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Identification
NamePerphenazine
Accession NumberDB00850  (APRD00429)
TypeSmall Molecule
GroupsApproved
Description

An antipsychotic phenothiazine derivative with actions and uses similar to those of chlorpromazine. [PubChem]

Structure
Thumb
Synonyms
2-(4-[3-(2-chloro-10H-Phenothiazin-10-yl)propyl]-1-piperazinyl)ethanol
2-chloro-10-(3-(4-(2-Hydroxyethyl)piperazin-1-yl)propyl)phenothiazine
4-[3-(2-chloro-10H-Phenothiazin-10-yl)propyl]-1-piperazineethanol
4-[3-(2-Chlorophenothiazin-10-yl)propyl]-1-piperazineethanol
Chlorpiprazine
Etaperazin
Etaperazine
Ethaperazine
gamma-(4-(beta-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine
Perfenazina
Perfenazine
Perphenazin
Perphénazine
Perphenazinum
Trilafon
External Identifiers
  • SC 7105
  • Sch 3940
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Perphenazinetablet16 mgoralAa Pharma Inc1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazinetablet2 mgoralAa Pharma Inc1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazinetablet4 mgoralAa Pharma Inc1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazinetablet8 mgoralAa Pharma Inc1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine 16 Tabtablet16 mgoralPro Doc Limitee1982-12-312010-07-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine 2 Tab 2mgtablet2 mgoralPro Doc Limitee1982-12-312010-07-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine 8 Tab 8mgtablet8 mgoralPro Doc Limitee1982-12-312010-07-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine Tab 2mgtablet2 mgoralD.C. Labs Limited1979-12-312003-07-11Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine Tab 4mgtablet4 mgoralPro Doc Limitee1982-12-312010-07-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Perphenazine Tab 4mgtablet4 mgoralD.C. Labs Limited1979-12-312003-07-11Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Phenazine 16 Tabtablet16 mgoralIcn Canada Ltd.1974-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Phenazine 2 Tabtablet2 mgoralIcn Canada Ltd.1973-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Phenazine 4 Tabtablet4 mgoralIcn Canada Ltd.1973-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Phenazine 8 Tabtablet8 mgoralIcn Canada Ltd.1974-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS Perphenazine Concentrate Liq 3.2mg/mlliquid3.2 mgoralPharmascience Inc1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS Perphenazine Tab 16mgtablet16 mgoralPharmascience Inc1987-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS Perphenazine Tab 2mgtablet2 mgoralPharmascience Inc1987-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS Perphenazine Tab 4mgtablet4 mgoralPharmascience Inc1987-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS Perphenazine Tab 8mgtablet8 mgoralPharmascience Inc1987-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Conc 16mg/5mlliquid16 mgoralSchering Plough Canada Inc1958-12-311997-12-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Inj 5mg/mlsolution5 mgintramuscular; intravenousSchering Plough Canada Inc1958-12-312006-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Syr 2mg/5mlsyrup2 mgoralSchering Plough Canada Inc1958-12-311996-11-08Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Tab 2mgtablet2 mgoralSchering Plough Canada Inc1957-12-312000-07-11Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Tab 4mgtablet4 mgoralSchering Plough Canada Inc1957-12-311998-11-17Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Trilafon Tab 8mgtablet8 mgoralSchering Plough Canada Inc1957-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Perphenazinetablet, film coated2 mg/1oralQualitest Pharmaceuticals1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralREMEDYREPACK INC.2015-09-17Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralREMEDYREPACK INC.2012-09-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralAmerican Health Packaging2014-09-172016-03-31Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, sugar coated8 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralSandoz Inc1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralClinical Solutions Wholesale1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralREMEDYREPACK INC.2013-03-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralAmerican Health Packaging2012-05-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralClinical Solutions Wholesale1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet8 mg/1oralREMEDYREPACK INC.2011-10-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralAmerican Health Packaging2012-04-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralCardinal Health1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralRebel Distributors Corp2010-04-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralContract Pharmacy Services Pa2010-04-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralRebel Distributors Corp2010-04-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralState of Florida DOH Central Pharmacy2014-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralQualitest Pharmaceuticals1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralContract Pharmacy Services Pa2010-04-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, sugar coated2 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralSandoz Inc1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralQualitest Pharmaceuticals1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralREMEDYREPACK INC.2015-10-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, sugar coated8 mg/1oralH.J. Harkins