Description
As the active metabolite of molsidomine, SIN-
1 (chloride) is a potent vasorelaxant and inhibitor of platelet aggregation. It produces both NO and superoxide and can therefore be used to generate peroxynitrite under physiological conditions.
Chemical Properties
White Crystalline Solid
Uses
3-Morpholinosydnonimine hydrochloride has been used:
- as a peroxynitrite donor standard to study the accumulation of peroxynitrite?in?Arabidopsis thaliana
- to study its effects on nitrosative stress in human brain vascular pericytes and human embryonic kidney cells
- as a ROS to study its effects on mouse embryonic fibroblasts
Uses
SIN-1 is a metabolite of the vasodilator molsidomine and is considered to be a peroxynitrite releasing compound
Uses
3-Morpholinosydnonimine hydrochloride is a metabolite of the vasodilator Molsidomine (M488002) and is considered to be a peroxynitrite releasing compound. Molsidomine Impurity A.
Indications
Linsidomine (SIN-1) is an active metabolite of the
antianginal drug molsidomine. Its mechanism of action
upon the corpus cavernosum involves the release of nitric
oxide. Injected intracavernosally it can produce penile
erections, but its clinical usefulness has not been
fully established.
Biological Activity
This compound (the active product of the prodrug SIN-10, molsidomine) acts as a vasodilator and inhibitor of platelet aggregation; longer acting than nitroprusside or nitroglycerin. Decreases myocardial necrosis and reperfusion-induced endothelial dysfunction in models of myocardial ischemia-reperfusion.
Biochem/physiol Actions
3-Morpholinosydnonimine participates in the inhibition of cysteine proteases.
References
1) Nishikawa?et al.?(1982)?Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites;?J. Pharmacol. Exp. Ther.?220?183
2) Hogg?et al.?(1992)?Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide; Biochem. J.?281?419
3) Kirsch?et al.?(1998)?Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines. Implications for a general mechanism.; J. Biol. Chem.?273?12716
4) Priora?et al.?(2011)?In vitro inhibition of human and rat platelets by NO donors nitrosoglutathione sodium nitroprusside and SIN-1 through activation of cGMP independent pathways; Pharmacol. Res.?64?289
5) Ren?et al.?(2017)?Identification of a New Function of Cardiovascular Disease Drug 3-Morpholinosydnonimine Hydrochloride as an Amyloid-β Aggregation Inhibitor;?ACS Omega.?2?243
