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)

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 52.41 32.73 16 939 11106 46674001
Accommodation disorder 48.08 32.73 8 947 347 46684760
Salivary hypersecretion 42.34 32.73 12 943 6433 46678674
Blood prolactin increased 40.96 32.73 10 945 3017 46682090
Sedation 37.57 32.73 15 940 22895 46662212
Torsade de pointes 34.84 32.73 12 943 12142 46672965
Suicide attempt 33.17 32.73 18 937 55018 46630089

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
Neuroleptic malignant syndrome 62.34 34.82 25 1428 16270 29934755
Extrapyramidal disorder 57.38 34.82 21 1432 10672 29940353
Priapism 56.47 34.82 17 1436 4726 29946299
Torsade de pointes 49.52 34.82 17 1436 7173 29943852
Sedation 48.71 34.82 21 1432 16352 29934673
Granulocytopenia 47.91 34.82 16 1437 6210 29944815
Schizophrenia 42.06 34.82 16 1437 9032 29941993
Salivary hypersecretion 41.10 34.82 15 1438 7551 29943474

Pharmacologic Action:

SourceCodeDescription
ATC N05AB02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA CS M0016525 Phenothiazines
FDA EPC N0000175746 Phenothiazine
CHEBI has role CHEBI:37930 phenothiazine antipsychotics
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:149553 anti-coronaviral agents
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

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
5-hydroxytryptamine receptor 2A GPCR Ki 8.04 WOMBAT-PK
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
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
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
CHEMBL1200951 ChEMBL_ID
CHEMBL1448187 ChEMBL_ID
CHEMBL1200792 ChEMBL_ID
DB00623 DRUGBANK_ID
D005476 MESH_DESCRIPTOR_UI
204 IUPHAR_LIGAND_ID
946 INN_ID
S79426A41Z UNII
67356 PUBCHEM_CID
203207 RXNORM
4348 MMSL
4750 MMSL
d00237 MMSL
001473 NDDF
001476 NDDF
372730004 SNOMEDCT_US
41365009 SNOMEDCT_US
61678008 SNOMEDCT_US

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 0781-1436 TABLET, FILM COATED 1 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1437 TABLET, FILM COATED 2.50 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1438 TABLET, FILM COATED 5 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1439 TABLET, FILM COATED 10 mg ORAL ANDA 16 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-002 TABLET, FILM COATED 1 mg ORAL ANDA 17 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-003 TABLET, FILM COATED 2.50 mg ORAL ANDA 17 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-004 TABLET, FILM COATED 5 mg ORAL ANDA 17 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-005 TABLET, FILM COATED 10 mg ORAL ANDA 17 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17856-0654 ELIXIR 0.50 mg ORAL ANDA 16 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-435 TABLET, FILM COATED 1 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-436 TABLET, FILM COATED 2.50 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-437 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-438 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-034 TABLET, FILM COATED 1 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-035 TABLET, FILM COATED 2.50 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-036 TABLET, FILM COATED 5 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43598-037 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-4740 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-458 TABLET, FILM COATED 1 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-459 TABLET, FILM COATED 2.50 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-460 TABLET, FILM COATED 5 mg ORAL ANDA 15 sections
Fluphenazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-461 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60219-1678 TABLET, FILM COATED 1 mg ORAL ANDA 17 sections
fluphenazine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60219-1679 TABLET, FILM COATED 2.50 mg ORAL ANDA 17 sections