Structure via PubChem · Public domain (PubChem)
(RS)-primaquine
Sign in to saveAlso known as 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline, 6-methoxy-8-(4-amino-1-methylbutylamino)quinoline, primaquine
Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.
Chemical data
- Formula
- C15H21N3O
- Molecular weight
- 259.35 g/mol
- IUPAC name
- 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
- SMILES
- CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
- InChIKey
- INDBQLZJXZLFIT-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 60.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
22 papers- Primaquine-thiazolidinones block malaria transmission and development of the liver exoerythrocytic forms.Malaria journal · 2017
- Optimal balance of benefit versus risk for tafenoquine in the treatment of Plasmodium vivax malaria.Malaria journal · 2024
- Effects of primaquine and chloroquine on oxidative stress parameters in rats.Anais da Academia Brasileira de Ciencias · 2015
- Enantioselective pharmacokinetics of primaquine in healthy human volunteers.Drug metabolism and disposition: the biological fate of chemicals · 2015
- Association of G6PD status and haemolytic anaemia in patients receiving anti-malarial agents: a systematic review and meta-analysis.Malaria journal · 2023
via PubMed
Wikidata facts
- Mass
- 259.168462
Show 6 more facts
- chemical formula
- C₁₅H₂₁N₃O
- Commons category
- Primaquine
- canonical SMILES
- CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2
- World Health Organisation international non-proprietary name
- primaquine
- defined daily dose
- 15
- subject has role
- antimalarial
Sources (6)
via Wikidata · CC0
~7 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Malaria
- ''Pneumocystis'' pneumonia
- Special populations
- Adverse reactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Names
- Research
- References
- External links
Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.
Common side effects include nausea, vomiting, and stomach cramps. Primaquine should not be given to people with glucose-6-phosphate dehydrogenase (G6PD) deficiency due to the risk of red blood cell breakdown. It is often recommended that primaquine not be used during pregnancy. It may be used while breastfeeding if the baby is known not to have G6PD deficiency. The mechanisms of action are not entirely clear but are believed to involve effects on the malaria parasites' DNA.
Excerpted from Wikipedia’s “(RS)-primaquine” article, available under the CC BY-SA 4.0 licence.