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About This Item
Empirical Formula (Hill Notation):
C25H30N6O2 · 2HCl
CAS Number:
Molecular Weight:
519.47
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32
MDL number:
Product Name
Phe-Arg β-naphthylamide dihydrochloride, cathepsin substrate
Quality Level
assay
≥98% (TLC)
form
powder
solubility
water: 50 mg/mL, clear, colorless to faintly yellow
storage temp.
−20°C
SMILES string
Cl.NC(Cc1ccccc1)C(=O)NC(CCCNC(N)=N)C(=O)Nc2ccc3ccccc3c2
InChI
1S/C25H30N6O2.ClH/c26-21(15-17-7-2-1-3-8-17)23(32)31-22(11-6-14-29-25(27)28)24(33)30-20-13-12-18-9-4-5-10-19(18)16-20;/h1-5,7-10,12-13,16,21-22H,6,11,14-15,26H2,(H,30,33)(H,31,32)(H4,27,28,29);1H
InChI key
ZMTAZQYLEGNUTJ-UHFFFAOYSA-N
General description
Substrate for dipeptidyl aminopeptidase I (cathepsin C).
Phe-Arg β-naphthylamide, a peptidomimetic compound, is an efflux pump inhibitor (EPI). It acts on the major multidrug resistance efflux transporters of Gram-negative bacteria. Phe-Arg -naphthylamide lowers fluoroquinolone resistance in Pseudomonas aeruginosa.
Application
Phe-Arg -naphthylamide dihydrochloride has been used to evaluate the contribution of efflux pumps to antimicrobial resistance. It has also been used for minimal inhibitory concentration testing in the presence of an efflux pump inhibitor.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Commonality among fluoroquinolone-resistant sequence type ST131 extraintestinal Escherichia coli isolates from humans and companion animals in Australia
Platell JL, et al.
Antimicrobial Agents and Chemotherapy, 55(8), 3782-3787 (2011)
Fluoroquinolone resistance mechanisms in multidrug-resistant Escherichia coli isolated from extraintestinal infections in dogs
Gibson JS, et al.
Veterinary Microbiology, 146(1-2), 161-166 (2010)
Proof of an Outer Membrane Target of the Efflux Inhibitor Phe-Arg-beta-Naphthylamide from Random Mutagenesis
Schuster S, et al.
Molecules (Basel), 24(3), 470-470 (2019)