16142-27-1 Usage
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
Different sources of media describe the Uses of 16142-27-1 differently. You can refer to the following data:
1. SIN-1 is a metabolite of the vasodilator molsidomine and is considered to be a peroxynitrite releasing compound
2. 3-Morpholinosydnonimine hydrochloride is a metabolite of the vasodilator Molsidomine (M488002) and is considered to be a peroxynitrite releasing compound. Molsidomine Impurity A.
3. 3-Morpholinosydnonimine hydrochloride has been used:as a peroxynitrite donor standard to study the accumulation of peroxynitrite?in?Arabidopsis thalianato study its effects on nitrosative stress in human brain vascular pericytes and human embryonic kidney cellsas a ROS to study its effects on mouse embryonic fibroblasts
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
Check Digit Verification of cas no
The CAS Registry Mumber 16142-27-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,1,4 and 2 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 16142-27:
(7*1)+(6*6)+(5*1)+(4*4)+(3*2)+(2*2)+(1*7)=81
81 % 10 = 1
So 16142-27-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H11N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5H,1-4,7H2;1H/q+1;/p-1
16142-27-1Relevant articles and documents
Enzyme activated nitric oxide donors
-
, (2008/06/13)
Sugar-modified SIN-1 compositions are provided. The compositions are useful for generating NO in response to hydrolytic activity of a glycosidase specific for the O-glycosidic bond between the sugar and SIN-1 moieties. Pharmaceutical compositions containing the sugar-modified SIN-1 compositions and methods of using the compositions are also provided.
