55368-40-6

Basic information

• Product Name: 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide
• Synonyms: WR-199385;FuraMidine Dihydrochloride;4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide;2,5-Furandiylbis(1,4-phenylene)bisformamidine;DB75;DB-75;Furamidine;Furamidine (hydrochloride)
• CAS NO: 55368-40-6
• Molecular Formula: C18H16N4O
• Molecular Weight: 0
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 55368-40-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 400-401 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Storage Temp.: -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide(55368-40-6)
• EPA Substance Registry System: 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide(55368-40-6)

Safety Data

• Hazardous Substances Data: 55368-40-6(Hazardous Substances Data)

Usage

Description

4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide, also known as Furamidine dihydrochloride, is a diphenylfuran compound derived from the aromatic drug pentamidine. It is a substrate of the organic cation transporter 1 (OCT1) and is characterized by its yellow solid appearance. 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide has been found to possess antimicrobial, antiparasitic, and antitumor activities, making it a promising candidate for various pharmaceutical applications.

Uses

Used in Antimicrobial Applications:
4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms, making it a potential candidate for treating infections caused by resistant bacteria, fungi, and parasites.
Used in Antiparasitic Applications:
In the field of antiparasitic applications, 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide is used to combat parasitic infections by targeting and disrupting the life cycle of the parasites, thus providing a potential treatment option for various parasitic diseases.
Used in Antitumor Applications:
4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide is used as an antitumor agent for its demonstrated antiproliferative activities against various tumor cell lines. It modulates several oncological signaling pathways, potentially leading to the inhibition of tumor growth and progression.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide is used as a substrate for the development of prodrugs, which are currently being synthesized and tested in clinical trials. These prodrugs aim to enhance the bioavailability and therapeutic outcomes of the compound, making it a valuable asset in the development of new medications.
Used in Drug Delivery Systems:
To improve the delivery and efficacy of 4-[5-(4-carbamimidoylphenyl)-2-furyl]benzenecarboximidamide, various drug delivery systems are being developed. These systems, including organic and metallic nanoparticles, serve as carriers for the compound, aiming to enhance its bioavailability and therapeutic outcomes in targeted applications such as cancer treatment.

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.

in vitro

Furamidine (compound 1; 20 μM; 72 hours; leukemia cell lines) inhibits cell growth for most of the leukemia cell lines except HEL cells which have JAK2V617F mutations.Furamidine (compound 1; 20 μM; 15 hours; 293T cells) treatment significantly reduces the expression level of the methylated GFP-ALY protein in 293T cells.Furamidine binds duplex DNA in the DNA minor groove selectively at AT rich sites [(A/T)4]. Furamidine can also intercalate between GC base pairs of duplex DNA. Furamidine could therefore interfere with DNA processing enzymes such as TDP-1.

in vivo

Furamidine (1 mg/kg; intraperitoneal injection; 3 times a week and repeated every 4 weeks; for 34 weeks; female NZB/NZW mice) and Irinotecan combined treatment suppresses proteinuria and prolongs survival of lupus-prone NZB/NZW mice. The combination treatment does not change the levels of anti-dsDNA antibodies.