NO-ASPIRIN 1

Product NameNO-ASPIRIN 1
CAS175033-36-0
MFC16H13NO7
MW331.28
EINECS
MOL File175033-36-0.mol

Chemical Properties

Melting point	61-62°C
Boiling point	499.3±40.0 °C(Predicted)
Density	1.347±0.06 g/cm3(Predicted)
storage temp.	-20°C Freezer
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly)
form	powder
color	white to beige
InChI	1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
InChIKey	IOJUJUOXKXMJNF-UHFFFAOYSA-N
SMILES	CC(OC1=CC=CC=C1C(OC2=CC(CO[N+]([O-])=O)=CC=C2)=O)=O

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Nitroaspirin (NCX 4016) is a nitric oxide (NO) donor and a nitro-derivative of Aspirin, which combines with Nitroaspirin to inhibit cyclooxygenase. Nitroaspirin (NCX 4016) has antithrombotic and anti-platelet properties and acts as a direct and irreversible inhibitor of COX-1. Nitroaspirin (NCX 4016) causes significant induction of cell cycle arrest and apoptosis in Cisplatin-resistant human ovarian cancer cells via down-regulation of EGFR/PI3K/STAT3 signaling and modulation of Bcl-2 family proteins[1][2][3][4].

Definition

ChEBI: 2-acetyloxybenzoic acid [3-(nitrooxymethyl)phenyl] ester is a carbonyl compound.

Biological Activity

NCX 4016 (nitroaspirin) is nitroderivative of aspirin th at combines cyclooxygenase inhibitor with an NO donor. NCX 4016 improves postischemic ventricular dysfunction and to reduce myocardial infarct size in rabbit.', 'NCX-4016 can prevent the progression of cisplatin-resistant human ovarian cancer xenografts in mice. It can also regulate the expression of B-cell lymphoma 2 (Bcl-2) proteins in ovarian cancer cells. Hence, NCX-4016 is considered a promising therapeutic option against carcinoma.

IC 50

COX-1

References

[1] Bertuglia S, et al. Antioxidant activity of nitro derivative of aspirin against ischemia-reperfusion in hamster cheekpouch microcirculation. Am J Physiol Gastrointest Liver Physiol. 2004 Mar;286(3):G437-43. DOI:10.1152/ajpgi.00339.2003
[2] Corazzi T, et al. Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7. DOI:10.1124/jpet.105.089896
[3] Selvendiran K, et al. NCX-4016, a nitro-derivative of aspirin, inhibits EGFR and STAT3 signaling and modulates Bcl-2 proteins in cisplatin-resistant human ovarian cancer cells and xenografts. Cell Cycle. 2008 Jan 1;7(1):81-8. DOI:10.4161/cc.7.1.5103

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