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MedKoo Cat#: 407844 | Name: Furamidine HCl
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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 HCl
Furamidine HCl
CAS#55368-40-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 407844

Name: Furamidine HCl

CAS#: 55368-40-6 (HCl)

Chemical Formula: C18H18Cl2N4O

Exact Mass: 0.0000

Molecular Weight: 377.27

Elemental Analysis: C, 57.31; H, 4.81; Cl, 18.79; N, 14.85; O, 4.24

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
73819-26-8 (free base) 55368-40-6 (HCl)
Synonym
Furamidine HCl; Furamidine dihydrochloride; DB 75; DB75; DB-75; NSC-305831; NSC305831; NSC 305831; WR199385; WR 199385; WR-199385;
IUPAC/Chemical Name
4,4'-(2,5-furandiyl)bis-benzenecarboximidamide, dihydrochloride
InChi Key
VXNYQUQHOUERTR-UHFFFAOYSA-N
InChi Code
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
SMILES Code
N=C(C1=CC=C(C2=CC=C(C3=CC=C(C(N)=N)C=C3)O2)C=C1)N.[H]Cl.[H]Cl
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
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.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Furamidine dihydrochloride (DB75 dihydrochloride) is a selective protein arginine methyltransferase 1 (PRMT1) inhibitor with an IC50 of 9.4 μM.
In vitro activity:
Furamidine reduced the number of ribonuclear foci per nucleus relative to untreated DM1 myotubes in the 0.25 to 4 μM concentration range tested (Figure 6a). Reference: ACS Chem Biol. 2018 Sep 21;13(9):2708-2718. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6343479/
In vivo activity:
Furamidine was shown to rescue two mis-spliced events in the HSALR DM1 mouse, Atp2a1 and Clcn1, at 20 mg kg−1 daily for 7 days. Reference: ACS Chem Biol. 2018 Sep 21;13(9):2708-2718. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6343479/
Solvent mg/mL mM
Solubility
DMSO 12.1 32.13
DMF 0.5 1.33
Ethanol 1.0 2.65
Water 18.9 49.99
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 377.27 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
Formulation protocol:
1. Jenquin JR, Coonrod LA, Silverglate QA, Pellitier NA, Hale MA, Xia G, Nakamori M, Berglund JA. Furamidine Rescues Myotonic Dystrophy Type I Associated Mis-Splicing through Multiple Mechanisms. ACS Chem Biol. 2018 Sep 21;13(9):2708-2718. doi: 10.1021/acschembio.8b00646. Epub 2018 Aug 27. PMID: 30118588; PMCID: PMC6343479.
In vitro protocol:
1. Jenquin JR, Coonrod LA, Silverglate QA, Pellitier NA, Hale MA, Xia G, Nakamori M, Berglund JA. Furamidine Rescues Myotonic Dystrophy Type I Associated Mis-Splicing through Multiple Mechanisms. ACS Chem Biol. 2018 Sep 21;13(9):2708-2718. doi: 10.1021/acschembio.8b00646. Epub 2018 Aug 27. PMID: 30118588; PMCID: PMC6343479.
In vivo protocol:
1. Jenquin JR, Coonrod LA, Silverglate QA, Pellitier NA, Hale MA, Xia G, Nakamori M, Berglund JA. Furamidine Rescues Myotonic Dystrophy Type I Associated Mis-Splicing through Multiple Mechanisms. ACS Chem Biol. 2018 Sep 21;13(9):2708-2718. doi: 10.1021/acschembio.8b00646. Epub 2018 Aug 27. PMID: 30118588; PMCID: PMC6343479.
1: Sauer B, Skinner-Adams TS, Bouchut A, Chua MJ, Pierrot C, Erdmann F, Robaa D, Schmidt M, Khalife J, Andrews KT, Sippl W. Synthesis, biological characterisation and structure activity relationships of aromatic bisamidines active against Plasmodium falciparum. Eur J Med Chem. 2017 Feb 15;127:22-40. doi: 10.1016/j.ejmech.2016.12.041. Epub 2016 Dec 23. PubMed PMID: 28038325. 2: 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. 3: Siboni RB, Bodner MJ, Khalifa MM, Docter AG, Choi JY, Nakamori M, Haley MM, Berglund JA. Biological Efficacy and Toxicity of Diamidines in Myotonic Dystrophy Type 1 Models. J Med Chem. 2015 Aug 13;58(15):5770-80. doi: 10.1021/acs.jmedchem.5b00356. Epub 2015 Jul 21. PubMed PMID: 26103061; PubMed Central PMCID: PMC4972181. 