Company, Inc.1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralSandoz Inc1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralClinical Solutions Wholesale1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralREMEDYREPACK INC.2013-03-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralQualitest Pharmaceuticals1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated2 mg/1oralREMEDYREPACK INC.2015-10-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralREMEDYREPACK INC.2013-11-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralAmerican Health Packaging2014-10-092016-04-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated16 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated4 mg/1oralSandoz Inc1988-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralClinical Solutions Wholesale1998-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Perphenazinetablet, film coated8 mg/1oralREMEDYREPACK INC.2013-03-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
DecentanMerck
EmesinalNot Available
FentazinMercury
PerphenanTaro
PZCTanabe Mitsubishi Pharma
TrilafonSchering-Plough
TrilifanNot Available
Brand mixtures
NameLabellerIngredients
Apo Peram Tab 2-25Apotex Inc
Apo Peram Tab 3-15Apotex Inc
Elavil Plus TabTriton Pharma Inc
Etrafon 2 10Schering Plough Canada Inc
Etrafon A TabSchering Plough Canada Inc
Etrafon D TabSchering Plough Canada Inc
Etrafon F TabSchering Plough Canada Inc
Perphenazine and Amitriptyline HydrochlorideMylan Pharmaceuticals Inc.
PMS-levazine 2/25 TabPharmascience Inc
PMS-levazine 3/15 TabPharmascience Inc
PMS-levazine 4/25 TabPharmascience Inc
Proavil TabPro Doc Limitee
Triavil TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
Salts
Name/CASStructureProperties
Perphenazine enanthate
ThumbNot applicableDBSALT000936
Perphenazine heptanoate
ThumbNot applicableDBSALT000937
Categories
UNIIFTA7XXY4EZ
CAS number58-39-9
WeightAverage: 403.969
Monoisotopic: 403.148510866
Chemical FormulaC21H26ClN3OS
InChI KeyInChIKey=RGCVKNLCSQQDEP-UHFFFAOYSA-N
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
IUPAC Name
2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol
SMILES
OCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)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
  • N-alkylpiperazine
  • Chlorobenzene
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl chloride
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Azacycle
  • Thioether
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the management of the manifestations of psychotic disorders and for the control of severe nausea and vomiting in adults.
PharmacodynamicsPerphenazine 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.
Mechanism of actionBinds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone and vomiting centre. Perphenazine also binds the alpha andrenergic receptor. This receptor's action is mediated by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
AbsorptionAbsolute bioavailability is 40% following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationPerphenazine is extensively metabolized in the liver to a number of metabolites by sulfoxidation, hydroxylation, dealkylation, and glucuronidation.
Half life8-12 hours, but ranges up to 20 hours.
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9476
Blood Brain Barrier+0.9683
Caco-2 permeable-0.5126
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.7689
Renal organic cation transporterInhibitor0.5807
CYP450 2C9 substrateNon-substrate0.7442
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.6813
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.9278
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9089
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7548
Ames testNon AMES toxic0.8093
CarcinogenicityNon-carcinogens0.8836
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0725 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7745
hERG inhibition (predictor II)Inhibitor0.7066
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmaceutical assoc inc
  • Schering corp sub schering plough corp
  • Ivax pharmaceuticals inc
  • Sandoz inc
  • Vintage pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral16 mg
Tabletoral2 mg
Tabletoral4 mg
Tabletoral8 mg
Tabletoral8 mg/1
Tablet, film coatedoral16 mg/1
Tablet, film coatedoral2 mg/1
Tablet, film coatedoral4 mg/1
Tablet, film coatedoral8 mg/1
Tablet, sugar coatedoral2 mg/1
Tablet, sugar coatedoral8 mg/1
Tabletoral
Tablet, film coatedoral
Liquidoral3.2 mg
Liquidoral16 mg
Solutionintramuscular; intravenous5 mg
Syruporal2 mg
Prices
Unit descriptionCostUnit
Perphenazine 16 mg tablet1.73USD tablet
Perphenazine 8 mg tablet1.28USD tablet
Perphenazine 4 mg tablet1.05USD tablet
Perphenazine 2 mg tablet0.77USD tablet
Apo-Perphenazine 16 mg Tablet0.13USD tablet
Apo-Perphenazine 8 mg Tablet0.09USD tablet
Apo-Perphenazine 4 mg Tablet0.08USD tablet
Apo-Perphenazine 2 mg Tablet0.07USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point97 °CPhysProp
boiling point278-281 °C at 1.00E+00 mm HgPhysProp
water solubility28.3 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.20HANSCH,C ET AL. (1995)
logS-4.16ADME Research, USCD
pKa7.94SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0237 mg/mLALOGPS
logP4.15ALOGPS
logP3.69ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.95 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.1 m3·mol-1ChemAxon
Polarizability44.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.95 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-gmz4500000-97d36958b3e0fe519db6View in MoNA
References
Synthesis Reference

