4-({7-chloro-2-methoxybenzo[b]1,5-naphthyridin-10-yl}amino)-2,6-bis(pyrrolidin-1-ylmethyl)phenol; tetrakis(phosphoric acid)

• ChemBase ID: 121845
• Molecular Formular: C29H44ClN5O18P4
• Molecular Mass: 910.030404
• Monoisotopic Mass: 909.13203379
• SMILES: c1(c2nc(ccc2nc2c1ccc(c2)Cl)OC)Nc1cc(c(c(CN2CCCC2)c1)O)CN1CCCC1.P(=O)(O)(O)O.P(=O)(O)(O)O.P(=O)(O)(O)O.P(=O)(O)(O)O
• Canonical SMILES: OP(=O)(O)O.OP(=O)(O)O.OP(=O)(O)O.OP(=O)(O)O.COc1ccc2c(n1)c(Nc1cc(CN3CCCC3)c(c(c1)CN1CCCC1)O)c1c(n2)cc(cc1)Cl
• InChI: 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)
• InChIKey: YKUQEKXHQFYULM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({7-chloro-2-methoxybenzo[b]1,5-naphthyridin-10-yl}amino)-2,6-bis(pyrrolidin-1-ylmethyl)phenol; tetrakis(phosphoric acid)
• IUPAC Traditional name: tetrakis(phosphoric acid); pyronaridine
• Synonyms: 4-((7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-yl)amino)-2,6-bis(pyrrolidin-1-ylmethyl)phenol tetrakis(phosphate); 2-Methoxy-7-chloro-10[3′,5′-bis(pyrrolidinyl-1-methyl-)4′-hydroxyphenyl]aminobenzyl-(b)-1,5-naphthyridine tetraphosphate; Pyronaridine tetraphosphate

Database IDs

• CAS Number: 76748-86-2
• MDL Number: MFCD05863545
• PubChem SID: 162216198
• PubChem CID: 5488630

CALCULATED PROPERTIES

• Acid pKa: 7.969286
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.473129
• LogD (pH = 7.4): 1.9516054
• Log P: 4.1956854
• Molar Refractivity: 147.7446 cm^3
• Polarizability: 59.306362 Å^3
• Polar Surface Area: 73.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: SK4920000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 63-22-41
• Safety Statements: 26-36/37-39
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H318-H361-H413
• GHS Precautionary statements: P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: 4 H3PO4
• Empirical Formula (Hill Notation): C29H32ClN5O2·4H3PO4

DETAILS

Sigma Aldrich - P0049

Biochem/physiol Actions
Pyronaridine blocks β-hematin formation in vitro3 and has inhibitory activity toward P-glycoprotein mediated drug resistance.4 Antimalarial used on conjunction with artensunate.5
Pyronaridine has antimalarial activity. It is antagonistic against naphthoquine and dihydroartemisinin2. Pyronaridine blocks β-hematin formation in vitro3 and has inhibitory activity toward P-glycoprotein mediated drug resistance.4
Application
Pyronaridine, an acridine derivative, is an antimalarial drug. It is used in China as a treatment for drug-resistant falciparum malaria1. It′s in vitro activities have been studies against Plasmodium falciparum in Cameroon2.