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SML0414

Sigma-Aldrich

NCX 4040

≥98% (HPLC)

Synonym(s):

2-(Acetyloxy)benzoic acid 4-(nitroxymethyl)phenyl ester, NO-aspirin

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About This Item

Empirical Formula (Hill Notation):
C16H13NO7
CAS Number:
287118-97-2
Molecular Weight:
331.28
MDL number:
MFCD08062164
UNSPSC Code:
12352200
PubChem Substance ID:
329825409
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

−20°C

SMILES string

CC(=O)Oc1ccccc1C(=O)Oc2ccc(CO[N+]([O-])=O)cc2

InChI

1S/C16H13NO7/c1-11(18)23-15-5-3-2-4-14(15)16(19)24-13-8-6-12(7-9-13)10-22-17(20)21/h2-9H,10H2,1H3

InChI key

CTHNKWFUDCMLIQ-UHFFFAOYSA-N

Biochem/physiol Actions

NCX 4040 is a nitric oxide-donating form of aspirin. NCX 4040 inhibits cyclooxygenase activity and releases NO, which can down-regulate COX2 expression and reduce the levels of superoxide accumulation. In the human monocytic cell line THP1, the compound inhibits PGE2 production and cytokine expression, and appears to stabilize IkB by inhibiting proteasome function. NCX 4040 has been shown to induce apoptosis in several tumor cell lines.

Features and Benefits

This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Signal Word

Danger

Hazard Statements

H317,H318,H400

Hazard Classifications

Aquatic Acute 1 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Anna Tesei et al.
Journal of translational medicine, 5, 52-52 (2007-11-01)
Despite numerous studies aimed at verifying the antitumor activity of nitric oxide-releasing nonsteroidal antiflammatory drugs (NO-NSAIDs), little is known about the molecular targets responsible for their antineoplastic properties. In the present study, we investigated the mechanisms underlying the cytotoxicity of
Paul Guedeney et al.
Journal of clinical medicine, 9(3) (2020-03-07)
The respective ischemic and bleeding risks of early aspirin discontinuation following an acute coronary syndrome (ACS) or percutaneous coronary intervention (PCI) remain uncertain. We performed a prospero-registered review of randomized controlled trials (RCTs) comparing a P2Y12 inhibitor-based single antiplatelet strategy
Anna Tesei et al.
Journal of translational medicine, 3(1), 7-7 (2005-02-05)
BACKGROUND: Nitric oxide-releasing nonsteroidal antiinflammatory drugs (NO-NSAIDs) are reported to be safer than NSAIDs because of their lower gastric toxicity. We compared the effect of a novel NO-releasing derivate, NCX 4040, with that of aspirin and its denitrated analog, NCX
Jung Min Song et al.
Carcinogenesis, 39(7), 911-920 (2018-07-10)
Although regular aspirin use has been shown to lower the risk of colorectal cancer, its efficacy against lung cancer is weak or inconsistent. Moreover, aspirin use increases the risk of ulcers and stomach bleeding. In this study, we determined the
Stefania Tacconelli et al.
Clinical pharmacology and therapeutics, 104(1), 111-119 (2018-03-27)
We studied the influence of cardiovascular (CV) risk factors, previous CV events, and cotreatments with preventive medicines, on residual platelet thromboxane (TX)B2 production in 182 patients chronically treated with enteric coated (EC)-aspirin (100 mg/day). The response to aspirin was also verified
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