SML1958
BAY 60-6583
≥98% (HPLC)
Synonym(s):
2-[[6-Amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]-2-pyridinyl]thio]-acetamide, BAY 606583, BAY 60–6,583, BAY606583, BR 4887, BR4887
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About This Item
Empirical Formula (Hill Notation):
C19H17N5O2S
CAS Number:
Molecular Weight:
379.44
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
SMILES string
NC1=C(C#N)C(C2=CC=C(OCC3CC3)C=C2)=C(C#N)C(SCC(N)=O)=N1
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)
InChI key
ZTYHZMAZUWOXNC-UHFFFAOYSA-N
Biochem/physiol Actions
BAY 60-6583 is a potent adenosine receptor A2b (A2bR) partial agonist (Ki against 0.3 nM [3H]PSB-603 for binding human/mouse/rat A2bR = 114/136/100 nM) that selectively induces cAMP-dependent transcription activity in CHO transfectants expressing human A2bR (EC50 ~100 nM), but not A1R or A2aR, while exhibiting no affinity toward human/rat/mouse A2aR. BAY 60-6583 also displays low-affinity antagonistic activity toward A1R (Ki against 1 nM [3H]CCPA for binding human/mouse/rat A1R = 387/351/514 nM; IC50 = 7.4 μM against 100 nM CCPA-induced hA1R β-arrestin recruitment) and A3R (Ki against 10 nM [3H]NECA for binding human/mouse/rat A3R = 223/3920/2750 nM; IC50 = 6.7 μM against 30 nM Cl-IB-MECA-induced hA3R β-arrestin recruitment). BAY 60-6583 is widely administered in animals in vivo via i.p. (0.1-80 mg/kg) or i.v. (0.2-2 mg/kg) for studying A2bR-mediated biological responses.
Potent adenosine receptor A2bR partial agonist with low affinity antagonistic activity toward A1R & A3R.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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