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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=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
Plasmodium falciparum: in vitro interactions of artemisinin with amodiaquine, pyronaridine, and chloroquine.
2002 Jan
Function and mechanism of pyronaridine: a new inhibitor of P-glycoprotein-mediated multidrug resistance.
2002 Jun
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
World Antimalarial Resistance Network (WARN) IV: clinical pharmacology.
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
How antimalarial drug resistance affects post-treatment prophylaxis.
2008 Jan 11
No PfATPase6 S769N mutation found in Plasmodium falciparum isolates from China.
2008 Jul 8
Plasmodium vivax trophozoites insensitive to chloroquine.
2008 May 27
Synergism between pyronaridine and retinol in Plasmodium vivax in vitro.
2010 Oct
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 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
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