Primaquine

Primaquine
Clinical data
Other namesprimaquine phosphate
AHFS/Drugs.comMonograph
MedlinePlusa607037
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability96%[1]
MetabolismLiver
Elimination half-life6 hours
Identifiers
  • (RS)-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.807 Edit this at Wikidata
Chemical and physical data
FormulaC15H21N3O
Molar mass259.353 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O(c1cc(NC(C)CCCN)c2ncccc2c1)C
  • InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3 checkY
  • Key:INDBQLZJXZLFIT-UHFFFAOYSA-N checkY
  (verify)

Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia.[2] 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.[2] It is an alternative treatment for Pneumocystis pneumonia together with clindamycin.[2][3] It is taken by mouth.[2]

Common side effects include nausea, vomiting, and stomach cramps.[2][4] Primaquine should not be given to people with glucose-6-phosphate dehydrogenase (G6PD) deficiency due to the risk of red blood cell breakdown.[4] It is often recommended that primaquine not be used during pregnancy.[5][6] It may be used while breastfeeding if the baby is known not to have G6PD deficiency.[6] The mechanisms of action is not entirely clear but is believed to involve effects on the malaria parasites' DNA.[2]

Primaquine was first made in 1946.[3] It is on the World Health Organization's List of Essential Medicines.[7][8] It is available as a generic medication.[2]

  1. ^ Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM (June 1985). "Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size". British Journal of Clinical Pharmacology. 19 (6): 745–750. doi:10.1111/j.1365-2125.1985.tb02709.x. PMC 1463857. PMID 4027117.
  2. ^ a b c d e f g "Primaquine Phosphate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 2 December 2016.
  3. ^ a b Vale N, Moreira R, Gomes P (March 2009). "Primaquine revisited six decades after its discovery". European Journal of Medicinal Chemistry. 44 (3): 937–953. doi:10.1016/j.ejmech.2008.08.011. hdl:10216/82052. PMID 18930565.
  4. ^ a b Arguin PM, Tan KR (2016). "Malaria - Chapter 3". In Brunette GW (ed.). CDC Health Information for International Travel 2016 (Yellow Book). CDC and Oxford University Press. ISBN 978-0-19-937915-6. Archived from the original on 2016-01-14.
  5. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 57. ISBN 9781284057560.
  6. ^ a b Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ (September 2006). "Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I". The American Journal of Tropical Medicine and Hygiene. 75 (3): 402–415. doi:10.4269/ajtmh.2006.75.402. PMID 16968913. Archived from the original on 2014-01-23.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.