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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
Structure of PYRONARIDINE TETRAPHOSPHATE

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)

HIDE SMILES / InChI

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 C29H32ClN5O2
Molecular Weight 518.05
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Activity of azithromycin or erythromycin in combination with antimalarial drugs against multidrug-resistant Plasmodium falciparum in vitro.
2006 Dec
Antimalarial activity of concanamycin A alone and in combination with pyronaridine.
2006 Jul
Treatment of falciparum malaria in the age of drug resistance.
2006 Oct-Dec
Potentiation of anti-epileptic drugs effectiveness by pyronaridine in refractory epilepsy.
2007
[Benzo[c][2,7]naphthyridine-5-yl-arylamines-phenol Mannich bases of the amodiaquine-, cycloquine- and pyronaridine-type].
2007 Feb
Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed?
2007 Feb 16
Overestimating resistance in field testing of malaria parasites: simple methods for estimating high EC50 values using a Bayesian approach.
2007 Jan 17
Rapid dissemination of Plasmodium falciparum drug resistance despite strictly controlled antimalarial use.
2007 Jan 3
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of pyronaridine in human urine.
2007 Jun 15
Geometric least squares means ratios for the analysis of Plasmodium falciparum in vitro susceptibility to antimalarial drugs.
2007 Nov 26
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
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
How antimalarial drug resistance affects post-treatment prophylaxis.
2008 Jan 11
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
Population pharmacokinetics of artesunate and dihydroartemisinin following single- and multiple-dosing of oral artesunate in healthy subjects.
2009 Dec 18
Plasmodium berghei ANKA: selection of resistance to piperaquine and lumefantrine in a mouse model.
2009 Jul
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
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
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
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
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
Adolescence as risk factor for adverse pregnancy outcome in Central Africa--a cross-sectional study.
2010 Dec 20
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:26:56 GMT 2023
Edited
by admin
on Sat Dec 16 01:26:56 GMT 2023
Record UNII
2T289F9ACO
Record Status Validated (UNII)
Record Version
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Name Type Language
PYRONARIDINE TETRAPHOSPHATE
MI  
Common Name English
PYRONARIDINE TETRAPHOSPHATE [MI]
Common Name English
PYRONARIDINE PHOSPHATE
WHO-DD  
Common Name English
PHENOL, 4-((7-CHLORO-2-METHOXYBENZO(B)-1,5-NAPHTHYRIDIN-10-YL)AMINO)-2,6-BIS(1-PYRROLIDINYLMETHYL)-, PHOSPHATE (1:4) (SALT)
Common Name English
Pyronaridine phosphate [WHO-DD]
Common Name English
NSC-759834
Code English
PHENOL, 4-((7-CHLORO-2-METHOXYBENZO(B)-1,5-NAPHTHYRIDIN-10-YL)AMINO)-2,6-BIS(1-PYRROLIDINYLMETHYL)-, PHOSPHATE (1:4)
Common Name English
Classification Tree Code System Code
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
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
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
Code System Code Type Description
PUBCHEM
156867
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID00998059
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
NSC
759834
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
FDA UNII
2T289F9ACO
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
MERCK INDEX
m9387
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY Merck Index
SMS_ID
100000115692
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL35228
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
EVMPD
SUB31202
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
CAS
76748-86-2
Created by admin on Sat Dec 16 01:26:56 GMT 2023 , Edited by admin on Sat Dec 16 01:26:56 GMT 2023
PRIMARY
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