| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Piperaquine targets the malaria parasite's digestive vacuole. It accumulates in the acidic vacuole and inhibits heme detoxification, preventing the formation of hemozoin (malaria pigment). This leads to accumulation of toxic free heme and parasite death. Its exact molecular target is not fully defined but may involve inhibition of hemoglobin digestion or heme polymerization.
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|---|---|
| ln Vitro |
Piperaquine tetraphosphate (IC50: 38.9 nM; range: 7.76-78.3 nM) exhibits high activity against all Cameroonian isolates and inhibits both chloroquine-sensitive and chloroquine-resistant isolates[1].
In vitro, piperaquine inhibits the growth of Plasmodium falciparum with IC50 values in the nanomolar range. It is active against chloroquine-sensitive and chloroquine-resistant strains. It shows synergy with dihydroartemisinin and other artemisinin derivatives. It is less active against mature gametocytes. |
| ln Vivo |
In vivo, piperaquine tetraphosphate is effective in animal models of malaria. It reduces parasitemia and improves survival in Plasmodium berghei-infected mice. In humans, it is used in combination with dihydroartemisinin for uncomplicated P. falciparum malaria. It has a long half-life of approximately 3-4 weeks.
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| Enzyme Assay |
For non-cell assays, Plasmodium falciparum is cultured in human erythrocytes. Piperaquine is serially diluted in 96-well plates and added to parasite cultures. Parasite growth is measured by [3H]hypoxanthine incorporation or HRP2 ELISA. IC50 values are calculated from dose-response curves.
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| Cell Assay |
In cell assays, P. falciparum-infected erythrocytes are treated with piperaquine. Parasitemia is assessed by Giemsa-stained blood smears or flow cytometry. Hemozoin formation is measured by spectrophotometry. Stage-specific effects are assessed by synchronized cultures.
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| Animal Protocol |
In vivo animal protocols use mice infected with Plasmodium berghei or P. yoelii. Piperaquine tetraphosphate is administered orally at doses of 10-100 mg/kg. Parasitemia is monitored by blood smears. Survival is recorded. Pharmacokinetics are measured by LC-MS. Efficacy is compared with chloroquine and artesunate.
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| References |
[1]. asco LK, et al. In vitro activities of piperaquine and other 4-aminoquinolines against clinical isolates of Plasmodium falciparum in Cameroon. Antimicrob Agents Chemother. 2003 Apr;47(4):1391-4.
[2]. Salman S,et al. Pharmacokinetic comparison of two piperaquine-containing artemisinin combination therapies in Papua New Guinean children with uncomplicated malaria. Antimicrob Agents Chemother. 2012 Jun;56(6):3288-97. |
| Molecular Formula |
C29H44CL2N6O16P4
|
|---|---|
| Molecular Weight |
927.49
|
| Exact Mass |
926.114
|
| CAS # |
911061-10-4
|
| Related CAS # |
Piperaquine phosphate;85547-56-4;Piperaquine tetraphosphate tetrahydrate;915967-82-7;Piperaquine-d6 tetraphosphate;Piperaquine;4085-31-8
|
| PubChem CID |
53318025
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| Appearance |
Typically exists as solid at room temperature
|
| LogP |
1.715
|
| tPSA |
389.02
|
| Hydrogen Bond Donor Count |
12
|
| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
6
|
| Heavy Atom Count |
57
|
| Complexity |
704
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
OP(=O)(O)O.OP(=O)(O)O.OP(=O)(O)O.OP(=O)(O)O.ClC1C=CC2=C(N3CCN(CCCN4CCN(C5C=CN=C6C=C(C=CC=56)Cl)CC4)CC3)C=CN=C2C=1
|
| InChi Key |
OAKKJVUSSVZQRF-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C29H32Cl2N6.4H3O4P/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29;4*1-5(2,3)4/h2-9,20-21H,1,10-19H2;4*(H3,1,2,3,4)
|
| Chemical Name |
7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline;phosphoric acid
|
| 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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0782 mL | 5.3909 mL | 10.7818 mL | |
| 5 mM | 0.2156 mL | 1.0782 mL | 2.1564 mL | |
| 10 mM | 0.1078 mL | 0.5391 mL | 1.0782 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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