| Identification | Back Directory | [Name]
NO-ASPIRIN 1 | [CAS]
175033-36-0 | [Synonyms]
C102148
NCX 4016
NO-ASPIRIN 1
nitroaspirin
Nitric oxide-releasing aspirin
3-(NitroxyMethyl)phenyl 2-acetoxybenzoate
2-Acetoxybenzoate-2-(1-nitroxymethyl)phenyl ester
2-AcetyloxybenzoicAcid3-NitrooxymethylphenylEster
2-(ACETYLOXY)-3-[(NITROOXY)METHYL]PHENYL ESTER, BENZOIC ACID | [Molecular Formula]
C16H13NO7 | [MDL Number]
MFCD00952953 | [MOL File]
175033-36-0.mol | [Molecular Weight]
331.28 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
NO-Aspirin 1 is a hybrid molecule of aspirin and a nitric oxide (NO) donor. It contains an ester linkage, that when cleaved by esterases in the gut, liver, and plasma releases salicylate and an NO-releasing moiety. It also prevents restinosiis, inhibits proliferation of vascular smooth muscle cells, reduces infarct ssize following cardiac ischemia, and exhibits strong chemopreventative effects against colon cancer development. | [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. HenceNCX-4016 is considered a promising therapeutic option against carcinoma. | [IC 50]
COX-1 | [storage]
Store at -20°C | [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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Energy Chemical
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InvivoChem
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