perphenazine ๐Ÿถ Veterinary Use | 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 ยตM/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
S (Water solubility) 0.02 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

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
Blood magnesium increased 79.69 27.36 20 2870 3018 63483114
Pleural fibrosis 77.04 27.36 20 2870 3452 63482680
Presbyacusis 75.84 27.36 19 2871 2846 63483286
Pleural thickening 75.72 27.36 19 2871 2864 63483268
Tardive dyskinesia 71.43 27.36 23 2867 8479 63477653
Deafness neurosensory 65.91 27.36 19 2871 4836 63481296
Sopor 62.88 27.36 27 2863 22137 63463995
Drug abuse 60.83 27.36 39 2851 72479 63413653
Neuroleptic malignant syndrome 59.83 27.36 22 2868 12034 63474098
Epigastric discomfort 59.65 27.36 19 2871 6761 63479371
Mitochondrial encephalomyopathy 53.04 27.36 7 2883 22 63486110
Cyst 49.49 27.36 20 2870 14079 63472053
Ileus paralytic 45.23 27.36 14 2876 4537 63481595
Blood potassium increased 44.46 27.36 20 2870 18289 63467843
Osteopenia 42.97 27.36 20 2870 19765 63466367
Extrapyramidal disorder 40.37 27.36 17 2873 13267 63472865
Bone cyst 35.91 27.36 10 2880 2244 63483888
Deformity 35.66 27.36 15 2875 11669 63474463
Moaning 34.74 27.36 8 2882 838 63485294
Skin lesion 34.67 27.36 20 2870 30701 63455431
Osteosclerosis 34.62 27.36 11 2879 3877 63482255
Hyperprolactinaemia 34.59 27.36 11 2879 3889 63482243
Intentional self-injury 32.43 27.36 18 2872 25669 63460463
Onychophagia 31.32 27.36 5 2885 72 63486060
Multiple drug therapy 31.17 27.36 10 2880 3636 63482496
Metabolic syndrome 29.74 27.36 8 2882 1580 63484552
Dry eye 29.47 27.36 20 2870 40741 63445391
Muscle rigidity 29.31 27.36 13 2877 11487 63474645
Toxicity to various agents 28.82 27.36 45 2845 247205 63238927
Bradykinesia 27.71 27.36 10 2880 5178 63480954
Overdose 27.70 27.36 30 2860 115048 63371084
Sports injury 27.43 27.36 4 2886 30 63486102

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 464.17 46.23 111 2648 7998 34946174
Antipsychotic drug level below therapeutic 461.05 46.23 90 2669 2457 34951715
Therapeutic product effect variable 445.85 46.23 87 2672 2369 34951803
Disinhibition 439.83 46.23 90 2669 3136 34951036
Obsessive-compulsive disorder 434.16 46.23 98 2661 5466 34948706
Euphoric mood 400.43 46.23 92 2667 5549 34948623
Increased appetite 365.08 46.23 90 2669 7339 34946833
Suicide attempt 238.63 46.23 96 2663 39020 34915152
Therapeutic product effect incomplete 189.54 46.23 88 2671 50453 34903719
Leukaemia 177.44 46.23 46 2713 4557 34949615
Leukopenia 168.39 46.23 87 2672 62769 34891403
Dyslipidaemia 164.06 46.23 48 2711 7440 34946732
Weight increased 162.18 46.23 97 2662 92936 34861236
Toxicity to various agents 159.94 46.23 129 2630 200233 34753939
Obesity 134.59 46.23 47 2712 12831 34941341
Prescribed overdose 123.44 46.23 42 2717 10605 34943567
Drug ineffective 73.12 46.23 129 2630 456622 34497550
Schizoaffective disorder 69.68 46.23 17 2742 1310 34952862
Neuroleptic malignant syndrome 69.37 46.23 32 2727 17902 34936270
Irritability 54.11 46.23 30 2729 24660 34929512

FDA Adverse Event Reporting System (Geriatric)

