fluphenazine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ┬ÁM/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

Approvals:

DateAgencyCompanyOrphan
Sept. 9, 1959 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AB02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA EPC N0000175746 Phenothiazine
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
CHEBI has role CHEBI:37930 phenothiazine antipsychotic drug
CHEBI has role CHEBI:48561 dopaminergic antagonist
MeSH PA D014149 Tranquilizing Agents

Drug Use (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

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
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 2B GPCR Ki 7.60 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.46 DRUG MATRIX
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
Beta-3 adrenergic receptor GPCR Ki 4.66 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.79 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.17 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.02 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.00 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.07 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.40 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.10 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.71 DRUG MATRIX
Substance-K receptor GPCR Ki 5.13 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 5.05 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 9.37 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.19 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 8.10 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 8.04 WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 7.89 WOMBAT-PK
D(4) dopamine receptor GPCR Ki 7.54 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR Ki 7.54 WOMBAT-PK
Histamine H1 receptor GPCR Ki 7.79 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 7.89 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7.09 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.46 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 7.65 WOMBAT-PK
5-hydroxytryptamine receptor 1E GPCR Ki 6.27 WOMBAT-PK
5-hydroxytryptamine receptor 5A GPCR Ki 6.84 WOMBAT-PK
5-hydroxytryptamine receptor 1D GPCR Ki 6.48 WOMBAT-PK
5-hydroxytryptamine receptor 1B GPCR Ki 6.48 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 6.45 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 6 WOMBAT-PK
Histamine H2 receptor GPCR Ki 6.25 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.84 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.50 WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.43 CHEMBL
Mu-type opioid receptor GPCR Ki 5.07 DRUG MATRIX
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
Trypanothione reductase Enzyme Ki 4.67 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.77 CHEMBL
Androgen receptor Transcription factor Ki 6.10 CHEMBL
Adenylate cyclase Enzyme IC50 7.10 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 5.78 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.62 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.80 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 8.10 IUPHAR

External reference:

IDSource
D005476 MESH_DESCRIPTOR_UI
4019762 VUID
N0000147853 NUI
C0016368 UMLSCUI
D00791 KEGG_DRUG
41365009 SNOMEDCT_US
4496 RXNORM
372730004 SNOMEDCT_US
4019762 VANDF
d00237 MMSL
001473 NDDF
CHEMBL726 ChEMBL_ID
DB00623 DRUGBANK_ID
CHEMBL1200792 ChEMBL_ID
S79426A41Z UNII
946 INN_ID
CHEBI:5123 CHEBI
146-56-5 SECONDARY_CAS_RN
CHEMBL1200951 ChEMBL_ID
CHEMBL1448187 ChEMBL_ID
3372 PUBCHEM_CID
204 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0121-0653 SOLUTION, CONCENTRATE 5 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0121-0654 ELIXIR 0.50 mg ORAL ANDA 12 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6004 TABLET, FILM COATED 1 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6009 TABLET, FILM COATED 2.50 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6074 TABLET, FILM COATED 5 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6097 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1788 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1789 TABLET, FILM COATED 2.50 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1790 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1791 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1436 TABLET, FILM COATED 1 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1437 TABLET, FILM COATED 2.50 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1438 TABLET, FILM COATED 5 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1439 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17856-0654 ELIXIR 0.50 mg ORAL ANDA 12 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-485 TABLET, FILM COATED 1 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-486 TABLET, FILM COATED 2.50 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-487 TABLET, FILM COATED 5 mg ORAL ANDA 11 sections
Fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-488 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0247 TABLET, FILM COATED 5 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0600 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63323-281 INJECTION, SOLUTION 2.50 mg INTRAMUSCULAR ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64725-1438 TABLET, FILM COATED 5 mg ORAL ANDA 10 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 64725-2810 INJECTION, SOLUTION 2.50 mg INTRAMUSCULAR ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-2465 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-0318 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-1496 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2583 TABLET, FILM COATED 2.50 mg ORAL ANDA 12 sections