DrugSyn.org

US2860138
General ReferencesNot Available
External Links
ATC CodesN05AB03
AHFS Codes
  • 28:16.08.24
PDB EntriesNot Available
FDA labelDownload (360 KB)
MSDSDownload (74.9 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Perphenazine can be increased when it is combined with Abiraterone.
AclidiniumAclidinium may increase the anticholinergic activities of Perphenazine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Perphenazine.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Perphenazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmisulprideThe risk or severity of adverse effects can be increased when Perphenazine is combined with Amisulpride.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Perphenazine.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Perphenazine.
AmphetaminePerphenazine may decrease the stimulatory activities of Amphetamine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Perphenazine.
AzelastinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Perphenazine.
BenzphetaminePerphenazine may decrease the stimulatory activities of Benzphetamine.
Botulinum Toxin Type APerphenazine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BPerphenazine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
BromocriptineThe therapeutic efficacy of Perphenazine can be decreased when used in combination with Bromocriptine.
BuprenorphinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Perphenazine.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Perphenazine.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Perphenazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
CathinonePerphenazine may decrease the stimulatory activities of Cathinone.
Cimetropium BromidePerphenazine may increase the anticholinergic activities of Cimetropium Bromide.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Perphenazine.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Perphenazine.
CobicistatThe serum concentration of Perphenazine can be increased when it is combined with Cobicistat.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Perphenazine.
DarunavirThe serum concentration of Perphenazine can be increased when it is combined with Darunavir.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Perphenazine.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Perphenazine.
DextroamphetaminePerphenazine may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Perphenazine.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Perphenazine.
DonepezilDonepezil may increase the central neurotoxic activities of Perphenazine.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Perphenazine.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Perphenazine.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Perphenazine.
EluxadolinePerphenazine may increase the activities of Eluxadoline.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Perphenazine.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Perphenazine.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Perphenazine.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Perphenazine.
EthanolPerphenazine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Perphenazine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Perphenazine.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Perphenazine.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Perphenazine.
GalantamineGalantamine may increase the central neurotoxic activities of Perphenazine.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Perphenazine is combined with Glucagon recombinant.
HydrocodonePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Perphenazine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Perphenazine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Perphenazine.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Perphenazine.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Perphenazine.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Perphenazine.
LisdexamfetaminePerphenazine may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Perphenazine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Perphenazine.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Perphenazine.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Perphenazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Perphenazine.
MequitazinePerphenazine may increase the arrhythmogenic activities of Mequitazine.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Perphenazine.
MethamphetaminePerphenazine may decrease the stimulatory activities of Methamphetamine.
MethotrimeprazinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MethylphenidateThe risk or severity of adverse effects can be increased when Perphenazine is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Perphenazine.
MetyrosinePerphenazine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Perphenazine.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Perphenazine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
MirabegronThe risk or severity of adverse effects can be increased when Perphenazine is combined with Mirabegron.
MirtazapinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Perphenazine.
MorphinePerphenazine may increase the hypotensive activities of Morphine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Perphenazine.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Perphenazine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Perphenazine.
OrphenadrinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PanobinostatThe serum concentration of Perphenazine can be increased when it is combined with Panobinostat.
ParaldehydePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Paroxetine.
Peginterferon alfa-2bThe serum concentration of Perphenazine can be decreased when it is combined with Peginterferon alfa-2b.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Perphenazine.
PhendimetrazinePerphenazine may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Perphenazine.
PhenterminePerphenazine may decrease the stimulatory activities of Phentermine.
PorfimerPerphenazine may increase the photosensitizing activities of Porfimer.
Potassium ChloridePerphenazine may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Perphenazine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Perphenazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Perphenazine.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Perphenazine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Perphenazine.
PyrimethamineThe serum concentration of Perphenazine can be increased when it is combined with Pyrimethamine.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Perphenazine.
RamosetronPerphenazine may increase the activities of Ramosetron.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Perphenazine.
RitonavirThe metabolism of Perphenazine can be decreased when combined with Ritonavir.
RivastigmineRivastigmine may increase the central neurotoxic activities of Perphenazine.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Perphenazine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Perphenazine.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Perphenazine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Perphenazine.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Perphenazine.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
SulpirideThe risk or severity of adverse effects can be increased when Perphenazine is combined with Sulpiride.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Perphenazine.
SuvorexantPerphenazine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Perphenazine can be decreased when used in combination with Tacrine.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Perphenazine.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Perphenazine.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Perphenazine.
ThalidomidePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThiopentalThe risk or severity of adverse effects can be increased when Perphenazine is combined with Thiopental.
TiclopidineThe metabolism of Perphenazine can be decreased when combined with Ticlopidine.
TiotropiumPerphenazine may increase the anticholinergic activities of Tiotropium.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Perphenazine.
TopiramateThe risk or severity of adverse effects can be increased when Perphenazine is combined with Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Perphenazine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Perphenazine.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Perphenazine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Perphenazine.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Perphenazine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Perphenazine.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Perphenazine.
VerteporfinPerphenazine may increase the photosensitizing activities of Verteporfin.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Perphenazine.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Perphenazine.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Perphenazine.
ZolpidemPerphenazine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.
  • Take with food.

