Details
Stereochemistry | ACHIRAL |
Molecular Formula | C29H32Cl2N6.H3O4P |
Molecular Weight | 633.506 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.ClC1=CC=C2C(=C1)N=CC=C2N3CCN(CCCN4CCN(CC4)C5=C6C=CC(Cl)=CC6=NC=C5)CC3
InChI
InChIKey=KATNPMSTHHZOTK-UHFFFAOYSA-N
InChI=1S/C29H32Cl2N6.H3O4P/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;1-5(2,3)4/h2-9,20-21H,1,10-19H2;(H3,1,2,3,4)
Molecular Formula | H3O4P |
Molecular Weight | 97.9952 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C29H32Cl2N6 |
Molecular Weight | 535.511 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20547801Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20937779 | https://clinicaltrials.gov/ct2/show/NCT02788864 | https://www.ncbi.nlm.nih.gov/pubmed/18180357 | https://clinicaltrials.gov/ct2/show/NCT02590627
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20547801
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20937779 | https://clinicaltrials.gov/ct2/show/NCT02788864 | https://www.ncbi.nlm.nih.gov/pubmed/18180357 | https://clinicaltrials.gov/ct2/show/NCT02590627
Piperaquine is a bisquinoline antimalarial drug that was first synthesized in the 1960s and used extensively in China and Indochina as prophylaxis and treatment during the next 20 years. Usage declined in the 1980s as piperaquine-resistant strains of P. falciparum arose and artemisinin-based antimalarials became available. However, during the next decade, piperaquine was rediscovered by Chinese scientists as one of a number of compounds suitable for combination with an artemisinin derivative. The rationale for such artemisinin combination therapies (ACTs) was to provide an inexpensive, short-course treatment regimen with a high cure rate and good tolerability that would reduce transmission and protect against the development of parasite resistance. Piperaquine is characterized by slow absorption and a long biological half-life, making it a good partner drug with artemisinin derivatives which are fast acting but have a short biological half-life.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20937779 |
29.0 nM [IC50] | ||
Target ID: CHEMBL613013 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18180357 |
29.1 nM [IC50] | ||
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20547801 |
48.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[Factors affecting the in vitro microtest for drug sensitivity of Plasmodium falciparum]. | 2003 |
|
Measurement of piperaquine in plasma by liquid chromatography with ultraviolet absorbance detection. | 2003 Jul 5 |
|
Automated solid-phase extraction method for the determination of piperaquine in whole blood by rapid liquid chromatography. | 2003 Oct |
|
CV8, a new combination of dihydroartemisinin, piperaquine, trimethoprim and primaquine, compared with atovaquone-proguanil against falciparum malaria in Vietnam. | 2004 Feb |
|
Safety evaluation of fixed combination piperaquine plus dihydroartemisinin (Artekin) in Cambodian children and adults with malaria. | 2004 Jan |
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Dihydroartemisinin-piperaquine against multidrug-resistant Plasmodium falciparum malaria in Vietnam: randomised clinical trial. | 2004 Jan 3 |
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A randomized, controlled study of a simple, once-daily regimen of dihydroartemisinin-piperaquine for the treatment of uncomplicated, multidrug-resistant falciparum malaria. | 2005 Aug 15 |
|
Artemisinin-based combination therapies for uncomplicated malaria. | 2005 Feb 21 |
|
Intermittent presumptive treatment for malaria. | 2005 Jan |
|
Efficacy comparison between anti-malarial drugs in Africans presenting with mild malaria in the Central Republic of Africa: a preliminary study. | 2005 Mar |
|
Development and validation of an automated solid phase extraction and liquid chromatographic method for the determination of piperaquine in urine. | 2006 Apr 11 |
|
Characterization of human urinary metabolites of the antimalarial piperaquine. | 2006 Dec |
|
Safety and efficacy of dihydroartemisinin/piperaquine (Artekin) for the treatment of uncomplicated Plasmodium falciparum malaria in Rwandan children. | 2006 Dec |
|
Identification of an isomer impurity in piperaquine drug substance. | 2006 Dec 1 |
|
Efficacy and effectiveness of dihydroartemisinin-piperaquine versus artesunate-mefloquine in falciparum malaria: an open-label randomised comparison. | 2006 Jun 24 |
|
Treatment of falciparum malaria in the age of drug resistance. | 2006 Oct-Dec |
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Dihydroartemisinin-piperaquine versus artesunate-amodiaquine: superior efficacy and posttreatment prophylaxis against multidrug-resistant Plasmodium falciparum and Plasmodium vivax malaria. | 2007 Apr 15 |
|
Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed? | 2007 Feb 16 |
