fluphenazine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
1212 69-23-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fluphenazine
  • fluorfenazine
  • fluorophenazine
  • fluorphenazine
  • ftorphenazine
  • phthorphenazine
  • fluphenazine hydrochloride
  • fluphenazine dihydrochloride
  • fluphenazine HCl
  • flufenazin
A phenothiazine used in the treatment of PSYCHOSES. Its properties and uses are generally similar to those of CHLORPROMAZINE.
  • Molecular weight: 437.53
  • Formula: C22H26F3N3OS
  • CLOGP: 4.32
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 29.95
  • ALOGS: -4.36
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
10 mg O
1 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.03 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.65 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 2.70 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12.30 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.782 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.132 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 28.184 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 38.194 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 1.780 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 4.880 % High 1
herg hERG pIC50 5.994 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 38.019 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 66.222 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 1.630 % High 1
kinase-safety-class ACVR2B,AKT2,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,JAK3,MAP3K7,MAPK10,MAPK7,MET,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKDC,SIK2,TEK,TGFBR1 31
kinase-selectivity-class AXL,EPHB4,PDK4 3
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 3.556 High 1
mh-clint Mouse hepatocyte intrinsic clearance 126.765 High 1
mppb Mouse plasma protein binding (% unbound) 2.280 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 9.638 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 1
pppb Pig plasma protein binding (% unbound) 5.050 % High 1
rh-clint Rat hepatocyte intrinsic clearance 227.510 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 11.250 % High 1
rppb Rat plasma protein binding (% unbound) 1.730 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 33.343 uM High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 9, 1959 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
Neuroleptic malignant syndrome 88.47 37.62 23 1082 15073 90612269
Akathisia 60.53 37.62 16 1089 11143 90616199
Extrapyramidal disorder 54.52 37.62 16 1089 16287 90611055
Salivary hypersecretion 53.94 37.62 14 1091 9078 90618264
Accommodation disorder 50.98 37.62 8 1097 406 90626936
Blood prolactin increased 49.75 37.62 11 1094 3626 90623716
Suicide attempt 45.81 37.62 21 1084 75378 90551964
Intentional overdose 38.53 37.62 20 1085 93814 90533528
Torsade de pointes 38.31 37.62 12 1093 15170 90612172

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
Priapism 146.92 39.54 35 1277 6372 42613651
Neuroleptic malignant syndrome 125.37 39.54 40 1272 21432 42598591
Sedation 123.10 39.54 43 1269 30432 42589591
Compartment syndrome 60.16 39.54 15 1297 3274 42616749
Salivary hypersecretion 58.09 39.54 19 1293 10924 42609099
Torsade de pointes 54.14 39.54 17 1295 8577 42611446
Parkinsonism 46.67 39.54 16 1296 10607 42609416
Completed suicide 42.64 39.54 30 1282 96435 42523588

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
Neuroleptic malignant syndrome 221.25 40.69 63 2239 33996 110553001
Priapism 146.57 40.69 32 2270 5829 110581168
Salivary hypersecretion 120.99 40.69 34 2268 17387 110569610
Torsade de pointes 87.05 40.69 28 2274 22572 110564425
Extrapyramidal disorder 84.20 40.69 29 2273 28838 110558159
Sedation 74.93 40.69 34 2268 69649 110517348
Parkinsonism 67.46 40.69 23 2279 22164 110564833
Akathisia 65.06 40.69 21 2281 17092 110569905
Compartment syndrome 57.22 40.69 15 2287 5895 110581102
Tardive dyskinesia 44.90 40.69 15 2287 13564 110573433
Rhabdomyolysis 44.67 40.69 29 2273 120372 110466625
Accommodation disorder 43.05 40.69 8 2294 645 110586352

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AB02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA CS M0016525 Phenothiazines
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014150 Antipsychotic Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018492 Dopamine Antagonists
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:37930 phenothiazine antipsychotic drug
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:149553 anticoronaviral agent
CHEBI has role CHEBI:35610 antineoplastic agent
FDA EPC N0000175746 Phenothiazine

Related Drugs by ATC class:

N05AB Phenothiazines with piperazine structure 9 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419
Psychotic disorder indication 69322001
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
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
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
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
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
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
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
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 2.72 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 9.27 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 7.60 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.08 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 7.65 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.50 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 8.07 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.33 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.10 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.71 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 6.84 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.04 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 7.46 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 7.46 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 8.10 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.19 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7.09 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 9.37 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 7.89 WOMBAT-PK
Histamine H1 receptor GPCR Ki 7.79 WOMBAT-PK
Histamine H2 receptor GPCR Ki 6.25 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 6 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 5.58 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.00 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.32 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.45 WOMBAT-PK
Beta-3 adrenergic receptor GPCR Ki 4.66 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 6.48 WOMBAT-PK
5-hydroxytryptamine receptor 1D GPCR Ki 6.48 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.54 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 5.79 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.17 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 7.54 WOMBAT-PK
Alpha-1D adrenergic receptor GPCR Ki 8.02 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 7.89 WOMBAT-PK
Kappa-type opioid receptor GPCR Ki 5.01 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.07 DRUG MATRIX
5-hydroxytryptamine receptor 5A GPCR Ki 6.84 WOMBAT-PK
5-hydroxytryptamine receptor 1E GPCR Ki 6.27 WOMBAT-PK
Epidermal growth factor receptor Kinase IC50 4.40 DRUG MATRIX
Potassium channel subfamily K member 2 Ion channel IC50 5.33 CHEMBL
Tyrosine-protein kinase Fyn Kinase IC50 5.10 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.71 DRUG MATRIX
Histone deacetylase 6 Enzyme IC50 5.25 CHEMBL
Substance-K receptor GPCR Ki 5.13 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 5.05 DRUG MATRIX
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.43 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 5.78 CHEMBL
Androgen receptor Transcription factor Ki 6.10 CHEMBL
Trypanothione reductase Enzyme Ki 4.67 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 7.72 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 6.06 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 7.01 DRUG MATRIX
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 8.10 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.80 IUPHAR
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.77 CHEMBL
Adenylate cyclase Enzyme IC50 7.10 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.62 CHEMBL
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 Enzyme IC50 4.82 CHEMBL

External reference:

IDSource
4019762 VUID
N0000147853 NUI
D00791 KEGG_DRUG
146-56-5 SECONDARY_CAS_RN
4017723 VANDF
4019762 VANDF
C0016368 UMLSCUI
CHEBI:5123 CHEBI
CHEMBL726 ChEMBL_ID
CHEMBL1448187 ChEMBL_ID
D005476 MESH_DESCRIPTOR_UI
DB00623 DRUGBANK_ID
204 IUPHAR_LIGAND_ID
946 INN_ID
S79426A41Z UNII
3372 PUBCHEM_CID
203207 RXNORM
4348 MMSL
4750 MMSL
d00237 MMSL
001473 NDDF
001476 NDDF
372730004 SNOMEDCT_US
41365009 SNOMEDCT_US
61678008 SNOMEDCT_US
S79426A41Z INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0121-0653 SOLUTION, CONCENTRATE 5 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0121-0654 ELIXIR 0.50 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1788 TABLET, FILM COATED 1 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1789 TABLET, FILM COATED 2.50 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1790 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1791 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-6003 TABLET, FILM COATED 1 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-6004 TABLET, FILM COATED 2.50 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-6005 TABLET, FILM COATED 5 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-6006 TABLET, FILM COATED 10 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7157 TABLET, FILM COATED 1 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7158 TABLET, FILM COATED 2.50 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7159 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7160 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-725 TABLET 1 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-725 TABLET 1 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-726 TABLET 2.50 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-726 TABLET 2.50 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-727 TABLET 5 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-727 TABLET 5 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-728 TABLET 10 mg ORAL ANDA 14 sections
FLUPHENAZINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-728 TABLET 10 mg ORAL ANDA 14 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-889 TABLET, FILM COATED 1 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-889 TABLET, FILM COATED 1 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-890 TABLET, FILM COATED 2.50 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-890 TABLET, FILM COATED 2.50 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-891 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-891 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-892 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Fluphenazine Hydrochoride Human Prescription Drug Label 1 16571-892 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections