Primaquine Diphosphateantimalarial agent,blocks protein synthesis CAS# 63-45-6 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 63-45-6 | SDF | Download SDF |
| PubChem ID | 6135 | Appearance | Powder |
| Formula | C15H27N3O9P2 | M.Wt | 455.34 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Primaquine phosphate; Primaquine bisphosphate | ||
| Solubility | H2O : 50 mg/mL (109.81 mM; Need ultrasonic) | ||
| Chemical Name | 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid | ||
| SMILES | CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2.OP(=O)(O)O.OP(=O)(O)O | ||
| Standard InChIKey | GJOHLWZHWQUKAU-UHFFFAOYSA-N | ||
| Standard InChI | 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) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Primaquine is the only generally available anti-malarial that prevents relapse in vivax and ovale malaria, and the only potent gametocytocide in falciparum malaria. References: | |||||
Primaquine Diphosphate Dilution Calculator
Primaquine Diphosphate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1962 mL | 10.9808 mL | 21.9616 mL | 43.9232 mL | 54.904 mL |
| 5 mM | 0.4392 mL | 2.1962 mL | 4.3923 mL | 8.7846 mL | 10.9808 mL |
| 10 mM | 0.2196 mL | 1.0981 mL | 2.1962 mL | 4.3923 mL | 5.4904 mL |
| 50 mM | 0.0439 mL | 0.2196 mL | 0.4392 mL | 0.8785 mL | 1.0981 mL |
| 100 mM | 0.022 mL | 0.1098 mL | 0.2196 mL | 0.4392 mL | 0.549 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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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]
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]
Clinical trial: In a double-blind, randomized and placebo-controlled clinical trial, subjects were administered with chloroquine plus two primaquine diphosphate tablets (30 mg) daily or matching placebos in a two-to-one allocation. Chloroquine/primaquine treatment showed remarkable protective efficacy for a group of 100 subjects. Compared with that for the placebo treatment group of 51 subjects, chloroquine/primaquine exhibited inhibitory effect to 88% of all types malaria, 89% of P. falciparum malaria and 88% of P. vivax malaria. [3]
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.
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Analysis of quinocide in unprocessed primaquine diphosphate and primaquine diphosphate tablets using gas chromatography-mass spectrometry with supersonic molecular beams.[Pubmed:19108846]
J Chromatogr A. 2009 Jan 30;1216(5):824-9.
Malaria is one of the most widespread and deadly diseases on the planet. Every year, about 500 million new cases are diagnosed, and the annual death toll is about 3 million. Primaquine has strong antiparasitic effects against gametocytes and can therefore prevent the spread of the parasite from treated patients to mosquitoes. It is also used in radical cures and prevents relapse. Consequently, primaquine is an often-used drug. In this study the separation of unprocessed primaquine from the contaminant quinocide based on gas chromatography-mass spectrometry with supersonic molecular beam (SMB) is presented and 7.5 mg Primaquine Diphosphate tablets were analyzed. We present a novel method for fast determination of quinocide which is an isomer of primaquine as the main contaminant in unprocessed primaquine and in its medical form as tablets by gas chromatography-mass spectrometry with SMB (also named supersonic GC-MS). Supersonic GC-MS provides enhanced molecular ion without any ion source related peak tailing plus extended range of compounds amenable for GC-MS analysis. In addition, major isomer mass spectral effects were revealed in the mass spectra of primaquine and quinocide which facilitated the unambiguous identification of quinocide in primaquine tablets. Fast GC-MS analysis is demonstrated with less then 2 min elution time of the drug and its main contaminants.
Optimization of primaquine diphosphate tablet formulation for controlled drug release using the mixture experimental design.[Pubmed:22670808]
Pharm Dev Technol. 2013 Sep-Oct;18(5):1247-54.
A tablet formulation based on hydrophilic matrix with a controlled drug release was developed, and the effect of polymer concentrations on the release of Primaquine Diphosphate was evaluated. To achieve this purpose, a 20-run, four-factor with multiple constraints on the proportions of the components was employed to obtain tablet compositions. Drug release was determined by an in vitro dissolution study in phosphate buffer solution at pH 6.8. The polynomial fitted functions described the behavior of the mixture on simplex coordinate systems to study the effects of each factor (polymer) on tablet characteristics. Based on the response surface methodology, a tablet composition was optimized with the purpose of obtaining a Primaquine Diphosphate release closer to a zero order kinetic. This formulation released 85.22% of the drug for 8 h and its kinetic was studied regarding to Korsmeyer-Peppas model, (Adj-R(2) = 0.99295) which has confirmed that both diffusion and erosion were related to the mechanism of the drug release. The data from the optimized formulation were very close to the predictions from statistical analysis, demonstrating that mixture experimental design could be used to optimize Primaquine Diphosphate dissolution from hidroxypropylmethyl cellulose and polyethylene glycol matrix tablets.
Nature of the main contaminant in the drug primaquine diphosphate: SFC and SFC-MS methods of analysis.[Pubmed:17079107]
J Pharm Biomed Anal. 2007 Feb 19;43(3):937-44.
The drug Primaquine Diphosphate is used for causative treatment of malaria. Using HPLC-MS and GC-MS, this research group was previously able to show that the main contaminant of primaquine is the positional isomer quinocide [I. Brondz, D. Mantzilas, U. Klein, D. Ekeberg, E. Hvattum, M.N. Lebedeva, F.S. Mikhailitsyn, G.D. Soulimanov, J. Roe, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 800 (2004) 211-223; I. Brondz, U. Klein, D. Ekeberg, D. Mantzilas, E. Hvattum, H. Schultz, F. S. Mikhailitsyn, Asian J. Chem. 17 (2005) 1678-1688]. Primaquine and quinocide are highly toxic substances which can have a number of side effects upon use in medical treatment. A standard for quinocide is not typically commercially available. In the present work, supercritical fluid chromatography-mass spectrometry (SFC-MS) with two different columns was used to achieve a shorter analysis time for the separation between the positional isomers quinocide and primaquine in Primaquine Diphosphate and to elucidate additional information about differences in their MS fragmentation. Unlike using HPLC-MS, it was possible to achieve the differential fragmentation of positional isomers at branching points using the SFC-MS technique. The desired short analysis time was achieved using SFC equipped with a Discovery HS F5 column and the differential fragmentation of positional isomers during SFC-MS provides information on the differences in the structure of these substances. Using a Chiralpak AD-H chiral column, it was possible to resolve the enantiomers in primaquine and separate quinocide from those enantiomers.
