Pamaquine

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Pamaquine
Pamaquine.svg
Systematic (IUPAC) name
N,N-diethyl-N'-(6-methoxyquinolin-8-yl)pentane-
1,4-diamine
Clinical data
Legal status ?
Identifiers
CAS number 491-92-9 N
ATC code None
PubChem CID 10290
ChemSpider 9868 YesY
UNII 99QVL5KPSU YesY
ChEMBL CHEMBL472698 YesY
Chemical data
Formula C19H29N3O 
Mol. mass 315.453 g/mol
 N (what is this?)  (verify)

Pamaquine is an 8-aminoquinoline drug used for the treatment of malaria. It is closely related to primaquine.

History[edit]

Pamaquine was the second synthetic antimalarial drug to be discovered (after methylene blue). It was synthesised by Schulemann, Schoenhoeffer and Wingler in 1924. In 1926, Roehl demonstrated that pamaquine was effective in treating malaria in birds, and introduced it into use in humans.[1]

A large trial of pamaquine performed by the Royal Army Medical Corps and the Indian Medical Corps in 1929 showed for the first time that it was possible to prevent relapse of vivax malaria.[2] Prior to this, it was understood that patients with vivax malaria would suffer from relapses, but there was no treatment that could prevent the relapses from occurring.

Adverse effects[edit]

Like primaquine, pamaquine causes haemolytic anaemia in patients with G6PD deficiency. Patients should therefore always be screened for G6PD deficiency prior to being prescribed pamaquine.

Uses[edit]

Pamaquine is effective against the hypnozoites of the relapsing malarias (P. vivax and P. ovale); and unlike primaquine, it is also very effective against the erythrocytic stages of all four human malarias. One small clinical trial of pamaquine as a causal prophylactic was disappointing[3] (whereas primaquine is an extremely effective causal prophylactic).

Dosing[edit]

Pamaquine is more toxic and less efficacious than primaquine. Pamaquine is therefore no longer used and the only drug currently recommended by the World Health Organization is primaquine.[4]

There is no established dosing for pamaquine. The following regimens have been used, but the optimal dosing is unknown:

  • 20mg twice daily for 21 days.[2]
  • 30mg once daily for 14 days.[5]
  • 30mg once daily for 5 days.[6]

Synonyms[edit]

  • Plasmochin
  • Plasmoquine[2]
  • Plasmaquine

References[edit]

  1. ^ Roehl W (1926). "Die Wirkung of Plasmochins auf die Vogelmalaria". Arch Schiffs-Tropenhyg 30 (Suppl 3): 311–318. 
  2. ^ a b c Manifold J (1931). "Report on a trial of plasmoquine and quinine in the treatment of benign tertian malaria". Journal of the Royal Army Medical Corps LVI (5): 321–338,410–423. 
  3. ^ Sweeney AW, Blackburn CRB, KH Rieckmann. (1 August 2004). "Short report: The activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains)". Am J Trop Med Hyg 71 (2): 187–189. PMID 15306708. 
  4. ^ World Health Organization (2010). Guidelines for the treatment of malaria (2nd ed.). Geneva, Switzerland: WHO Press. p. 194. 
  5. ^ Earle DP, Bigelow FS, Zubrod CG, Kane CA. (1947). "Studies on the chemotherapy of the human malarias. IX. Effect of pamaquine on the blood cells of man". Journal of clinical investigation 27 (3 Pt 1): 121–129. PMID 18860190. 
  6. ^ Sweeney AW, Blackburn CRB, Rieckmann KH (2004). "Short report: the activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains).". Am J Trop Med Hyg 71 (2): 187–9. PMID 15306708.