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MedKoo Cat#: 532345 | Name: NF449
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Description:

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

NF449 is a potent purinergic receptor antagonist that displays high selectivity for P2X1 (IC50 values are 0.28, 0.69, 120, 1820, 47000 and > 300000 nM for rP2X1, rP2X1+5, rP2X2+3, rP2X3, rP2X2 and P2X4 receptors respectively). NF449 provides antithrombotic protection in vivo. NF449 also acts as a Gsα-selective antagonist.

Chemical Structure

NF449
CAS#627034-85-9

Theoretical Analysis

MedKoo Cat#: 532345

Name: NF449

CAS#: 627034-85-9

Chemical Formula: C41H24N6Na8O29S8

Exact Mass: 1503.7535

Molecular Weight: 1505.05

Elemental Analysis: C, 32.72; H, 1.61; N, 5.58; Na, 12.22; O, 30.83; S, 17.04

Price and Availability

Size Price Availability Quantity
5mg USD 220.00
10mg USD 380.00
50mg USD 1,030.00
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Related CAS #
No Data
Synonym
NF449; NF 449; NF-449.
IUPAC/Chemical Name
4,4',4'',4'''-[Carbonylbis(imino-5,1,3-benzenetriyl-bis(carbonylimino))]tetrakis-1,3-benzenedisulfonic acid, octasodium salt
InChi Key
KCBZSNWCUJBMHF-UHFFFAOYSA-F
InChi Code
InChI=1S/C41H32N6O29S8.8Na/c48-37(44-29-5-1-25(77(53,54)55)15-33(29)81(65,66)67)19-9-20(38(49)45-30-6-2-26(78(56,57)58)16-34(30)82(68,69)70)12-23(11-19)42-41(52)43-24-13-21(39(50)46-31-7-3-27(79(59,60)61)17-35(31)83(71,72)73)10-22(14-24)40(51)47-32-8-4-28(80(62,63)64)18-36(32)84(74,75)76;;;;;;;;/h1-18H,(H,44,48)(H,45,49)(H,46,50)(H,47,51)(H2,42,43,52)(H,53,54,55)(H,56,57,58)(H,59,60,61)(H,62,63,64)(H,65,66,67)(H,68,69,70)(H,71,72,73)(H,74,75,76);;;;;;;;/q;8*+1/p-8
SMILES Code
O=C(NC1=CC(C(NC2=CC=C(S(=O)([O-])=O)C=C2S(=O)([O-])=O)=O)=CC(C(NC3=CC=C(S(=O)([O-])=O)C=C3S(=O)([O-])=O)=O)=C1)NC4=CC(C(NC5=CC=C(S(=O)([O-])=O)C=C5S(=O)([O-])=O)=O)=CC(C(NC6=CC=C(S(=O)([O-])=O)C=C6S(=O)([O-])=O)=O)=C4.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
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 1,505.05 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: Nishimura Y, McLaughlin NP, Pan J, Goldstein S, Hafenstein S, Shimizu H, Winkler JD, Bergelson JM. The Suramin Derivative NF449 Interacts with the 5-fold Vertex of the Enterovirus A71 Capsid to Prevent Virus Attachment to PSGL-1 and Heparan Sulfate. PLoS Pathog. 2015 Oct 2;11(10):e1005184. doi: 10.1371/journal.ppat.1005184. eCollection 2015 Oct 2. PubMed PMID: 26430888; PubMed Central PMCID: PMC4592248. 2: Farmer LK, Schmid R, Evans RJ. Use of chimeras, point mutants, and molecular modeling to map the antagonist-binding site of 4,4',4″,4‴-(carbonylbis-(imino-5,1,3-benzenetriylbis(carbonylimino)))tetrakisbenz ene-1,3-disulfonic acid (NF449) at P2X1 receptors for ATP. J Biol Chem. 2015 Jan 16;290(3):1559-69. doi: 10.1074/jbc.M114.592246. Epub 2014 Nov 25. PubMed PMID: 25425641; PubMed Central PMCID: PMC4340402. 3: El-Ajouz S, Ray D, Allsopp RC, Evans RJ. Molecular basis of selective antagonism of the P2X1 receptor for ATP by NF449 and suramin: contribution of basic amino acids in the cysteine-rich loop. Br J Pharmacol. 2012 Jan;165(2):390-400. doi: 10.1111/j.1476-5381.2011.01534.x. PubMed PMID: 21671897; PubMed Central PMCID: PMC3268193. 4: Su TR, Hung YS, Huang SS, Su HH, Su CC, Hsiao G, Chen YH, Lin MJ. Study of the reversal effect of NF449 on neuromuscular blockade induced by d-tubocurarine. Life Sci. 2011 Jun 6;88(23-24):1039-46. doi: 10.1016/j.lfs.2011.03.013. Epub 2011 Mar 28. PubMed PMID: 21453711. 5: Krejci P, Murakami S, Prochazkova J, Trantirek L, Chlebova K, Ouyang Z, Aklian A, Smutny J, Bryja V, Kozubik A, Wilcox WR. NF449 is a novel inhibitor of fibroblast growth factor receptor 3 (FGFR3) signaling active in chondrocytes and multiple myeloma cells. J Biol Chem. 2010 Jul 2;285(27):20644-53. doi: 10.1074/jbc.M109.083626. Epub 2010 May 3. PubMed PMID: 20439987; PubMed Central PMCID: PMC2898326. 6: Hechler B, Magnenat S, Zighetti ML, Kassack MU, Ullmann H, Cazenave JP, Evans R, Cattaneo M, Gachet C. Inhibition of platelet functions and thrombosis through selective or nonselective inhibition of the platelet P2 receptors with increasing doses of NF449 [4,4',4'',4'''-(carbonylbis(imino-5,1,3-benzenetriylbis-(carbonylimino)))tetrakis -benzene-1,3-disulfonic acid octasodium salt]. J Pharmacol Exp Ther. 2005 Jul;314(1):232-43. Epub 2005 Mar 25. PubMed PMID: 15792995. 7: Rettinger J, Braun K, Hochmann H, Kassack MU, Ullmann H, Nickel P, Schmalzing G, Lambrecht G. Profiling at recombinant homomeric and heteromeric rat P2X receptors identifies the suramin analogue NF449 as a highly potent P2X1 receptor antagonist. Neuropharmacology. 2005 Mar;48(3):461-8. PubMed PMID: 15721178. 8: Kassack MU, Braun K, Ganso M, Ullmann H, Nickel P, Böing B, Müller G, Lambrecht G. Structure-activity relationships of analogues of NF449 confirm NF449 as the most potent and selective known P2X1 receptor antagonist. Eur J Med Chem. 2004 Apr;39(4):345-57. PubMed PMID: 15072843. 9: Hülsmann M, Nickel P, Kassack M, Schmalzing G, Lambrecht G, Markwardt F. NF449, a novel picomolar potency antagonist at human P2X1 receptors. Eur J Pharmacol. 2003 May 30;470(1-2):1-7. PubMed PMID: 12787824. 10: Braun K, Rettinger J, Ganso M, Kassack M, Hildebrandt C, Ullmann H, Nickel P, Schmalzing G, Lambrecht G. NF449: a subnanomolar potency antagonist at recombinant rat P2X1 receptors. Naunyn Schmiedebergs Arch Pharmacol. 2001 Sep;364(3):285-90. PubMed PMID: 11521173.