U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=CC=C2N=C3C=C(Cl)C=CC3=C(NC4=CC(CN5CCCC5)=C(O)C(CN6CCCC6)=C4)C2=N1

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

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
266.7 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24590312/
720 mg single, oral
dose: 720 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRONARIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
374 ng × day/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24590312/
720 mg single, oral
dose: 720 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRONARIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.03 day
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24590312/
720 mg single, oral
dose: 720 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRONARIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
OTHER GOV'T
https://www.ema.europa.eu/en/documents/outside-eu-assessment-report/pyramax-public-assessment-report_en.pdf
unknown, unknown
 PYRONARIDINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Male and female Plasmodium falciparum mature gametocytes show different responses to antimalarial drugs.
2013-07
Baseline in vitro activities of the antimalarials pyronaridine and methylene blue against Plasmodium falciparum isolates from Kenya.
2012-02
In vitro activity of antiretroviral drugs against Plasmodium falciparum.
2011-11
Adolescence as risk factor for adverse pregnancy outcome in Central Africa--a cross-sectional study.
2010-12-20
In vitro activity of pyronaridine against multidrug-resistant Plasmodium falciparum and Plasmodium vivax.
2010-12
Absence of association between pyronaridine in vitro responses and polymorphisms in genes involved in quinoline resistance in Plasmodium falciparum.
2010-11-25
Synergism between pyronaridine and retinol in Plasmodium vivax in vitro.
2010-10
Antimalarial drug targets in Plasmodium falciparum predicted by stage-specific metabolic network analysis.
2010-08-31
[A new antimalarial drug combination].
2010-05-05
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.
2010-04-24
Pyronaridine-artesunate for uncomplicated falciparum malaria.
2010-04-24
Sustainable development of a GCP-compliant clinical trials platform in Africa: the malaria clinical trials alliance perspective.
2010-04-20
Intermittent preventive treatment in infants for the prevention of malaria in rural Western kenya: a randomized, double-blind placebo-controlled trial.
2010-04-02
In vitro susceptibility of Plasmodium falciparum isolates from Abidjan, Côte d'Ivoire, to artemisinin, chloroquine, dihydroartemisinin and pyronaridine.
2010-01
Absorption, distribution, excretion, and pharmacokinetics of 14C-pyronaridine tetraphosphate in male and female Sprague-Dawley rats.
2010
Population pharmacokinetics of artesunate and dihydroartemisinin following single- and multiple-dosing of oral artesunate in healthy subjects.
2009-12-18
Residual antimalarials in malaria patients from Tanzania--implications on drug efficacy assessment and spread of parasite resistance.
2009-12-14
Synergism between pyronaridine and retinol in Plasmodium falciparum in vitro.
2009-10
Simple field assays to check quality of current artemisinin-based antimalarial combination formulations.
2009-09-30
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.
2009-07-03
Plasmodium berghei ANKA: selection of resistance to piperaquine and lumefantrine in a mouse model.
2009-07
A systematic review and meta-analysis of evidence for correlation between molecular markers of parasite resistance and treatment outcome in falciparum malaria.
2009-05-04
In vitro activity of pyronaridine against Plasmodium falciparum and comparative evaluation of anti-malarial drug susceptibility assays.
2009-04-23
A single LC-tandem mass spectrometry method for the simultaneous determination of 14 antimalarial drugs and their metabolites in human plasma.
2009-04-01
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.
2009-03-30
The efficacy and safety of a new fixed-dose combination of amodiaquine and artesunate in young African children with acute uncomplicated Plasmodium falciparum.
2009-03-16
Mefloquine--an aminoalcohol with promising antischistosomal properties in mice.
2009
Azithromycin-chloroquine and the intermittent preventive treatment of malaria in pregnancy.
2008-12-16
The role of anti-malarial drugs in eliminating malaria.
2008-12-11
Fixed-dose pyronaridine-artesunate combination for treatment of uncomplicated falciparum malaria in pediatric patients in Gabon.
2008-09-15
Antimalarial therapy selection for quinolone resistance among Escherichia coli in the absence of quinolone exposure, in tropical South America.
2008-07-16
No PfATPase6 S769N mutation found in Plasmodium falciparum isolates from China.
2008-07-08
Plasmodium vivax trophozoites insensitive to chloroquine.
2008-05-27
Effect of folate derivatives on the activity of antifolate drugs used against malaria and cancer.
2008-05
Anti-malarial efficacy of pyronaridine and artesunate in combination in vitro and in vivo.
2008-03
Sulfadoxine-pyrimethamine-based combinations for malaria: a randomised blinded trial to compare efficacy, safety and selection of resistance in Malawi.
2008-02-13
How antimalarial drug resistance affects post-treatment prophylaxis.
2008-01-11
Geometric least squares means ratios for the analysis of Plasmodium falciparum in vitro susceptibility to antimalarial drugs.
2007-11-26
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of pyronaridine in human blood for application to clinical pharmacokinetic studies.
2007-09-21
World Antimalarial Resistance Network (WARN) IV: clinical pharmacology.
2007-09-06
World Antimalarial Resistance Network (WARN) II: in vitro antimalarial drug susceptibility.
2007-09-06
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of pyronaridine in human urine.
2007-06-15
Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed?
2007-02-16
[Benzo[c][2,7]naphthyridine-5-yl-arylamines-phenol Mannich bases of the amodiaquine-, cycloquine- and pyronaridine-type].
2007-02
Overestimating resistance in field testing of malaria parasites: simple methods for estimating high EC50 values using a Bayesian approach.
2007-01-17
Rapid dissemination of Plasmodium falciparum drug resistance despite strictly controlled antimalarial use.
2007-01-03
Potentiation of anti-epileptic drugs effectiveness by pyronaridine in refractory epilepsy.
2007
Activity of azithromycin or erythromycin in combination with antimalarial drugs against multidrug-resistant Plasmodium falciparum in vitro.
2006-12
Treatment of falciparum malaria in the age of drug resistance.
2006-11-15
Antimalarial activity of concanamycin A alone and in combination with pyronaridine.
2006-07
Patents

Patents

JP2006503898A
44
JP2011524365A
34
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:50:41 GMT 2025
Edited
by admin
on Mon Mar 31 20:50:41 GMT 2025
Record UNII
2T289F9ACO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRONARIDINE PHOSPHATE
WHO-DD  
Preferred Name English
PYRONARIDINE TETRAPHOSPHATE
MI  
Common Name English
PYRONARIDINE TETRAPHOSPHATE [MI]
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 Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
FDA ORPHAN DRUG 723819
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
FDA ORPHAN DRUG 651218
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
Code System Code Type Description
PUBCHEM
156867
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID00998059
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
NSC
759834
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
FDA UNII
2T289F9ACO
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
MERCK INDEX
m9387
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY Merck Index
SMS_ID
100000115692
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL35228
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
EVMPD
SUB31202
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
CAS
76748-86-2
Created by admin on Mon Mar 31 20:50:41 GMT 2025 , Edited by admin on Mon Mar 31 20:50:41 GMT 2025
PRIMARY
Related Record Type Details
Structure of PYRONARIDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PYRONARIDINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966