Pamaquine

Pamaquine

Systematic (IUPAC) name
N,N-diethyl-N'-(6-methoxyquinolin-8-yl)pentane- 1,4-diamine
Clinical data
Identifiers
CAS Registry Number	491-92-9 N
ATC code	None
PubChem	CID 10290
ChemSpider	9868 Y
UNII	99QVL5KPSU Y
ChEMBL	CHEMBL472698 Y
Chemical data
Formula	C19H29N3O
Molecular mass	315.453 g/mol
SMILES O(c1cc(NC(C)CCCN(CC)CC)c2ncccc2c1)C
InChI InChI=1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3  Y Key:QTQWMSOQOSJFBV-UHFFFAOYSA-N  Y
N (what is this?)  (verify)

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

History

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

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

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).

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]

Synonyms

• Plasmochin
• Plasmoquine^[2]
• Plasmaquine

References

1. ↑ Roehl W (1926). "Die Wirkung of Plasmochins auf die Vogelmalaria". Arch Schiffs-Tropenhyg 30 (Suppl 3): 311–318. 
2. ↑ 2.0 2.1 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.