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Merck
CN

SML1559

Furamidine dihydrochloride

≥98% (HPLC)

Synonym(s):

2,5-Bis(4-amidinophenyl)furan dihydrochloride, 4,4′-(2,5-Furandiyl)bis-benzenecarboximidamide dihydrochloride, DB 75, DB75, NSC 305831, WR199385

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About This Item

Empirical Formula (Hill Notation):
C18H16N4O · 2HCl
CAS Number:
55368-40-6
Molecular Weight:
377.27
UNSPSC Code:
12352200
NACRES:
NA.77

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Product Name

Furamidine dihydrochloride, ≥98% (HPLC)

SMILES string

[Cl-].[Cl-].N[C+](N)c1ccc(cc1)c2[o]c(cc2)c3ccc(cc3)[C+](N)N

InChI

1S/C18H16N4O.2ClH/c19-17(20)13-5-1-11(2-6-13)15-9-10-16(23-15)12-3-7-14(8-4-12)18(21)22;;/h1-10H,(H3,19,20)(H3,21,22);2*1H

InChI key

VXNYQUQHOUERTR-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 1 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Furamidine (DB75) binds to strings of AT base pair sequences in DNA′s minor groove. Furamidine was originally developed as an anti-parasitic compound for a variety of diseases including Chagas′ disease. Furamidine targets AT rich sequences in trypanosome kinetoplast minicircle DNA (kDNA), resulting in subsequent destruction of the kinetoplast and cell death. Furamidine has also been found to inihbit tyrosyl-DNA phosphodiesterase (Tdp1) and act as a selective protein arginine methyltransferase 1 (PRMT1) inhibitor with an IC50 of 9.4μM.

General description

Furamidine dihydrochloride is an analog of the aromatic drug pentamidine and a substrate of the organic cation transporter 1 (OCT1). A number of prodrugs of furamidine dihydrochloride are being synthesised and are in clinical trial stages.

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000483056
0000483056
0000383628
0000383628
0000261474

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Antiparasitic Compounds That Target DNA
Wilson
Biochimie, 90(7), 999-1014 (2008)
Xin Ming et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(2), 424-430 (2008-10-31)
The antiparasitic activity of aromatic diamidine drugs, pentamidine and furamidine, depends on their entry into the pathogenic protozoa via membrane transporters. However, no such diamidine transporter has been identified in mammalian cells. The goal of this study is to investigate
Yang Liu et al.
The journal of physical chemistry. B, 112(37), 11809-11818 (2008-08-23)
Given the increasing significance of diamidines as DNA-targeted therapeutics and biotechnology reagents, it is important to establish the variations in thermodynamic quantities that characterize the interactions of closely related compounds to different sequence AT binding sites. In this study, an
Leilei Yan et al.
Journal of medicinal chemistry, 57(6), 2611-2622 (2014-02-26)
Protein arginine methylation is a posttranslational modification critical for a variety of biological processes. Misregulation of protein arginine methyltransferases (PRMTs) has been linked to many pathological conditions. Most current PRMT inhibitors display limited specificity and selectivity, indiscriminately targeting many methyltransferase
Smitha Antony et al.
Nucleic acids research, 35(13), 4474-4484 (2007-06-20)
By enzymatically hydrolyzing the terminal phosphodiester bond at the 3'-ends of DNA breaks, tyrosyl-DNA phosphodiesterase (Tdp1) repairs topoisomerase-DNA covalent complexes and processes the DNA ends for DNA repair. To identify novel Tdp1 inhibitors, we developed a high-throughput assay that uses
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