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| Targets |
Primaquine's mechanism of action is not fully elucidated, but it binds to and alters the properties of protozoal DNA. It eliminates tissue (exo-erythrocytic) malarial infection, preventing the development of erythrocytic forms responsible for relapses in P. vivax and P. ovale malaria. Primaquine is active against late hepatic stages (hypnozoites, schizonts). It also inhibits protein transport (IC50: 50 μM) and vesicle budding in donor cell membranes.
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| ln Vitro |
In vitro, primaquine phosphate shows antiplasmodial activity against P. falciparum 3D7 (chloroquine-sensitive) strain with an IC50 of 71.11 ± 6.47 ng/mL and against RKL9 strain with 263.86 ± 5.68 ng/mL. It inhibits protein transport with an IC50 of 50 μM. Primaquine effectively counters all exoerythrocytic forms of parasites. The compound is active against late hepatic stages (hypnozoites, schizonts).
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| ln Vivo |
In vivo, primaquine phosphate is administered orally to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria. The drug eliminates tissue (exo-erythrocytic) malarial infection, preventing the development of erythrocytic forms responsible for relapses. It is used in conjunction with other antimalarial drugs.
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| Enzyme Assay |
The in vitro antiplasmodial activity of primaquine phosphate is assessed using P. falciparum cultures. Parasites are cultured in human erythrocytes in RPMI-1640 medium. Cultures are treated with various concentrations of primaquine phosphate for 48-72 hours. Parasite growth is assessed by measuring the incorporation of [³H]hypoxanthine or by microscopy using Giemsa-stained smears. The IC50 is determined from dose-response curves. For protein transport inhibition, cell-free vesicle budding assays are used with IC50 determination.
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| Cell Assay |
For cellular assays, P. falciparum-infected erythrocytes are cultured in appropriate media. Parasites are treated with various concentrations of primaquine phosphate (typically 0.1-1000 ng/mL) for 48-72 hours. Parasitemia is assessed by microscopy or flow cytometry. For mechanistic studies, the effect on DNA integrity can be assessed by comet assay or by measuring DNA fragmentation. The effect on protein transport can be studied using vesicle budding assays in cell-free systems.
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| Animal Protocol |
In vivo, primaquine phosphate is administered orally to patients or animal models. For malaria treatment, the recommended dose is 15-30 mg base daily for 14 days. In animal models, the compound is administered orally at various doses (typically 1-50 mg/kg). Efficacy is assessed by measuring parasite clearance in blood smears. In hypnozoite models, relapse prevention is assessed by monitoring for recurrence of infection over several weeks. Pharmacokinetic studies involve plasma concentration measurement by HPLC or LC-MS/MS.
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| ADME/Pharmacokinetics |
Primaquine phosphate has a molecular weight of 455.34 g/mol and a molecular formula of C15H27N3O9P2. It has a melting point of 205-206°C (dec.) and a boiling point of 451.1°C at 760 mmHg. The compound is an orange to reddish-brown solid powder. It is soluble in water. The logP is 1.698. The compound should be stored under appropriate conditions to maintain stability.
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| Toxicity/Toxicokinetics |
Primaquine phosphate has several adverse effects, including hemolytic anemia (especially in patients with G6PD deficiency), gastrointestinal disturbances (nausea, vomiting, abdominal pain), and methemoglobinemia. It is contraindicated in patients with G6PD deficiency, pregnancy, and active rheumatoid arthritis. The drug should be used with caution in patients with cardiovascular disease. G6PD screening is recommended before primaquine administration to prevent severe hemolytic reactions.
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| Additional Infomation |
Primaquine phosphate is a prescription antimalarial drug approved by the U.S. Food and Drug Administration (FDA) for the prevention of relapses of malaria caused by Plasmodium vivax. Malaria can be an opportunistic infection (OI) of HIV. Opportunistic infections are those that are more common or more severe in people with weakened immune systems (such as HIV-infected individuals) than in people with healthy immune systems. Primaquine phosphate is the phosphate form of primaquine, a synthetic 8-aminoquinoline derivative with antimalarial properties. Although its mechanism of action is not fully understood, primaquine binds to and alters the properties of the protozoan DNA. The drug clears tissue (exocytic stage) Plasmodium infection, thereby preventing the development of erythrocytic Plasmodium parasites that lead to relapses of Plasmodium vivax and Plasmodium ovale. Primaquine is effective against late-stage hepatic Plasmodium (dormant zoan, schizont). It is an oral aminoquinoline drug used to eradicate vivax malaria and ovale malaria and to prevent relapse after treatment with blood schizonticides. It has also been used to prevent the transmission of falciparum malaria by returning personnel to areas where malaria may re-enter. Adverse reactions include anemia and gastrointestinal disturbances. (Excerpt from Martindale Pharmacopoeia, 30th edition, p. 404)
See also: primaquine (containing the active ingredient); chloroquine phosphate; primaquine phosphate (ingredient). Primaquine phosphate is an FDA-approved antimalarial drug used for radical cure and prevention of relapse of P. vivax and P. ovale malaria. It is the only drug that eliminates hypnozoites, the dormant liver stage parasites responsible for relapse. Primaquine was first introduced in 1950 and remains an essential medicine for malaria elimination efforts. It is included on the World Health Organization's List of Essential Medicines. The drug is also being studied for its potential in other parasitic infections and for its immunomodulatory effects. |
| Molecular Formula |
C15H24N3O5P
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| Molecular Weight |
357.34
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| Exact Mass |
455.122
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| CAS # |
63-45-6
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| Related CAS # |
Primaquine;90-34-6;Primaquine-d3 diphosphate
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| PubChem CID |
6135
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| Appearance |
Orange to reddish brown solid powder
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| Boiling Point |
451.1ºC at 760 mmHg
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| Melting Point |
205-206 °C (dec.)(lit.)
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| Flash Point |
226.6ºC
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| LogP |
1.698
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| Hydrogen Bond Donor Count |
8
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
312
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| Defined Atom Stereocenter Count |
0
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| SMILES |
P(=O)(O[H])(O[H])O[H].P(=O)(O[H])(O[H])O[H].O(C([H])([H])[H])C1C([H])=C2C([H])=C([H])C([H])=NC2=C(C=1[H])N([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]
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| InChi Key |
GJOHLWZHWQUKAU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
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| Chemical Name |
4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
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| Synonyms |
Primaquine (Diphosphate); PRIMAQUINE PHOSPHATE; Primaquine Phosphate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~549.04 mM)
H2O : ~25 mg/mL (~54.90 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 50 mg/mL (109.81 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7985 mL | 13.9923 mL | 27.9846 mL | |
| 5 mM | 0.5597 mL | 2.7985 mL | 5.5969 mL | |
| 10 mM | 0.2798 mL | 1.3992 mL | 2.7985 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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