Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C29H32ClN5O2.4H3O4P |
| Molecular Weight | 910.03 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O.COC1=NC2=C(NC3=CC(CN4CCCC4)=C(O)C(CN5CCCC5)=C3)C6=CC=C(Cl)C=C6N=C2C=C1
InChI
InChIKey=YKUQEKXHQFYULM-UHFFFAOYSA-N
InChI=1S/C29H32ClN5O2.4H3O4P/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35;4*1-5(2,3)4/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32);4*(H3,1,2,3,4)
Pyronaridine was developed in China and has been registered in that country since the 1980s. Outside China, none of the existing formulations is registered because of the failure to meet international regulatory standards. Pyronaridine is generally active against chloroquine-resistant parasites. Pyronaridine has been investigated for the treatment of Malaria. Pyronaridine targets hematin. Combination of pyronaridine with artesunate was indicated for the blood-stage treatment of both strains of malaria: P. falciparum and P. vivax. WHO currently recommends artesunate-pyronaridine in areas where other artemisinin-based combination therapies are failing.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Thieno[3,2-c]quinoline-4-yl-amines--synthesis and investigation of activity against malaria]. | 2006 Apr |
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| [Establishment of in vitro microtest for determining sensitivity of Plasmodium falciparum to pyronaridine]. | 2006 Apr 30 |
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| Activity of azithromycin or erythromycin in combination with antimalarial drugs against multidrug-resistant Plasmodium falciparum in vitro. | 2006 Dec |
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| Determination of the physicochemical properties of pyronaridine - a new antimalarial drug. | 2006 Jan |
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| Antimalarial activity of concanamycin A alone and in combination with pyronaridine. | 2006 Jul |
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| Treatment of falciparum malaria in the age of drug resistance. | 2006 Oct-Dec |
|
| Potentiation of antimalarial drug action by chlorpheniramine against multidrug-resistant Plasmodium falciparum in vitro. | 2006 Sep |
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| Potentiation of anti-epileptic drugs effectiveness by pyronaridine in refractory epilepsy. | 2007 |
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| [Benzo[c][2,7]naphthyridine-5-yl-arylamines-phenol Mannich bases of the amodiaquine-, cycloquine- and pyronaridine-type]. | 2007 Feb |
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| Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed? | 2007 Feb 16 |
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| Rapid dissemination of Plasmodium falciparum drug resistance despite strictly controlled antimalarial use. | 2007 Jan 3 |
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| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of pyronaridine in human urine. | 2007 Jun 15 |
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| Geometric least squares means ratios for the analysis of Plasmodium falciparum in vitro susceptibility to antimalarial drugs. | 2007 Nov 26 |
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| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of pyronaridine in human blood for application to clinical pharmacokinetic studies. | 2007 Sep 21 |
|
| World Antimalarial Resistance Network (WARN) IV: clinical pharmacology. | 2007 Sep 6 |
|
| World Antimalarial Resistance Network (WARN) II: in vitro antimalarial drug susceptibility. | 2007 Sep 6 |
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| The role of anti-malarial drugs in eliminating malaria. | 2008 Dec 11 |
|
| Azithromycin-chloroquine and the intermittent preventive treatment of malaria in pregnancy. | 2008 Dec 16 |
|
| Sulfadoxine-pyrimethamine-based combinations for malaria: a randomised blinded trial to compare efficacy, safety and selection of resistance in Malawi. | 2008 Feb 13 |
|
| Antimalarial therapy selection for quinolone resistance among Escherichia coli in the absence of quinolone exposure, in tropical South America. | 2008 Jul 16 |
|
| No PfATPase6 S769N mutation found in Plasmodium falciparum isolates from China. | 2008 Jul 8 |
|
| Anti-malarial efficacy of pyronaridine and artesunate in combination in vitro and in vivo. | 2008 Mar |
|
| Effect of folate derivatives on the activity of antifolate drugs used against malaria and cancer. | 2008 May |
|
| Plasmodium vivax trophozoites insensitive to chloroquine. | 2008 May 27 |
|
| Fixed-dose pyronaridine-artesunate combination for treatment of uncomplicated falciparum malaria in pediatric patients in Gabon. | 2008 Sep 15 |
|
| Mefloquine--an aminoalcohol with promising antischistosomal properties in mice. | 2009 |
|
