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MedKoo Cat#: 581254 | Name: Furamidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Furamidine, also known as DB75, is a cell-permeable inhibitor of protein arginine methyltransferase 1 (PRMT1) that is selective for PRMT1. 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 the enzyme active site and is primarily competitive with the substrate and noncompetitive toward the cofactor. Furthermore, cellular studies revealed that 1 is cell membrane permeable and effectively inhibits intracellular PRMT1 activity and blocks cell proliferation in leukemia cell lines with different genetic lesions.

Chemical Structure

Furamidine
Furamidine
CAS#73819-26-8 (free base)

Theoretical Analysis

MedKoo Cat#: 581254

Name: Furamidine

CAS#: 73819-26-8 (free base)

Chemical Formula: C18H16N4O

Exact Mass: 304.1324

Molecular Weight: 304.35

Elemental Analysis: C, 71.04; H, 5.30; N, 18.41; O, 5.26

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
73819-26-8 (free base) 55368-40-6 (HCl)
Synonym
Furamidine; Furandiamidine; DB 75; DB75; DB-75; NSC-305831; NSC305831; NSC 305831;
IUPAC/Chemical Name
Benzenecarboximidamide, 4,4'-(2,5-furandiyl)bis-
InChi Key
ZJHZBDRZEZEDGB-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16N4O/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)
SMILES Code
N=C(C1=CC=C(C2=CC=C(C3=CC=C(C(N)=N)C=C3)O2)C=C1)N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 304.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Keil A, Frese-Schaper M, Steiner SK, Körner M, Schmid RA, Frese S. The Topoisomerase I Inhibitor Irinotecan and the Tyrosyl-DNA Phosphodiesterase 1 Inhibitor Furamidine Synergistically Suppress Murine Lupus Nephritis. Arthritis Rheumatol. 2015 Jul;67(7):1858-67. doi: 10.1002/art.39119. PubMed PMID: 25779651. 2: Farahat AA, Paliakov E, Kumar A, Barghash AE, Goda FE, Eisa HM, Wenzler T, Brun R, Liu Y, Wilson WD, Boykin DW. Exploration of larger central ring linkers in furamidine analogues: synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties. Bioorg Med Chem. 2011 Apr 1;19(7):2156-67. doi: 10.1016/j.bmc.2011.02.045. Epub 2011 Mar 1. PubMed PMID: 21421317. 3: Ming X, Ju W, Wu H, Tidwell RR, Hall JE, Thakker DR. Transport of dicationic drugs pentamidine and furamidine by human organic cation transporters. Drug Metab Dispos. 2009 Feb;37(2):424-30. doi: 10.1124/dmd.108.024083. Epub 2008 Oct 29. PubMed PMID: 18971316. 4: Ward CP, Wong PE, Burchmore RJ, de Koning HP, Barrett MP. Trypanocidal furamidine analogues: influence of pyridine nitrogens on trypanocidal activity, transport kinetics, and resistance patterns. Antimicrob Agents Chemother. 2011 May;55(5):2352-61. doi: 10.1128/AAC.01551-10. Epub 2011 Mar 14. PubMed PMID: 21402852; PubMed Central PMCID: PMC3088251. 5: Berger O, Kaniti A, van Ba CT, Vial H, Ward SA, Biagini GA, Bray PG, O'Neill PM. Synthesis and antimalarial activities of a diverse set of triazole-containing furamidine analogues. ChemMedChem. 2011 Nov 4;6(11):2094-108. doi: 10.1002/cmdc.201100265. Epub 2011 Sep 8. PubMed PMID: 21905228. 6: Antony S, Marchand C, Stephen AG, Thibaut L, Agama KK, Fisher RJ, Pommier Y. Novel high-throughput electrochemiluminescent assay for identification of human tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors and characterization of furamidine (NSC 305831) as an inhibitor of Tdp1. Nucleic Acids Res. 2007;35(13):4474-84. Epub 2007 Jun 18. PubMed PMID: 17576665; PubMed Central PMCID: PMC1935015. 7: Lansiaux A, Dassonneville L, Facompré M, Kumar A, Stephens CE, Bajic M, Tanious F, Wilson WD, Boykin DW, Bailly C. Distribution of furamidine analogues in tumor cells: influence of the number of positive charges. J Med Chem. 2002 May 9;45(10):1994-2002. PubMed PMID: 11985467. 