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| | Primaquine diphosphate Basic information |
| Product Name: | Primaquine diphosphate | | Synonyms: | 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline diphosphate salt;PRIMAQUINEPHOSPHATE,USP;4-pentanediamine, n(sup 4)-(6-methoxy-8-quinolinyl)- phosphate;8-((4-amino-1-methylbutyl)amino)-6-methoxy-quinolin phosphate;Primaquine diphosphate salt, 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline diphosphate salt;1,4-Pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, phosphate (1:2);N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine phosphoric acid;Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, phosphate (1:2) | | CAS: | 63-45-6 | | MF: | C15H27N3O9P2 | | MW: | 455.34 | | EINECS: | 200-560-8 | | Product Categories: | Amines;Heterocycles;APIS;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 63-45-6.mol |  |
| | Primaquine diphosphate Chemical Properties |
| Melting point | 205-206 °C (dec.)(lit.) | | storage temp. | 2-8°C | | solubility | water: soluble50mg/mL, clear, orange to red | | form | neat | | Water Solubility | moderately soluble | | Merck | 13,7833 | | BRN | 3812133 | | BCS Class | 1 (CLogP), 3
(LogP) | | Stability: | Stable. Incompatible with strong oxidizing agents. | | CAS DataBase Reference | 63-45-6(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 45 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | VA9660000 | | F | 10 | | HazardClass | 6.1(b) | | PackingGroup | III | | HS Code | 29334900 |
| | Primaquine diphosphate Usage And Synthesis |
| Chemical Properties | orange powder | | Uses | Antimalarial. | | Uses | acetylcholinesterase inhibitor | | Uses | Primaquine diphosphate is an established antimalarial drug used in the treatment of persistent liver forms of P. vivax or P. ovale infection for its ability to kill late-stage gametocytes and hypnozoites. In historical terms, this aminoquinoline was the stimulus for the discovery of glucose-6-phosphate (G6P) dehydrogenase deficiency as it induced hemolytic anemia in patients lacking the G6P-metabolizing enzyme.
| | Brand name | Primaquine (Sanofi Aventis). | | Biological Activity | primaquine, an 8-aminoquinoline, is introduced as a curative antimalarial agent in 1950. since then, the drug has been applied extensively to against the exoerythrocytic stage of malaria. it is demonstrated tthat primaquine, by binding to nucleic acids, could therefore block protein synthesis, alter lipid synthesis and interact with biological membranes. [1] | | Clinical Use |
Treatment of malaria (Plasmodium vivax and
Plasmodium ovale), in combination with chloroquine
Treatment of Pneumocystis jiroveci pneumonia
(PCP), in combination with clindamycin | | in vitro | chicken embryo cells (cec) model were adopted to investigate the effect of primaquine on newcastle disease virus replication. it was found that virus-induced hemadsorption was inhibited by primaquine in a dose-dependent manner and was completely suppressed by primaquine 250 g/ml. viral ribonucleic acid (rna) synthesis was found to be suppressed when primaquine was added early in the virus replication cycle. whereas, when the drug was added late in the cycle, rna synthesis was stimulation. [1] | | in vivo | primaquine liposomes were labelled by 99mtc and injected intravenously to swiss albino mice. after injection, the major accumulation organ of liposomes was liver followed by spleen, pancreas, lungs and the others. findings also suggested that primaquine could block the eradication of the parasites and prevent relapse by destruction of the exoerythrocytic liver stages. [2] | | Drug interactions | Potentially hazardous interactions with other drugs
Antimalarials: avoid concomitant use with
artemether/lumefantrine. | | Metabolism | Rapidly metabolised in the liver. Its major metabolite
carboxyprimaquine accumulates in the plasma on
repeated dosage but possesses less antimalarial activity
than the parent compound.
Little unchanged drug is excreted in the urine. | | Purification Methods | It forms yellow crystals from 90% aqueous EtOH and is moderately soluble in H2O. The oxalate salt has m 182.5-185o (from 80% aqueous EtOH), and the free base is a viscous liquid b 165-170o/0.002mm, 175-177o/2mm. [Elderfield et al. J Am Chem Soc 68 1526 1964, Elderfield et al. J Am Chem Soc 77 4817 1955, Beilstein 22 III/IV 5817.] | | references | [1]burdick jr and durand dp. primaquine diphosphate: inhibition of newcastle disease virus replication. antimicrob agents ch. 1974 oct 15; 6(4): 460-4.
[2]aricat b, ozert ay, ercans mt and hincalt aa. characterization, in vitro and in vivo studies on primaquine diphosphate liposomes. j. microencapsulation. 1995; 12(5): 469-85.
[3]soto j, toledo j, rodriquez m, sanchez j, herrera r, padilla j and berman j. double-blind, randomized, placebo-controlled assessment of chloroquine/primaquine prophylaxis for malaria in nonimmune colombian soldiers. clin infect dis. 1999 jul; 29: 199-201. |
| | Primaquine diphosphate Preparation Products And Raw materials |
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