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Details

Stereochemistry ACHIRAL
Molecular Formula C29H32ClN5O2
Molecular Weight 518.05
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRONARIDINE

SMILES

COC1=CC=C2N=C3C=C(Cl)C=CC3=C(NC4=CC(CN5CCCC5)=C(O)C(CN6CCCC6)=C4)C2=N1

InChI

InChIKey=DJUFPMUQJKWIJB-UHFFFAOYSA-N
InChI=1S/C29H32ClN5O2/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/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32)

HIDE SMILES / InChI
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
[In vitro response of Plasmodium falciparum FCC1/HN to artesunate, pyronaridine and other antimalarials].
2002
Function and mechanism of pyronaridine: a new inhibitor of P-glycoprotein-mediated multidrug resistance.
2002 Jun
New antimalarial drugs.
2003 Nov 10
Liquid chromatographic determination of pyronaridine in human plasma and oral dosage form.
2003 Oct 5
[[1]Benzothieno[3,2-b]pyridin-4-yl-amine--synthesis and investigation of activity against malaria].
2004 Jul
[[1]Benzofuro[3,2-b]pyridin-4-yl-amines - synthesis and investigation of activity against malaria].
2004 Jun
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.
2005 Oct 4
Antimalarial activity of concanamycin A alone and in combination with pyronaridine.
2006 Jul
In vitro activity of pyronaridine against Plasmodium falciparum and comparative evaluation of anti-malarial drug susceptibility assays.
2009 Apr 23
Population pharmacokinetics of artesunate and dihydroartemisinin following single- and multiple-dosing of oral artesunate in healthy subjects.
2009 Dec 18
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
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

Patents

JP2006503898A
44
JP2011524365A
34
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:27:27 GMT 2025
Edited
by admin
on Mon Mar 31 18:27:27 GMT 2025
Record UNII
TD3P7Q3SG6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALARIDINE
Preferred Name English
PYRONARIDINE
INN   MI   WHO-DD  
INN  
Official Name English
4-((7-CHLORO-2-METHOXYBENZO(B)-1,5-NAPHTHYRIDIN-10-YL)AMINO)-2,6-BIS(1-PYRROLIDINYLMETHYL)PHENOL
Systematic Name English
pyronaridine [INN]
Common Name English
4-((7-CHLORO-2-METHOXYBENZO(B)(1,5)NAPHTHYRIDIN-10-YL)AMINO)-2,6-BIS((PYRROLIDIN-1-YL)METHYL)PHENOL
Systematic Name English
PYRONARIDINE [MI]
Common Name English
Pyronaridine [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 696919
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
FDA ORPHAN DRUG 719219
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
NCI_THESAURUS C271
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
WHO-ATC P01BF06
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
Code System Code Type Description
WIKIPEDIA
PYRONARIDINE
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID60996354
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
CAS
74847-35-1
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
PUBCHEM
107771
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
DRUG CENTRAL
4339
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
NCI_THESAURUS
C90737
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
EVMPD
SUB31201
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
INN
8833
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
DRUG BANK
DB12975
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
FDA UNII
TD3P7Q3SG6
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
MERCK INDEX
m9387
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY Merck Index
MESH
C027871
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
SMS_ID
100000115691
Created by admin on Mon Mar 31 18:27:27 GMT 2025 , Edited by admin on Mon Mar 31 18:27:27 GMT 2025
PRIMARY
Related Record Type Details
Structure of PYRONARIDINE TETRAPHOSPHATE
SALT/SOLVATE -> PARENT
Plasmodium falciparum
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of PYRONARIDINE
ACTIVE MOIETY
NIH
NCATS
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