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P0049

Sigma-Aldrich

Pyronaridine tetraphosphate

Synonym(s):

2-Methoxy-7-chloro-10[3′,5′-bis(pyrrolidinyl-1-methyl-)4′-hydroxyphenyl]aminobenzyl-(b)-1,5-naphthyridine tetraphosphate

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About This Item

Empirical Formula (Hill Notation):
C29H32ClN5O2·4H3PO4
CAS Number:
76748-86-2
Molecular Weight:
910.03
MDL number:
MFCD05863545
UNSPSC Code:
51101500
PubChem Substance ID:
329819999
NACRES:
NA.85

form

solid

antibiotic activity spectrum

parasites

Mode of action

enzyme | interferes

storage temp.

2-8°C

SMILES string

OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O.COc1ccc2nc3cc(Cl)ccc3c(Nc4cc(CN5CCCC5)c(O)c(CN6CCCC6)c4)c2n1

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)

InChI key

YKUQEKXHQFYULM-UHFFFAOYSA-N

Application

Pyronaridine, an acridine derivative, is used in China as a treatment for drug-resistant falciparum malaria. It′s in vitro activities have been studied against Plasmodium falciparum in Cameroon.

Biochem/physiol Actions

Pyronaridine has antimalarial activity and is used in conjunction with artensunate. It is antagonistic against naphthoquine and dihydroartemisinin. Pyronaridine blocks B-hematin formation in vitro and has inhibitory activity toward P-glycoprotein mediated drug resistance.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Storage class (TRGS 510): Non Combustible Solids

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

P0049-250MG:
P0049-BULK:
P0049-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Matthias Rottmann et al.
Antimicrobial agents and chemotherapy, 64(4) (2020-02-12)
Antimalarial drug resistance in the Plasmodium falciparum parasite poses a constant challenge for drug development. To mitigate this risk, new antimalarial medicines should be developed as fixed-dose combinations. Assessing the pharmacodynamic interactions of potential antimalarial drug combination partners during early
Timothy M E Davis et al.
Antimicrobial agents and chemotherapy, 50(8), 2883-2885 (2006-07-28)
In an in vitro assessment of antimalarial combinations, dihydroartemisinin (DHA) showed no interaction or was mildly antagonistic when combined with piperaquine, pyronaridine, or naphthoquine. Interactions between 4-aminoquinolines and related drugs were also indifferent/antagonistic. The clinical significance of mildly antagonistic DHA
Leonardo K Basco et al.
Antimicrobial agents and chemotherapy, 47(4), 1391-1394 (2003-03-26)
The spread of chloroquine-resistant Plasmodium falciparum calls for a constant search for new drugs. The in vitro activity of piperaquine, a new Chinese synthetic drug belonging to the bisquinolines, was evaluated in 103 fresh clinical isolates of P. falciparum in
Thomas R Lane et al.
Antiviral research, 181, 104863-104863 (2020-07-20)
The recent outbreaks of the Ebola virus (EBOV) in Africa have brought global visibility to the shortage of available therapeutic options to treat patients infected with this or closely related viruses. We have recently computationally identified three molecules which have
Giorgia Mori et al.
Tuberculosis (Edinburgh, Scotland), 112, 98-109 (2018-09-13)
The search for compounds with biological activity for many diseases is turning increasingly to drug repurposing. In this study, we have focused on the European Union-approved antimalarial pyronaridine which was found to have in vitro activity against Mycobacterium tuberculosis (MIC
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