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Activity of piperaquine and other 4-aminoquinoline antiplasmodial drugs against chloroquine-sensitive and resistant blood-stages of Plasmodium falciparum. Role of beta-haematin inhibition and drug concentration in vacuolar water- and lipid-phases. | 2007 Jun 15 |
|
In vitro activity of ferroquine (SSR 97193) against Plasmodium falciparum isolates from the Thai-Burmese border. | 2007 Jun 27 |
|
Large-scale malaria survey in Cambodia: novel insights on species distribution and risk factors. | 2007 Mar 27 |
|
Two fixed-dose artemisinin combinations for drug-resistant falciparum and vivax malaria in Papua, Indonesia: an open-label randomised comparison. | 2007 Mar 3 |
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Artemether-lumefantrine versus dihydroartemisinin-piperaquine for treatment of malaria: a randomized trial. | 2007 May 18 |
|
Dose ranging studies of new artemisinin-piperaquine fixed combinations compared to standard regimens of artemisisnin combination therapies for acute uncomplicated falciparum malaria. | 2007 Nov |
|
Pharmacokinetics of piperaquine after single and multiple oral administrations in healthy volunteers. | 2007 Oct |
|
Efficacy and safety of dihydroartemisinin-piperaquine. | 2007 Sep |
|
Two years after the Fourth External Review: TDR moves forward with a new vision and strategy. | 2008 |
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[Efficacy of dihydroartemisinin-piperaquine and artemether-lumefantrine in the treatment of uncomplicated falciparum malaria in Hainan, China]. | 2008 Feb 28 |
|
Efficacy of Artequick versus artesunate-mefloquine in the treatment of acute uncomplicated falciparum malaria in Thailand. | 2008 Jan |
|
No PfATPase6 S769N mutation found in Plasmodium falciparum isolates from China. | 2008 Jul 8 |
|
Quantification of the antimalarial piperaquine in plasma. | 2008 May |
|
Revisiting the design of phase III clinical trials of antimalarial drugs for uncomplicated Plasmodium falciparum malaria. | 2008 Nov 18 |
|
Modelling the impact of artemisinin combination therapy and long-acting treatments on malaria transmission intensity. | 2008 Nov 25 |
|
A single LC-tandem mass spectrometry method for the simultaneous determination of 14 antimalarial drugs and their metabolites in human plasma. | 2009 Apr 1 |
|
Plasmodium berghei ANKA: selection of resistance to piperaquine and lumefantrine in a mouse model. | 2009 Jul |
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A randomized, controlled trial of artemisinin-piperaquine vs dihydroartemisinin-piperaquine phosphate in treatment of falciparum malaria. | 2009 Jun |
|
Antimalarial drug susceptibility of Plasmodium vivax in the Republic of Korea. | 2009 Jun |
|
A systematic review and meta-analysis of evidence for correlation between molecular markers of parasite resistance and treatment outcome in falciparum malaria. | 2009 May 4 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02788864
Primaquine (One tablet contains 13.2mg primaquine disphosphate/7.5mg base. Weight based regimen: 0.25mg base/kg) for 14 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20937779
he antimalarial susceptibilities of P. ovale and P. malariae isolates were measured using a protocol modified from the WHO microtes Venous blood (5 ml) was collected by venipuncture, and after removal of host white blood cells using a CF11 column, 2 ml of packed infected red blood cells (IRBC) were divided as follows: 1 ml was cryopreserved in glycerolyte, 200 mkl was spotted onto filter paper, and 800 _l was used for the in vitro drug susceptibility assay. Two hundred microliters of a 2% hematocrit blood medium mixture (BMM) consisting of McCoy’s 5A medium. and 20% AB_ human serum was added to each well of predosed drug plates; the drug plates contained 11 serial concentrations (2-fold dilutions) of the antimalarials, with maximum concentrations of 5,910 nM for chloroquine, 557 nM for amodiaquine, 93 nM for artesunate, 338 nM for mefloquine, 87 nM for pyronaradine, and 769 nM for piperaquine. A candle jar was used to mature the parasites at 37.5°C for 15 to 56 h. Incubation was stopped when >40% of ring stage parasites had matured into mature schizonts in the drug-free control. Preliminary studies demonstrated that once the 40% schizont threshold had been reached, further incubation did not increase the final count.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:15:07 GMT 2023
by
admin
on
Sat Dec 16 15:15:07 GMT 2023
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Record UNII |
5A17BAT3GK
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Record Status |
Validated (UNII)
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Record Version |
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