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MedKoo Cat#: 585152 | Name: Binodenoson

Description:

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

Binodenoson, also known as WRC-0470, is a short-acting adenosine A2A receptor agonist.

Chemical Structure

Binodenoson
Binodenoson
CAS#144348-08-3

Theoretical Analysis

MedKoo Cat#: 585152

Name: Binodenoson

CAS#: 144348-08-3

Chemical Formula: C17H25N7O4

Exact Mass: 391.1968

Molecular Weight: 391.43

Elemental Analysis: C, 52.16; H, 6.44; N, 25.05; O, 16.35

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 #
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Synonym
Binodenoson; WRC 0470; WRC-0470; WRC0470; MRE-0470; MRE0470; MRE 0470; SHA-174; SHA174;SHA 174; SHA211; SHA-211; SHA 211;
IUPAC/Chemical Name
2-((Cyclohexylmethylene)hydrazino)adenosine
InChi Key
XJFMHMFFBSOEPR-DNZQAUTHSA-N
InChi Code
InChI=1S/C17H25N7O4/c18-14-11-15(22-17(21-14)23-20-6-9-4-2-1-3-5-9)24(8-19-11)16-13(27)12(26)10(7-25)28-16/h6,8-10,12-13,16,25-27H,1-5,7H2,(H3,18,21,22,23)/b20-6+/t10-,12-,13-,16-/m1/s1
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=C(N/N=C/C4CCCCC4)N=C32)N)O1)O)O
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
>3 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 391.43 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: Glover DK, Ruiz M, Yang JY, Koplan BA, Allen TR, Smith WH, Watson DD, Barrett RJ, Beller GA. Pharmacological stress thallium scintigraphy with 2-cyclohexylmethylidenehydrazinoadenosine (WRC-0470). A novel, short-acting adenosine A2A receptor agonist. Circulation. 1996 Oct 1;94(7):1726-32. PubMed PMID: 8840867. 2: Cerqueira MD. Advances in pharmacologic agents in imaging: new A2A receptor agonists. Curr Cardiol Rep. 2006 Mar;8(2):119-22. Review. PubMed PMID: 16524538. 3: Murray JJ, Weiler JM, Schwartz LB, Busse WW, Katial RK, Lockey RF, McFadden ER Jr, Pixton GC, Barrett RJ. Safety of binodenoson, a selective adenosine A2A receptor agonist vasodilator pharmacological stress agent, in healthy subjects with mild intermittent asthma. Circ Cardiovasc Imaging. 2009 Nov;2(6):492-8. doi: 10.1161/CIRCIMAGING.108.817932. Epub 2009 Sep 17. PubMed PMID: 19920048. 4: Hodgson JM, Dib N, Kern MJ, Bach RG, Barrett RJ. Coronary circulation responses to binodenoson, a selective adenosine A2A receptor agonist. Am J Cardiol. 2007 Jun 1;99(11):1507-12. Epub 2007 Apr 16. PubMed PMID: 17531571. 5: Udelson JE, Heller GV, Wackers FJ, Chai A, Hinchman D, Coleman PS, Dilsizian V, DiCarli M, Hachamovitch R, Johnson JR, Barrett RJ, Gibbons RJ. Randomized, controlled dose-ranging study of the selective adenosine A2A receptor agonist binodenoson for pharmacological stress as an adjunct to myocardial perfusion imaging. Circulation. 2004 Feb 3;109(4):457-64. Epub 2004 Jan 20. PubMed PMID: 14734517. 6: Barrett RJ, Lamson MJ, Johnson J, Smith WB. Pharmacokinetics and safety of binodenoson after intravenous dose escalation in healthy volunteers. J Nucl Cardiol. 2005 Mar-Apr;12(2):166-71. PubMed PMID: 15812370. 7: Zoghbi GJ, Iskandrian AE. Selective adenosine agonists and myocardial perfusion imaging. J Nucl Cardiol. 2012 Feb;19(1):126-41. doi: 10.1007/s12350-011-9474-9. Review. PubMed PMID: 22130964. 8: Hogan CJ, Fang GD, Scheld WM, Linden J, Diduch DR. Inhibiting the inflammatory response in joint sepsis. Arthroscopy. 2001 Mar;17(3):311-315. PubMed PMID: 11239354. 9: Müller CE, Jacobson KA. Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta. 2011 May;1808(5):1290-308. doi: 10.1016/j.bbamem.2010.12.017. Epub 2010 Dec 23. Review. PubMed PMID: 21185259; PubMed Central PMCID: PMC3437328. 10: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 May;26(4):295-318. PubMed PMID: 15319808. 11: Buhr C, Gössl M, Erbel R, Eggebrecht H. Regadenoson in the detection of coronary artery disease. Vasc Health Risk Manag. 2008;4(2):337-40. Review. PubMed PMID: 18561509; PubMed Central PMCID: PMC2496979. 12: Sullivan GW, Linden J, Buster BL, Scheld WM. Neutrophil A2A adenosine receptor inhibits inflammation in a rat model of meningitis: synergy with the type IV phosphodiesterase inhibitor, rolipram. J Infect Dis. 1999 Nov;180(5):1550-60. PubMed PMID: 10515815. 13: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Mar;26(2):129-61. PubMed PMID: 15071612. 14: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Dec;25(10):831-55. PubMed PMID: 14735233. 15: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Sep;29(7):467-509. PubMed PMID: 17982511. 16: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 May;30(4):313-31. PubMed PMID: 18773127. 17: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Apr;30(3):231-51. PubMed PMID: 18597009. 18: Iskandrian AE. A new generation of coronary vasodilators in stress perfusion imaging. Am J Cardiol. 2007 Jun 1;99(11):1619-20. Epub 2007 Apr 18. PubMed PMID: 17531594. 19: Mitka M. New stress test agents reduce adverse effects. JAMA. 2008 May 14;299(18):2140. doi: 10.1001/jama.299.18.2140. PubMed PMID: 18477777. 20: Gao Z, Li Z, Baker SP, Lasley RD, Meyer S, Elzein E, Palle V, Zablocki JA, Blackburn B, Belardinelli L. Novel short-acting A2A adenosine receptor agonists for coronary vasodilation: inverse relationship between affinity and duration of action of A2A agonists. J Pharmacol Exp Ther. 2001 Jul;298(1):209-18. PubMed PMID: 11408544.