Targets

1. D(2) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. Pubmed
  2. Hoyberg OJ, Fensbo C, Remvig J, Lingjaerde O, Sloth-Nielsen M, Salvesen I: Risperidone versus perphenazine in the treatment of chronic schizophrenic patients with acute exacerbations. Acta Psychiatr Scand. 1993 Dec;88(6):395-402. Pubmed
  3. Qin ZH, Weiss B: Dopamine receptor blockade increases dopamine D2 receptor and glutamic acid decarboxylase mRNAs in mouse substantia nigra. Eur J Pharmacol. 1994 Sep 15;269(1):25-33. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  5. Talvik M, Nordstrom AL, Larsen NE, Jucaite A, Cervenka S, Halldin C, Farde L: A cross-validation study on the relationship between central D2 receptor occupancy and serum perphenazine concentration. Psychopharmacology (Berl). 2004 Sep;175(2):148-53. Epub 2004 Mar 6. Pubmed
  6. Farde L, Wiesel FA, Nordstrom AL, Sedvall G: D1- and D2-dopamine receptor occupancy during treatment with conventional and atypical neuroleptics. Psychopharmacology (Berl). 1989;99 Suppl:S28-31. Pubmed

2. D(1A) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details

References:

  1. Dolzan V, Plesnicar BK, Serretti A, Mandelli L, Zalar B, Koprivsek J, Breskvar K: Polymorphisms in dopamine receptor DRD1 and DRD2 genes and psychopathological and extrapyramidal symptoms in patients on long-term antipsychotic treatment. Am J Med Genet B Neuropsychiatr Genet. 2007 Sep 5;144(6):809-15. Pubmed
  2. Farde L, Wiesel FA, Nordstrom AL, Sedvall G: D1- and D2-dopamine receptor occupancy during treatment with conventional and atypical neuroleptics. Psychopharmacology (Berl). 1989;99 Suppl:S28-31. Pubmed

3. Calmodulin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Calmodulin P62158 Details

References:

  1. Mongin AA, Cai Z, Kimelberg HK: Volume-dependent taurine release from cultured astrocytes requires permissive [Ca(2+)](i) and calmodulin. Am J Physiol. 1999 Oct;277(4 Pt 1):C823-32. Pubmed
  2. Kawai M, Nakashima A, Ueno M, Ushimaru T, Aiba K, Doi H, Uritani M: Fission yeast tor1 functions in response to various stresses including nitrogen starvation, high osmolarity, and high temperature. Curr Genet. 2001 May;39(3):166-74. Pubmed
  3. Edlind T, Smith L, Henry K, Katiyar S, Nickels J: Antifungal activity in Saccharomyces cerevisiae is modulated by calcium signalling. Mol Microbiol. 2002 Oct;46(1):257-68. Pubmed
  4. Natochin YuV, Shakhmatova EI, Bakos P: Water and sodium transport: effects of calcium channel blocker and calmodulin antagonists on the apical and basolateral membranes of amphibian epithelia. Gen Physiol Biophys. 1987 Feb;6(1):35-44. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. Pubmed
  2. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
  3. Linnet K, Wiborg O: Steady-state serum concentrations of the neuroleptic perphenazine in relation to CYP2D6 genetic polymorphism. Clin Pharmacol Ther. 1996 Jul;60(1):41-7. Pubmed
  4. Ozdemir V, Naranjo CA, Herrmann N, Reed K, Sellers EM, Kalow W: Paroxetine potentiates the central nervous system side effects of perphenazine: contribution of cytochrome P4502D6 inhibition in vivo. Clin Pharmacol Ther. 1997 Sep;62(3):334-47. Pubmed
  5. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. Pubmed
  6. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  7. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2B6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2C18

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C18 P33260 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2C19

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 22, 2013 22:48