GP531 is a potent second-generation adenosine modulator that is pharmacologically silenced under basal conditions but increases local endogenous adenosine during ischemia.

Physicochemical Properties

Molecular Formula	C16H21N5O4
Molecular Weight	347.369043111801
Exact Mass	347.159
CAS #	142344-87-4
PubChem CID	164444
Appearance	Typically exists as solid at room temperature
Density	1.6g/cm3
Boiling Point	703.1ºC at 760mmHg
Flash Point	379ºC
Vapour Pressure	9.55E-21mmHg at 25°C
Index of Refraction	1.729
LogP	0.829
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Heavy Atom Count	25
Complexity	462
Defined Atom Stereocenter Count	4
SMILES	O1[C@H]([C@@H]([C@@H]([C@H]1CNCC1C=CC=CC=1)O)O)N1C=NC(C(N)=O)=C1N
InChi Key	LECUGLHMNZTZQB-XNIJJKJLSA-N
InChi Code	InChI=1S/C16H21N5O4/c17-14-11(15(18)24)20-8-21(14)16-13(23)12(22)10(25-16)7-19-6-9-4-2-1-3-5-9/h1-5,8,10,12-13,16,19,22-23H,6-7,17H2,(H2,18,24)/t10-,12-,13-,16-/m1/s1
Chemical Name	5-amino-1-[(2R,3R,4S,5R)-5-[(benzylamino)methyl]-3,4-dihydroxyoxolan-2-yl]imidazole-4-carboxamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vivo

In comparison to vehicle, low-dose GP531 decreased the extent of the anatomic no-reflow zone by 31% and the size of the infarct by 34%. The no-reflow area and infarct size were lowered by 16% and 22%, respectively, at high dosages. Blood flow or hemodynamics are unaffected by GP531. Even at lesser dosages, GP531 is useful in lessening the severity of ischemia/reperfusion injury without producing the negative hemodynamic consequences of adenosine treatment, such as bradycardia and hypotension [1]. Heart rate and mean aortic pressure were unaffected by GP531 infusion, but end-diastolic pressure, end-diastolic volume, end-systolic volume, and end-diastolic wall stress in the left ventricle were all markedly decreased. Without raising MVO2, GP531 dramatically raises end-systolic PVR slope, left ventricular EF, and the deceleration duration of early mitral inflow velocity [2].

References

[1]. Hale SL, et al. Cardioprotection with adenosine-regulating agent, GP531: effects on no-reflow, infarct size, and blood flow following ischemia/ reperfusion in the rabbit. J Cardiovasc Pharmacol Ther. 2010 Mar;15(1):60-7. [2]. Wang M, et al. Acute intravenous infusion of an adenosine regulating agent improves left ventricular function in dogs with advanced heart failure. Cardiovasc Drugs Ther. 2013 Dec;27(6):489-98

Solubility Data

Solubility (In Vitro)

DMSO : ~125 mg/mL (~359.85 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.8788 mL	14.3939 mL	28.7877 mL
	5 mM	0.5758 mL	2.8788 mL	5.7575 mL
	10 mM	0.2879 mL	1.4394 mL	2.8788 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.