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

Stem definitionDrug idCAS RN
2740 117-89-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • trifluoperazine
  • trifluoperazin
  • trifluoromethylperazine
  • trifluoroperazine
  • trifluperazine
  • triflurin
  • triperazine
  • trifluoperazine hydrochloride
  • trifluoperazine dihydrochloride
  • trifluoperazine HCl
  • flupazine
A phenothiazine with actions similar to CHLORPROMAZINE. It is used as an antipsychotic and an antiemetic.
  • Molecular weight: 407.50
  • Formula: C21H24F3N3S
  • CLOGP: 4.89
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 9.72
  • ALOGS: -4.67
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
20 mg O
8 mg P
20 mg R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 50 mg/mL Benet LZ, Broccatelli F, Oprea TI

Approvals:

DateAgencyCompanyOrphan
April 16, 1959 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AB06 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with piperazine structure
FDA EPC N0000175746 Phenothiazine
FDA CS M0016525 Phenothiazines
MeSH PA D000932 Antiemetics
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 D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:37930 phenothiazine antipsychotic drug
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Anxiety indication 48694002
Schizophrenia indication 58214004 DOID:5419
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Cirrhosis of liver contraindication 19943007 DOID:5082
Glaucoma contraindication 23986001 DOID:1686
Orthostatic hypotension contraindication 28651003
Retinal disorder contraindication 29555009 DOID:5679
Alcoholic liver damage contraindication 41309000
Low blood pressure contraindication 45007003
Chronic hepatitis contraindication 76783007 DOID:2237
Epilepsy contraindication 84757009 DOID:1826
Tardive dyskinesia contraindication 102449007
Diminished sweating contraindication 111980002
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
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
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.74 Basic
pKa2 4.74 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 8.84 PDSP CHEMBL
5-hydroxytryptamine receptor 6 GPCR Ki 6.85 PDSP
D(3) dopamine receptor GPCR ANTAGONIST Ki 9.25 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 6.54 PDSP
D(4) dopamine receptor GPCR ANTAGONIST Ki 7.38 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 6.00 PDSP
Alpha-2C adrenergic receptor GPCR Ki 6.41 PDSP
Alpha-2B adrenergic receptor GPCR Ki 6.79 PDSP
Alpha-2A adrenergic receptor GPCR Ki 6.18 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 6.02 PDSP
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 7.90 IUPHAR
Histamine H1 receptor GPCR ANTAGONIST Ki 7.20 IUPHAR
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 6.40 IUPHAR
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.29 DRUG MATRIX
Multidrug resistance protein 1 Transporter Ki 5.19 CHEMBL
Emopamil-binding protein-like Unclassified Ki 8.41 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.82 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.30 CHEMBL
DNA-dependent protein kinase catalytic subunit Kinase IC50 4 CHEMBL
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Enzyme Ki 8.10 CHEMBL
Calmodulin Cytosolic other Kd 6 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 7.62 PDSP
Trypanothione reductase Enzyme Ki 4.64 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Kd 8.98 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.85 CHEMBL
C-8 sterol isomerase Enzyme Ki 6.30 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 7.53 CHEMBL
NS3 Enzyme IC50 6.15 CHEMBL
Beta-glucuronidase Enzyme IC50 5.11 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.39 CHEMBL
Lysozyme C-1 Enzyme IC50 5.05 CHEMBL
D(2) dopamine receptor GPCR Kd 9.27 CHEMBL

External reference:

IDSource
4019957 VUID
N0000148042 NUI
C0040979 UMLSCUI
D00799 KEGG_DRUG
214IZI85K3 UNII
718 INN_ID
440-17-5 SECONDARY_CAS_RN
71699007 SNOMEDCT_US
4019957 VANDF
10800 RXNORM
373524005 SNOMEDCT_US
d00890 MMSL
004590 NDDF
CHEMBL422 ChEMBL_ID
DB00831 DRUGBANK_ID
CHEMBL1710 ChEMBL_ID
CHEBI:45951 CHEBI
CHEMBL1257040 ChEMBL_ID
D014268 MESH_DESCRIPTOR_UI
5566 PUBCHEM_CID
214 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2401 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2402 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2405 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2410 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8028 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8032 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8034 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-8036 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0494 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0495 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0496 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0497 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
TRIFLUOPERAZINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-305 TABLET, FILM COATED 2 mg ORAL ANDA 11 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-572 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-573 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-574 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-575 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0629 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0819 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-1960 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2015 TABLET, FILM COATED 1 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2095 TABLET, FILM COATED 2 mg ORAL ANDA 12 sections
Trifluoperazine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2106 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections