Primaquine diphosphate

SKU: orb1310236

Description

Primaquine diphosphate is the salt form of an 8-aminoquinoline antimalarial agent. It is primarily used in research to study the eradication of dormant liver-stage hypnozoites (Plasmodium vivax/ovale), preventing relapse, and is employed in both in vitro and in vivo models of hepatic-stage malaria.

Research Area

Infectious Disease & Virology

Key Properties

• CAS Number: 63-45-6
• MW: 455.34
• Purity: 99.82% (May vary between batches)
• Formula: C₁₅H₂₁N₃O·2H₃PO₄
• SMILES: CC(CCCN)Nc1c2c(cc(c1)OC)cccn2.OP(=O)(O)O.OP(=O)(O)O
• Target: Parasite,Antibiotic
• Solubility: H2O:83 mg/mL (182.28 mM);Ethanol:< 1 mg/mL (insoluble or slightly soluble);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (4.39 mM);DMSO:245 mg/mL (538.06 mM)

Bioactivity

• In Vivo:
  Primaquine effectively counters all exoerythrocytic forms of parasites and is used in conjunction with other antimalarial drugs to treat vivax and ovale malaria. It remains an efficacious malaria-blocking agent, exhibiting notable activity against the gametocytes of all human malaria, including multidrug-resistant strains of P. falciparum. The specific mechanism by which Primaquine eliminates P. falciparum and gametocytes is unclear, but studies suggest it involves disruptions to the parasite's mitochondrial metabolism, impairing coenzyme Q's role as an electron carrier in the respiratory chain, and potential generation of highly reactive metabolites leading to increased oxidative potential. Primaquine can block calcium-release-activated channels in rat megakaryocytes and may also act as an inhibitor of vesicular transport. It inhibits protein transport (IC50: 50 μM) and vesicle budding in donor cell membranes. Primaquine significantly suppresses the recycling of phagocytosed proteins to the plasma membrane and inhibits potassium channel currents by blocking muscarinic acetylcholine receptors. It also inhibits human erythrocyte membrane acetylcholinesterase (IC33: 30 μM) and affects the sodium channels in isolated rat ventricular muscle and myocytes.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Antibiotic, Parasite, parasitic, inhibit, Inhibitor, hepatic, malaria, late, latent, stages, tissue, Primaquine, Primaquine bisphosphate, Primaquine Diphosphate, Primaquine diphosphate, Primaquine phosphate, Primaquine Phosphate

Compound Identifiers

PubChem CID

6135