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

Stem definitionDrug idCAS RN
quinoline derivatives 3578 106635-80-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • arakoda
  • krintafel
  • tafenoquine succinate
  • tafenoquine
Tafenoquine, an 8-aminoquinoline antimalarial, is active against all the stages of Plasmodium species that include the hypnozoite (dormant stage) in the liver. Studies in vitro with the erythrocytic forms of Plasmodium falciparum suggest that tafenoquine may exert its effect by inhibiting hematin polymerization and inducing apoptotic like death of the parasite. In addition to its effect on the parasite, tafenoquine causes red blood cell shrinkage in vitro. The molecular target of tafenoquine is not known.
  • Molecular weight: 463.50
  • Formula: C24H28F3N3O3
  • CLOGP: 6.52
  • LIPINSKI: 1
  • HAC: 6
  • HDO: 2
  • TPSA: 78.63
  • ALOGS: -5.53
  • ROTB: 10

  • Status: ONP

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

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
July 20, 2018 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC P01BA07 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Aminoquinolines
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
CHEBI has role CHEBI:36335 trypanosomicidal agents
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:68495 type i programmed cell-death inducer
CHEBI has role CHEBI:70868 antileishmanial agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Malaria indication 61462000 DOID:12365

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.77 Basic
pKa2 2.92 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 100MG BASE ARAKODA 60 DEGREES PHARMS N210607 Aug. 8, 2018 RX TABLET ORAL Aug. 8, 2021 NEW PRODUCT
EQ 100MG BASE ARAKODA 60 DEGREES PHARMS N210607 Aug. 8, 2018 RX TABLET ORAL July 20, 2023 NEW CHEMICAL ENTITY
EQ 150MG BASE KRINTAFEL GLAXOSMITHKLINE N210795 July 20, 2018 RX TABLET ORAL July 20, 2023 NEW CHEMICAL ENTITY
EQ 150MG BASE KRINTAFEL GLAXOSMITHKLINE N210795 July 20, 2018 RX TABLET ORAL July 20, 2025 INDICATED FOR THE RADICAL CURE (PREVENTION OF RELAPSE) OF PLASMODIUM VIVAX MALARIA IN PATIENTS AGED 16 YEARS AND OLDER WHO ARE RECEIVING APPROPRIATE ANTIMALARIAL THERAPY FOR ACUTE P. VIVAX INFECTION

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Plasmodium vivax Bacteria INHIBITOR UNKNOWN DRUG LABEL

External reference:

IDSource
D10490 KEGG_DRUG
106635-81-8 SECONDARY_CAS_RN
4037963 VANDF
C4719650 UMLSCUI
CHEBI:135752 CHEBI
CHEMBL2364635 ChEMBL_ID
CHEMBL298470 ChEMBL_ID
115358 PUBCHEM_CID
C055852 MESH_SUPPLEMENTAL_RECORD_UI
7835 INN_ID
DB06608 DRUGBANK_ID
262P8GS9L9 UNII
9722 IUPHAR_LIGAND_ID
2054023 RXNORM
286549 MMSL
287722 MMSL
34723 MMSL
d08853 MMSL
017662 NDDF
017663 NDDF
773181000 SNOMEDCT_US
773236009 SNOMEDCT_US
773237000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Krintafel HUMAN PRESCRIPTION DRUG LABEL 1 0173-0889 TABLET, FILM COATED 150 mg ORAL NDA 30 sections
Arakoda HUMAN PRESCRIPTION DRUG LABEL 1 71475-257 TABLET, FILM COATED 100 mg ORAL NDA 29 sections