Amrinone

Crystalline Solid

Solid

Amrinone is a 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure. It has a role as an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.|Amrinone (or inamrinone) is a type 3 pyridine phosphodiesterase inhibitor. It is used in the treatment of congestive heart failure.|Inamrinone is a synthetic bipyridine phosphodiesterase inhibitor with inotropic and vasodilator properties. Inamrinone inhibits type III phosphodiesterase, which is abundant in cardiac and vascular tissues, thereby preventing the degradation of cyclic adenosine monophosphate (cAMP) and increasing intracellular concentrations of this secondary messenger. Elevated levels of cAMP increase the contractile force of the cardiac muscle and produce positive inotropic effects. Although the mechanism of action is not fully understood, inamrinone causes smooth muscle relaxation, resulting in peripheral vasodilation (reduced afterload) and a decreased pulmonary vascular resistance (reduced preload).|A positive inotropic cardiotonic (CARDIOTONIC AGENTS) with vasodilator properties, phosphodiesterase 3 inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.

General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).General procedure: Benzoyl chloride (0.062mL, 0.53mmol, 1 equivalent) was added dropwise to 3-amino-5-(pyridin-4-yl)pyridin-2-one (100mg, 0.53mmol, 1 equivalent) in pyridine (3 mL) and the mixture was stirred for 16h at room temperature. The solvent was removed under reduced pressure and the residue taken up in methanol and filtered to give the desired product as a light-yellow solid (41mg, 27percent).

A selective cAMP phosphodiesterase (PDE-3) inhibitor with positive inotropic and vasodilatory activity. Cardiotonic

Molecular Weight:187.20
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:187.074561919
Monoisotopic Mass:187.074561919
Topological Polar Surface Area:68
Heavy Atom Count:14
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes