Primaquine

Structural formula
	1: 1 mixture of the stereoisomers - ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Primaquine
other names	(±) - N 4 - (6-methoxyquinolin-8-yl) pentane-1,4-diamine; ( RS ) - N 4 - (6-Methoxyquinolin-8-yl) pentane-1,4-diamine; DL - N 4 - (6-methoxyquinolin-8-yl) pentane-1,4-diamine; Latin : Primaquinum;
Molecular formula	C 15 H 21 N 3 O
Brief description	viscous liquid (primaquine) ; orange-red, odorless powder with a bitter taste (primaquine bisphosphonate) ;
External identifiers / databases
EC number	201-987-2
ECHA InfoCard	100.001.807
PubChem	4908
ChemSpider	4739
DrugBank	DB01087
Wikidata	Q419834
Drug information
ATC code	P01 BA03
Drug class	Antiprotozoal drugs
properties
Molar mass	259.35 g · mol -1
Melting point	<25 ° C
boiling point	175-179 ° C (26.7 Pa )
solubility	soluble in diethyl ether (primaquine) ; soluble in water, practically insoluble in ethanol , chloroform or diethyl ether (primaquine bisphosphonate) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Bisphosphate; danger
H and P phrases	H: 301
	P: 301 + 310
Toxicological data	100 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Primaquine is a medicinal substance that is suitable for combating and treating malaria , especially tertian malaria.

It has been used since 1926 and is particularly effective against the extra-erythrocytic parasite stages, especially with Plasmodium vivax . The interaction of primaquine with the double-stranded DNA of the plasmodia leads to an inhibition of protein biosynthesis. The intake is limited to 2 weeks. Side effects are very rare, but serious in the case of glucose-6-phosphate dehydrogenase deficiency (G6PD deficiency). In addition, taking primaquine can lead to anemia or headaches .

The active ingredient is approved under the trade names A-PQ ^® NL and Primaquine ^® CDN (as of October 2009).

Side effects

During the Second World War it was noticed that African American soldiers reacted more frequently to the malaria drug primaquine with a breakdown of red blood cells (haemolysis). After the war, a defect in the enzyme glucose-6-phosphate dehydrogenase was recognized as the cause . It also found that people from the Mediterranean area can also be affected. In addition, serious side effects are known from an interaction with grapefruit.

literature

JK Baird, SL Hoffman: Primaquine therapy for malaria. In: Clin Infect Dis . 39, 2004, pp. 1336-1345. PMID 15494911
Heinz Lüllmann, Klaus Mohr, Martin Wehling, Lutz Hein: Pharmacology and toxicology: Understanding drug effects - using drugs in a targeted manner. Thieme, Stuttgart.

Individual evidence

↑ ^a ^b ^c Entry on primaquine. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
^ ^A ^b Poisons Information Monograph (PIM) for Primaquine , accessed November 2, 2014.
↑ ^a ^b Entry on primaquine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Datasheet Primaquine bisphosphate from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
↑ AS Alving, PE Ccarson et al.: Enzymatic deficiency in primaquine-sensitive erythrocytes. In: Science. Volume 124, Number 3220, September 1956, pp. 484-485. PMID 13360274 .
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[RÖMPP_Online-1] Entry on primaquine. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

[Inchem-2] A ^b Poisons Information Monograph (PIM) for Primaquine , accessed November 2, 2014.

[ChemIDplus-3] Entry on primaquine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-4] Datasheet Primaquine bisphosphate from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[paper0-5] AS Alving, PE Ccarson et al.: Enzymatic deficiency in primaquine-sensitive erythrocytes. In: Science. Volume 124, Number 3220, September 1956, pp. 484-485. PMID 13360274 .

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