4: Coles JA, Myburgh E, Ritchie R, Hamilton A, Rodgers J, Mottram JC, Barrett MP, Brewer JM. Intravital imaging of a massive lymphocyte response in the cortical dura of mice after peripheral infection by trypanosomes. PLoS Negl Trop Dis. 2015 Apr 16;9(4):e0003714. doi: 10.1371/journal.pntd.0003714. eCollection 2015 Apr. PubMed PMID: 25881126; PubMed Central PMCID: PMC4400075. 5: 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. 6: Laughlin S, Wang S, Kumar A, Boykin DW, Wilson WD. A novel approach using electrospray ionization mass spectrometry to study competitive binding of small molecules with mixed DNA sequences. Anal Bioanal Chem. 2014 Oct;406(25):6441-5. doi: 10.1007/s00216-014-8044-9. Epub 2014 Jul 30. PubMed PMID: 25074546; PubMed Central PMCID: PMC4339222. 7: Yang S, Wenzler T, Miller PN, Wu H, Boykin DW, Brun R, Wang MZ. Pharmacokinetic comparison to determine the mechanisms underlying the differential efficacies of cationic diamidines against first- and second-stage human African trypanosomiasis. Antimicrob Agents Chemother. 2014 Jul;58(7):4064-74. doi: 10.1128/AAC.02605-14. Epub 2014 May 5. PubMed PMID: 24798280; PubMed Central PMCID: PMC4068519. 8: Yan L, Yan C, Qian K, Su H, Kofsky-Wofford SA, Lee WC, Zhao X, Ho MC, Ivanov I, Zheng YG. Diamidine compounds for selective inhibition of protein arginine methyltransferase 1. J Med Chem. 2014 Mar 27;57(6):2611-22. doi: 10.1021/jm401884z. Epub 2014 Mar 6. PubMed PMID: 24564570; PubMed Central PMCID: PMC3983339. 9: Patrick DA, Bakunov SA, Bakunova SM, Wenzler T, Brun R, Tidwell RR. Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues. Bioorg Med Chem. 2014 Jan 1;22(1):559-76. doi: 10.1016/j.bmc.2013.10.050. Epub 2013 Nov 9. PubMed PMID: 24268543. 10: Munde M, Wang S, Kumar A, Stephens CE, Farahat AA, Boykin DW, Wilson WD, Poon GM. Structure-dependent inhibition of the ETS-family transcription factor PU.1 by novel heterocyclic diamidines. Nucleic Acids Res. 2014 Jan;42(2):1379-90. doi: 10.1093/nar/gkt955. Epub 2013 Oct 23. PubMed PMID: 24157839; PubMed Central PMCID: PMC3902942. 11: Pfeifer ND, Harris KB, Yan GZ, Brouwer KL. Determination of intracellular unbound concentrations and subcellular localization of drugs in rat sandwich-cultured hepatocytes compared with liver tissue. Drug Metab Dispos. 2013 Nov;41(11):1949-56. doi: 10.1124/dmd.113.052134. Epub 2013 Aug 29. PubMed PMID: 23990525; PubMed Central PMCID: PMC3807053. 12: Patrick DA, Bakunov SA, Bakunova SM, Jones SK, Wenzler T, Barszcz T, Kumar A, Boykin DW, Werbovetz KA, Brun R, Tidwell RR. Synthesis and antiprotozoal activities of benzyl phenyl ether diamidine derivatives. Eur J Med Chem. 2013 Sep;67:310-24. doi: 10.1016/j.ejmech.2013.06.033. Epub 2013 Jun 25. PubMed PMID: 23871911. 13: Ning J, Chen W, Li J, Peng Z, Wang J, Ni Z. Structural and energetic insights into sequence-specific interaction in DNA-drug recognition: development of affinity predictor and analysis of binding selectivity. J Mol Model. 2013 Apr;19(4):1573-82. doi: 10.1007/s00894-012-1722-7. Epub 2012 Dec 29. PubMed PMID: 23274531. 14: Sassano MF, Schlesinger AP, Jarstfer MB. Identification of G-Quadruplex Inducers Usinga Simple, Inexpensiveand Rapid High Throughput Assay, and TheirInhibition of Human Telomerase. Open Med Chem J. 2012;6:20-8. doi: 10.2174/1874104501206010020. Epub 2012 Oct 19. PubMed PMID: 23173022; PubMed Central PMCID: PMC3502892. 15: 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. 16: 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. 17: Huang SN, Pommier Y, Marchand C. Tyrosyl-DNA Phosphodiesterase 1 (Tdp1) inhibitors. Expert Opin Ther Pat. 2011 Sep;21(9):1285-92. doi: 10.1517/13543776.2011.604314. Review. PubMed PMID: 21843105; PubMed Central PMCID: PMC3157054. 18: 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. 19: 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. 20: 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.

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