue Mar 06 10:25:18 UTC 2018 , Edited by admin on Tue Mar 06 10:25:18 UTC 2018
PRIMARY