| A single LC-tandem mass spectrometry method for the simultaneous determination of 14 antimalarial drugs and their metabolites in human plasma. | 2009 Apr 1 |
|
| In vitro activity of pyronaridine against Plasmodium falciparum and comparative evaluation of anti-malarial drug susceptibility assays. | 2009 Apr 23 |
|
| Residual antimalarials in malaria patients from Tanzania--implications on drug efficacy assessment and spread of parasite resistance. | 2009 Dec 14 |
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| Plasmodium berghei ANKA: selection of resistance to piperaquine and lumefantrine in a mouse model. | 2009 Jul |
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| A comparative, randomized clinical trial of artemisinin/naphtoquine twice daily one day versus artemether/lumefantrine six doses regimen in children and adults with uncomplicated falciparum malaria in Côte d'Ivoire. | 2009 Jul 3 |
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| The efficacy and safety of a new fixed-dose combination of amodiaquine and artesunate in young African children with acute uncomplicated Plasmodium falciparum. | 2009 Mar 16 |
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| Field-adapted sampling of whole blood to determine the levels of amodiaquine and its metabolite in children with uncomplicated malaria treated with amodiaquine plus artesunate combination. | 2009 Mar 30 |
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| 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 |
|
| Synergism between pyronaridine and retinol in Plasmodium falciparum in vitro. | 2009 Oct |
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| Simple field assays to check quality of current artemisinin-based antimalarial combination formulations. | 2009 Sep 30 |
|
| Absorption, distribution, excretion, and pharmacokinetics of 14C-pyronaridine tetraphosphate in male and female Sprague-Dawley rats. | 2010 |
|
| Intermittent preventive treatment in infants for the prevention of malaria in rural Western kenya: a randomized, double-blind placebo-controlled trial. | 2010 Apr 2 |
|
| Sustainable development of a GCP-compliant clinical trials platform in Africa: the malaria clinical trials alliance perspective. | 2010 Apr 20 |
|
| Efficacy and safety of a fixed-dose oral combination of pyronaridine-artesunate compared with artemether-lumefantrine in children and adults with uncomplicated Plasmodium falciparum malaria: a randomised non-inferiority trial. | 2010 Apr 24 |
|
| Pyronaridine-artesunate for uncomplicated falciparum malaria. | 2010 Apr 24 |
|
| Antimalarial drug targets in Plasmodium falciparum predicted by stage-specific metabolic network analysis. | 2010 Aug 31 |
|
| In vitro activity of pyronaridine against multidrug-resistant Plasmodium falciparum and Plasmodium vivax. | 2010 Dec |
|
| In vitro susceptibility of Plasmodium falciparum isolates from Abidjan, Côte d'Ivoire, to artemisinin, chloroquine, dihydroartemisinin and pyronaridine. | 2010 Jan |
|
| [A new antimalarial drug combination]. | 2010 May 5 |
|
| Absence of association between pyronaridine in vitro responses and polymorphisms in genes involved in quinoline resistance in Plasmodium falciparum. | 2010 Nov 25 |
|
| Synergism between pyronaridine and retinol in Plasmodium vivax in vitro. | 2010 Oct |
|
| In vitro activity of antiretroviral drugs against Plasmodium falciparum. | 2011 Nov |
|
| Baseline in vitro activities of the antimalarials pyronaridine and methylene blue against Plasmodium falciparum isolates from Kenya. | 2012 Feb |
|
| Male and female Plasmodium falciparum mature gametocytes show different responses to antimalarial drugs. | 2013 Jul |
Patents
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
677019
Created by
admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
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FDA ORPHAN DRUG |
723819
Created by
admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
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FDA ORPHAN DRUG |
651218
Created by
admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
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| Code System | Code | Type | Description | ||
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156867
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DTXSID00998059
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759834
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2T289F9ACO
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m9387
Created by
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100000115692
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CHEMBL35228
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SUB31202
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76748-86-2
Created by
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ACTIVE MOIETY
SUBSTANCE RECORD