8: Ismail MA, Brun R, Easterbrook JD, Tanious FA, Wilson WD, Boykin DW. Synthesis and antiprotozoal activity of aza-analogues of furamidine. J Med Chem. 2003 Oct 23;46(22):4761-9. PubMed PMID: 14561095. 9: Ansede JH, Anbazhagan M, Brun R, Easterbrook JD, Hall JE, Boykin DW. O-alkoxyamidine prodrugs of furamidine: in vitro transport and microsomal metabolism as indicators of in vivo efficacy in a mouse model of Trypanosoma brucei rhodesiense infection. J Med Chem. 2004 Aug 12;47(17):4335-8. PubMed PMID: 15294005. 10: Yan GZ, Brouwer KL, Pollack GM, Wang MZ, Tidwell RR, Hall JE, Paine MF. Mechanisms underlying differences in systemic exposure of structurally similar active metabolites: comparison of two preclinical hepatic models. J Pharmacol Exp Ther. 2011 May;337(2):503-12. doi: 10.1124/jpet.110.177220. Epub 2011 Feb 14. PubMed PMID: 21320872; PubMed Central PMCID: PMC3083101. 11: De Souza EM, Lansiaux A, Bailly C, Wilson WD, Hu Q, Boykin DW, Batista MM, Araújo-Jorge TC, Soeiro MN. Phenyl substitution of furamidine markedly potentiates its anti-parasitic activity against Trypanosoma cruzi and Leishmania amazonensis. Biochem Pharmacol. 2004 Aug 15;68(4):593-600. PubMed PMID: 15276066. 12: de Souza EM, Oliveira GM, Boykin DW, Kumar A, Hu Q, De Nazaré C Soeiro M. Trypanocidal activity of the phenyl-substituted analogue of furamidine DB569 against Trypanosoma cruzi infection in vivo. J Antimicrob Chemother. 2006 Sep;58(3):610-4. Epub 2006 Jul 19. PubMed PMID: 16854954. 13: Saulter JY, Kurian JR, Trepanier LA, Tidwell RR, Bridges AS, Boykin DW, Stephens CE, Anbazhagan M, Hall JE. Unusual dehydroxylation of antimicrobial amidoxime prodrugs by cytochrome b5 and NADH cytochrome b5 reductase. Drug Metab Dispos. 2005 Dec;33(12):1886-93. Epub 2005 Aug 30. PubMed PMID: 16131524. 14: Lansiaux A, Tanious F, Mishal Z, Dassonneville L, Kumar A, Stephens CE, Hu Q, Wilson WD, Boykin DW, Bailly C. Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution. Cancer Res. 2002 Dec 15;62(24):7219-29. PubMed PMID: 12499262. 15: Nguyen B, Tardy C, Bailly C, Colson P, Houssier C, Kumar A, Boykin DW, Wilson WD. Influence of compound structure on affinity, sequence selectivity, and mode of binding to DNA for unfused aromatic dications related to furamidine. Biopolymers. 2002 Apr 15;63(5):281-97. PubMed PMID: 11877739. 16: ROBEV S, TODOROV S. [A study of the effect of N-phenyl-benzamidine, N-phenyl-2-furamidine and N-phenylamide of thiophene-2-carboxylic acid on the radioresistance of suspensions of B. anthracis, B. cereus, Candida albicans and Staphyl. aureus following their irradiation with gamma rays]. Suvr Med (Sofiia). 1960;11(6):56-61. Bulgarian. PubMed PMID: 13742233. 17: de Souza EM, Oliveira GM, Soeiro Mde N. Electrocardiographic findings in acutely and chronically T. cruzi-infected mice treated by a phenyl-substituted analogue of furamidine DB569. Drug Target Insights. 2007;2:61-9. Epub 2007 Mar 5. PubMed PMID: 21901063; PubMed Central PMCID: PMC3155222. 18: Laughton CA, Tanious F, Nunn CM, Boykin DW, Wilson WD, Neidle S. A crystallographic and spectroscopic study of the complex between d(CGCGAATTCGCG)2 and 2,5-bis(4-guanylphenyl)furan, an analogue of berenil. Structural origins of enhanced DNA-binding affinity. Biochemistry. 1996 May 7;35(18):5655-61. PubMed PMID: 8639524. 19: Yan GZ, Generaux CN, Yoon M, Goldsmith RB, Tidwell RR, Hall JE, Olson CA, Clewell HJ, Brouwer KL, Paine MF. A semiphysiologically based pharmacokinetic modeling approach to predict the dose-exposure relationship of an antiparasitic prodrug/active metabolite pair. Drug Metab Dispos. 2012 Jan;40(1):6-17. doi: 10.1124/dmd.111.040063. Epub 2011 Sep 27. PubMed PMID: 21953913; PubMed Central PMCID: PMC3250045. 20: Yang G, Choi G, No JH. Antileishmanial Mechanism of Diamidines Involves Targeting Kinetoplasts. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6828-6836. doi: 10.1128/AAC.01129-16. Print 2016 Nov. PubMed PMID: 27600039; PubMed Central PMCID: PMC5075092.