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 163.14 27.36 50 4271 13209 79726858
Antipsychotic drug level below therapeutic 123.16 27.36 25 4296 1213 79738854
Therapeutic product effect variable 116.56 27.36 26 4295 1983 79738084
Neuroleptic malignant syndrome 106.56 27.36 44 4277 27515 79712552
Disinhibition 104.70 27.36 25 4296 2573 79737494
Obsessive-compulsive disorder 93.06 27.36 27 4294 5900 79734167
Euphoric mood 86.00 27.36 27 4294 7699 79732368
Toxicity to various agents 75.73 27.36 103 4218 421437 79318630
Dyslipidaemia 75.16 27.36 27 4294 11606 79728461
Presbyacusis 73.93 27.36 19 4302 2641 79737426
Blood magnesium increased 73.37 27.36 20 4301 3486 79736581
Pleural thickening 71.78 27.36 19 4302 2963 79737104
Increased appetite 67.00 27.36 25 4296 11953 79728114
Tardive dyskinesia 66.28 27.36 24 4297 10547 79729520
Pleural fibrosis 65.49 27.36 19 4302 4148 79735919
Completed suicide 59.85 27.36 70 4251 245697 79494370
Deafness neurosensory 56.06 27.36 19 4302 6879 79733188
Hyperprolactinaemia 54.79 27.36 17 4304 4659 79735408
Epigastric discomfort 53.54 27.36 19 4302 7877 79732190
Ileus paralytic 53.51 27.36 20 4301 9600 79730467
Enuresis 52.21 27.36 15 4306 3161 79736906
Obesity 51.98 27.36 29 4292 35096 79704971
Sopor 50.89 27.36 28 4293 32982 79707085
Mitochondrial encephalomyopathy 50.11 27.36 7 4314 30 79740037
Schizoaffective disorder 48.42 27.36 13 4308 2139 79737928
Cyst 46.46 27.36 20 4301 13820 79726247
Intentional self-injury 45.89 27.36 26 4295 32393 79707674
Suicide attempt 45.62 27.36 37 4284 82895 79657172
Irritability 42.64 27.36 27 4294 41117 79698950
Osteopenia 38.07 27.36 19 4302 18345 79721722
Drug abuse 37.32 27.36 45 4276 162646 79577421
Muscle rigidity 36.64 27.36 19 4302 19863 79720204
Prescribed overdose 34.68 27.36 23 4298 37860 79702207
Extrapyramidal disorder 34.29 27.36 19 4302 22660 79717407
Deformity 32.63 27.36 14 4307 9591 79730476
Sedation 32.49 27.36 25 4296 51870 79688197
Blood potassium increased 32.31 27.36 20 4301 29255 79710812
Bradyphrenia 31.25 27.36 14 4307 10626 79729441
Moaning 31 27.36 8 4313 1129 79738938
Weight increased 30.27 27.36 54 4267 277332 79462735
Bone cyst 30.04 27.36 10 4311 3423 79736644
Onychophagia 28.67 27.36 5 4316 105 79739962
Osteosclerosis 28.62 27.36 10 4311 3961 79736106
Multiple drug therapy 28.36 27.36 10 4311 4068 79735999
Dry eye 28.08 27.36 20 4301 36911 79703156

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AB03 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA CS M0016525 Phenothiazines
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 antipsychotic drugs
CHEBI has role CHEBI:48561 dopaminergic antagonists
CHEBI has role CHEBI:50919 antiemetico
FDA EPC N0000175746 Phenothiazine

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
5-hydroxytryptamine receptor 1A GPCR Ki 6.07 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.25 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.19 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.46 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 7.55 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 7.64 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 6.98 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 9.52 WOMBAT-PK
Histamine H1 receptor GPCR Ki 8.09 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 5.73 PDSP
Aldehyde oxidase Enzyme IC50 7.48 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.07 WOMBAT-PK
D(4) dopamine receptor GPCR Ki 7.59 WOMBAT-PK
Retinal dehydrogenase 1 Enzyme IC50 6.28 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 6.88 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.60 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.80 IUPHAR
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.85 CHEMBL

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
4748 PUBCHEM_CID
209 IUPHAR_LIGAND_ID
637 INN_ID
FTA7XXY4EZ UNII
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 0378-0042 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 0378-0073 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 0378-0330 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 0378-0442 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 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 0603-5060 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 0603-5061 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 0603-5062 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 0603-5063 TABLET, FILM COATED 16 mg ORAL ANDA 19 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8046 TABLET, FILM COATED 2 mg ORAL ANDA 20 sections
Perphenazine HUMAN PRESCRIPTION DRUG LABEL 1 0781-8046 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 0781-8047 TABLET, FILM COATED 4 mg ORAL ANDA 20 sections