tafenoquine

Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria. With respect to acute malaria, it is used together with other medications to prevent relapse by Plasmodium vivax. It may be used to prevent all types of malaria. It is taken by mouth.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 470476706
Drug.image: Tafenoquine.svg
Drug.image_class: skin-invert-image
Drug.pronounce: ta fen' oh kwin
Drug.tradename: Krintafel, Arakoda, others
Drug.MedlinePlus: a618050
Drug.DailyMedID: Tafenoquine
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth
Drug.class: Antimalarial
Drug.ATC_prefix: P01
Drug.ATC_suffix: BA07
Drug.legal_AU: S4
Drug.legal_US: Rx-only
Drug.index2_label: as salt
Drug.CAS_number: 106635-80-7

via Wikipedia infobox

Chemical data

Formula: C24H28F3N3O3
Molecular weight: 463.5 g/mol
IUPAC name: 4-N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2018
Admin. routes: oral
Indications: malaria, Plasmodium vivax malaria, Plasmodium falciparum malaria, COVID-19

via ChEMBL · EBI

Research

404 papers

Tafenoquine and G6PD: a primer for clinicians.Journal of travel medicine · 2019
Tafenoquine: a toxicity overview.Expert opinion on drug safety · 2021
Tafenoquine.2012
Tafenoquine: the new kid on the block.Current opinion in infectious diseases · 2019
Tafenoquine.2006

via PubMed

Wikidata facts

Mass: 463.208

Show 3 more facts

chemical formula: C₂₄H₂₈F₃N₃O₃
canonical SMILES: CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC
Commons category: Tafenoquine

Sources (3)

via Wikidata · CC0

~4 min read

Article

10 sections

Contents

Medical use
Prevention
Treatment
Chemistry
Synthesis
History
Society and culture
Names
References
External links

Common side effects include vomiting, headache, and dizziness. Other side effects may include methemoglobinemia, trouble sleeping, and anaphylaxis. In people with G6PD deficiency, red blood cell breakdown may occur. Use in pregnancy is not recommended. Tafenoquine is in the 8-aminoquinoline family of medications. The mechanism of action is unclear but it is effective both in the liver and bloodstream. A possible mechanism of action and other novel perspectives have been published.