perphenazine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2113 58-39-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • perphenazine
  • perfenazine
  • perfenil
  • perphenan
  • perphenazin
  • thilatazin
  • tranquisan
  • perphanzine
An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.
  • Molecular weight: 403.97
  • Formula: C21H26ClN3OS
  • CLOGP: 4.01
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 29.95
  • ALOGS: -4.23
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
30 mg O
7 mg P
10 mg P
16 mg R

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.99 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 18 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 27 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.07 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 9.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 27, 1957 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Sopor 80.60 24.68 34 2834 19794 46663400
Blood magnesium increased 69.16 24.68 19 2849 3008 46680186
Pleural thickening 67.29 24.68 18 2850 2577 46680617
Pleural fibrosis 66.06 24.68 19 2849 3550 46679644
Presbyacusis 65.80 24.68 18 2850 2804 46680390
Deafness neurosensory 57.53 24.68 18 2850 4476 46678718
Drug abuse 57.29 24.68 40 2828 63368 46619826
Epigastric discomfort 53.37 24.68 18 2850 5666 46677528
Cyst 43.38 24.68 19 2849 12081 46671113
Ileus paralytic 41.81 24.68 14 2854 4309 46678885
Osteopenia 37.26 24.68 19 2849 16942 46666252
Blood potassium increased 37.26 24.68 19 2849 16948 46666246
Mitochondrial encephalomyopathy 36.56 24.68 5 2863 15 46683179
Deformity 34.74 24.68 14 2854 7243 46675951
Moaning 33.36 24.68 8 2860 738 46682456
Wrist deformity 32.20 24.68 9 2859 1515 46681679
Bradykinesia 31.17 24.68 11 2857 3955 46679239
Tardive dyskinesia 30.84 24.68 13 2855 7530 46675664
Bone cyst 29.56 24.68 9 2859 2042 46681152
Drug interaction 29.37 24.68 48 2820 203046 46480148
Skin lesion 29.23 24.68 19 2849 26694 46656500
Metabolic syndrome 29.04 24.68 8 2860 1276 46681918
Neuroleptic malignant syndrome 28.99 24.68 14 2854 11108 46672086
Osteosclerosis 28.58 24.68 10 2858 3506 46679688
Intentional self-injury 28.45 24.68 18 2850 24148 46659046
Muscle rigidity 27.37 24.68 13 2855 9948 46673246
Dry eye 27.04 24.68 19 2849 30303 46652891
Hyperprolactinaemia 26.40 24.68 9 2859 2923 46680271
Sports injury 26.24 24.68 4 2864 30 46683164
Blood glucose 26.12 24.68 4 2864 31 46683163

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Akathisia 183.26 46.34 46 1586 5858 29944988
Obsessive-compulsive disorder 178.28 46.34 42 1590 4099 29946747
Antipsychotic drug level below therapeutic 174.51 46.34 34 1598 1338 29949508
Therapeutic product effect variable 174.09 46.34 34 1598 1355 29949491
Disinhibition 162.46 46.34 34 1598 1923 29948923
Euphoric mood 145.96 46.34 36 1596 4254 29946592
Increased appetite 126.81 46.34 34 1598 5583 29945263
Toxicity to various agents 85.59 46.34 73 1559 177110 29773736
Dyslipidaemia 80.71 46.34 24 1608 5703 29945143
Suicide attempt 73.35 46.34 37 1595 36660 29914186
Therapeutic product effect incomplete 70.21 46.34 35 1597 33799 29917047
Obesity 67.29 46.34 23 1609 8532 29942314
Leukopenia 66.30 46.34 40 1592 56119 29894727
Weight increased 53.48 46.34 39 1593 74874 29875972
Neuroleptic malignant syndrome 52.89 46.34 23 1609 16272 29934574

Pharmacologic Action:

SourceCodeDescription
ATC N05AB03 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA CS M0016525 Phenothiazines
FDA EPC N0000175746 Phenothiazine
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:37930 phenothiazine antipsychotics
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:50919 antiemetico

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nausea and vomiting indication 16932000
Schizophrenia indication 58214004 DOID:5419
Mixed anxiety and depressive disorder indication 231504006
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
Sinus tachycardia contraindication 11092001
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Chronic disease of respiratory system contraindication 17097001
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Paralytic ileus contraindication 55525008 DOID:8442
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
Chronic idiopathic constipation contraindication 82934008
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Acute disease of cardiovascular system contraindication 128487001
Bipolar affective disorder, current episode manic contraindication 191618007
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Metabolic syndrome X contraindication 237602007 DOID:14221
Hyperprolactinemia contraindication 237662005 DOID:12700
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Syncope contraindication 271594007
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
At risk for aspiration contraindication 371736008
Angle-closure glaucoma contraindication 392291006 DOID:13550
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.21 Basic
pKa2 4.21 Basic
pKa3 2.21 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(2) dopamine receptor GPCR ANTAGONIST Ki 9.32 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.46 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 7.59 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.07 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 7.48 WOMBAT-PK
Histamine H1 receptor GPCR Ki 8.09 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 9.52 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 6.98 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 7.64 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.55 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.88 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.25 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.07 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.19 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 5.73 PDSP
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.85 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.80 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.60 IUPHAR

External reference:

IDSource
4017939 VUID
N0000146289 NUI
D00503 KEGG_DRUG
4017939 VANDF
C0031184 UMLSCUI
CHEBI:8028 CHEBI
CHEMBL567 ChEMBL_ID
D010546 MESH_DESCRIPTOR_UI
DB00850 DRUGBANK_ID
209 IUPHAR_LIGAND_ID
637 INN_ID
FTA7XXY4EZ UNII
4748 PUBCHEM_CID
8076 RXNORM
2271 MMSL
5261 MMSL
d00855 MMSL
001477 NDDF
387229007 SNOMEDCT_US
41147003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0042 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0073 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0330 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0442 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0574 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0378-5350 TABLET, FILM COATED 2 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0378-5351 TABLET, FILM COATED 4 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0378-5352 TABLET, FILM COATED 8 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0378-5353 TABLET, FILM COATED 16 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4101 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4102 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4103 TABLET, FILM COATED 8 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4104 TABLET, FILM COATED 16 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0603-5060 TABLET, FILM COATED 2 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0603-5061 TABLET, FILM COATED 4 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0603-5062 TABLET, FILM COATED 8 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0603-5063 TABLET, FILM COATED 16 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-3584 TABLET, FILM COATED 2 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-3585 TABLET, FILM COATED 4 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0615-4511 TABLET, FILM COATED 8 mg ORAL ANDA 18 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-1046 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-1047 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-1048 TABLET, FILM COATED 8 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-1049 TABLET, FILM COATED 16 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8046 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8047 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8048 TABLET, FILM COATED 8 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8049 TABLET, FILM COATED 16 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6599 TABLET, FILM COATED 2 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6600 TABLET, FILM COATED 4 mg ORAL ANDA 19 sections