Page last updated: 2024-11-07

nitroaspirin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

nitroaspirin: a nitric oxide donor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119032
CHEMBL ID374385
CHEBI ID125482
SCHEMBL ID19524
MeSH IDM0383373

Synonyms (44)

Synonym
ncx-4016
m-no-aspirin
m-no-asa
no-asa
2-acetoxybenzoate-2-(1-nitroxymethyl)phenyl ester
benzoic acid, 2-(acetyloxy)-, 3-((nitrooxy)methyl)phenyl ester
2-acetoxybenzoic acid 3-nitrooxymethylphenyl ester
3-(nitroxymethyl)phenyl 2-acetoxybenzoate
nitroaspirin
ncx 4016
2-((nitrooxy)methyl)phenyl 2-(acetyloxy)benzoate
benzoic acid, 2-(acetyloxy)-, 2-((nitrooxy)methyl)phenyl ester
3-((nitrooxy)methyl)phenyl 2-(acetyloxy)benzoate
nitric oxide-releasing aspirin
CHEMBL374385
no-aspirin 1
[3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
175033-36-0
unii-eh04h13l6b
eh04h13l6b ,
FT-0673020
BRD-K08807999-001-01-6
AKOS025294730
CCG-208118
SCHEMBL19524
2-(acetyloxy)-(3-(nitroxymethyl)phenyl)benzoic acid
ncx4016
gtpl9018
3-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
CHEBI:125482
ncx 4016, >=98% (hplc)
2-acetoxy benzoic acid-3-nitrooxymethyl phenyl ester
J-011058
DB12445
(2-{[(1s)-1-(5-fluoro(2-pyridyl))ethyl]amino}-5-chloropyrimidin-4-yl)[5-(methylethoxy)pyrazol-3-yl]amine
BCP24321
Q3877377
DTXSID60938618
CS-0086219
HY-123823
benzoic acid, 2-(acetyloxy)-, 3-[(nitrooxy)methyl]phenyl ester
3-((nitrooxy)methyl)phenyl 2-acetoxybenzoate
3-((nitrooxy)methyl)phenyl2-acetoxybenzoate
AKOS040742306

Research Excerpts

Effects

ExcerptReferenceRelevance
"Nitroaspirin has shown a number of significant advantages over the presently available antiplatelet agents; however, only clinical studies will say whether nitroaspirin represents a step forward in antithrombotic treatment."( NCX4016: a novel antithrombotic agent.
Gresele, P; Mezzasoma, AM; Momi, S, 2003
)
1.04

Toxicity

ExcerptReferenceRelevance
"We compared the gastric toxic effect of aspirin (ASA) in both normal and diabetic rats, with that of NCX-4016, a derivative of ASA with nitric oxide (NO) releasing moiety."( Lack of gastric toxicity of nitric oxide-releasing aspirin, NCX-4016, in the stomach of diabetic rats.
Fujita, A; Takeuchi, K; Tashima, K; Umeda, M, 2000
)
0.31
"The gastric toxic effects of aspirin (ASA) and NCX-4016, a nitric oxide (NO)-releasing ASA, were compared in normal, cirrhotic, and arthritic rats."( Low gastric toxicity of nitric oxide-releasing aspirin, NCX-4016, in rats with cirrhosis and arthritis.
Kato, S; Komoike, Y; Suzuki, K; Takeuchi, K; Ukawa, H, 2001
)
0.31

Bioavailability

ExcerptReferenceRelevance
" The pharmacokinetics of in vivo aspirin- and NO- released by NCX 4016, as well as the bioavailability of the two molecules, were not yet adequately studied."( Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders.
Gresele, P; Momi, S, 2006
)
0.33
" Additionally, it increases NO bioavailability as a vascular level, and it may have the antiatherogenic properties of endogenously produced NO."( Nitric oxide-releasing aspirin: will it say NO to atherothrombosis?
Antoniades, C; Stefanadis, C; Tousoulis, D, 2007
)
0.34
" However, the concomitant production of superoxide and other reactive oxygen species (ROS) during I/R may diminish the bioavailability of NO and hence compromise the beneficial effects."( Prevention of postischemic myocardial reperfusion injury by the combined treatment of NCX-4016 and Tempol.
Colantuono, G; Khan, M; Kumbala, D; Kuppusamy, P; Kutala, VK; Mandal, R; Potaraju, V, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbonyl compoundAny compound containing the carbonyl group, C=O. The term is commonly used in the restricted sense of aldehydes and ketones, although it actually includes carboxylic acids and derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID286679Inhibition of serum-induced expression of cyclin D in human SW480 cells after 5 hrs2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin.
AID286677Apoptosis induction in human HT29 cells after 24 hrs2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (125)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's10 (8.00)18.2507
2000's103 (82.40)29.6817
2010's12 (9.60)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.24

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.24 (24.57)
Research Supply Index4.92 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (7.09%)5.53%
Reviews17 (13.39%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other101 (79.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (3)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Multicenter, Double-blind, Randomized, Parallel Group Study to Assess the Effect of NCX4016 vs Placebo on Walking Distance in Patients With Peripheral Arterial Occlusive Disease at Leriche-Fontaine Stage II [NCT01256775]Phase 2442 participants (Actual)Interventional2003-09-30Completed
A Pilot, Randomised, Double-blind, Cross-over Study to Assess the Renal and Systemic Effects of NCX4016 in Patients With Type 2 Diabetes and Early Nephropathy [NCT00157508]Phase 213 participants Interventional2003-03-31Terminated
Phase I Multiple-Dose Safety, Pharmacokinetic and Pharmacodynamic Clinical Study of Nitric Oxide Releasing Aspirin (NCX 4016) [NCT00331786]Phase 1240 participants (Anticipated)Interventional2006-07-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]