BAY 60–6583

BAY 60–6583
Names
	IUPAC name 2-[6-amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]pyridin-2-ylsulfanyl]acetamide
	Other names BAY 60–6583
Identifiers
CAS Number	910487-58-0;
3D model (JSmol)	Interactive image;
ChemSpider	9892551;
IUPHAR/BPS	3289;
PubChem CID	11717831;
	InChI InChI=1S/C19H17N5O2S/c20-7-14-17(12-3-5-13(6-4-12)26-9-11-1-2-11)15(8-21)19(24-18(14)23)27-10-16(22)25/h3-6,11H,1-2,9-10H2,(H2,22,25)(H2,23,24) Key: ZTYHZMAZUWOXNC-UHFFFAOYSA-N; InChI=1/C19H17N5O2S/c20-7-14-17(12-3-5-13(6-4-12)26-9-11-1-2-11)15(8-21)19(24-18(14)23)27-10-16(22)25/h3-6,11H,1-2,9-10H2,(H2,22,25)(H2,23,24) Key: ZTYHZMAZUWOXNC-UHFFFAOYAY;
	SMILES N#Cc1c(SCC(N)=O)nc(N)c(C#N)c1-c3ccc(cc3)OCC2CC2;
Properties
Chemical formula	C19H17N5O2S
Molar mass	379.435
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

BAY 60–6583 is a selective adenosine A_2B receptor agonist.[1] It has been shown to provide protection from ischemia (lack of oxygen due to blocked blood supply) in both the heart and kidney of test animals,[2][3] and has also been shown to be beneficial in treatment of acute lung and brain injury,[4][5], as well as claimed anti-aging and anti-obesity effects,[6] showing a range of potential applications for selective A_2B agonists.

References

Baraldi PG, Tabrizi MA, Fruttarolo F, Romagnoli R, Preti D. Recent improvements in the development of A(2B) adenosine receptor agonists. Purinergic Signalling. 2008 Dec;4(4):287-303. PMID 18443746
Eckle T, Krahn T, Grenz A, Köhler D, Mittelbronn M, Ledent C, Jacobson MA, Osswald H, Thompson LF, Unertl K, Eltzschig HK. Cardioprotection by ecto-5'-nucleotidase (CD73) and A2B adenosine receptors. Circulation. 2007 Mar 27;115(12):1581-90. PMID 17353435
Grenz A, Osswald H, Eckle T, Yang D, Zhang H, Tran ZV, Klingel K, Ravid K, Eltzschig HK. The reno-vascular A2B adenosine receptor protects the kidney from ischemia. PLoS Medicine. 2008 Jun 24;5(6):e137. PMID 18578565
Eckle T, Grenz A, Laucher S, Eltzschig HK. A2B adenosine receptor signaling attenuates acute lung injury by enhancing alveolar fluid clearance in mice. Journal of Clinical Investigation. 2008 Oct;118(10):3301-15. PMID 18787641
Li Q, Han X, Lan X, Hong X, Li Q, Gao Y, Luo T, Yang Q, Koehler RC, Zhai Y, Zhou J, Wang J. Inhibition of tPA-induced hemorrhagic transformation involves adenosine A2b receptor activation after cerebral ischemia. Neurobiology of Disease. 2017 Aug; 108: 173-182. PMID 28830843 doi: 10.1016/j.nbd.2017.08.011
Gnad T, Navarro G, Lahesmaa M, et al. Adenosine/A2B Receptor Signaling Ameliorates the Effects of Aging and Counteracts Obesity. Cell Metab. 2020;32(1):56-70.e7. doi:10.1016/j.cmet.2020.06.006

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[1] Baraldi PG, Tabrizi MA, Fruttarolo F, Romagnoli R, Preti D. Recent improvements in the development of A(2B) adenosine receptor agonists. Purinergic Signalling. 2008 Dec;4(4):287-303. PMID 18443746

[2] Eckle T, Krahn T, Grenz A, Köhler D, Mittelbronn M, Ledent C, Jacobson MA, Osswald H, Thompson LF, Unertl K, Eltzschig HK. Cardioprotection by ecto-5'-nucleotidase (CD73) and A2B adenosine receptors. Circulation. 2007 Mar 27;115(12):1581-90. PMID 17353435

[3] Grenz A, Osswald H, Eckle T, Yang D, Zhang H, Tran ZV, Klingel K, Ravid K, Eltzschig HK. The reno-vascular A2B adenosine receptor protects the kidney from ischemia. PLoS Medicine. 2008 Jun 24;5(6):e137. PMID 18578565

[4] Eckle T, Grenz A, Laucher S, Eltzschig HK. A2B adenosine receptor signaling attenuates acute lung injury by enhancing alveolar fluid clearance in mice. Journal of Clinical Investigation. 2008 Oct;118(10):3301-15. PMID 18787641

[5] Li Q, Han X, Lan X, Hong X, Li Q, Gao Y, Luo T, Yang Q, Koehler RC, Zhai Y, Zhou J, Wang J. Inhibition of tPA-induced hemorrhagic transformation involves adenosine A2b receptor activation after cerebral ischemia. Neurobiology of Disease. 2017 Aug; 108: 173-182. PMID 28830843 doi: 10.1016/j.nbd.2017.08.011

[6] Gnad T, Navarro G, Lahesmaa M, et al. Adenosine/A2B Receptor Signaling Ameliorates the Effects of Aging and Counteracts Obesity. Cell Metab. 2020;32(1):56-70.e7. doi:10.1016/j.cmet.2020.06.006