Home Nitros Benzoic acid, 2-(acetyloxy)-, 3-[(nitrooxy)methyl]phenyl ester

Benzoic acid, 2-(acetyloxy)-, 3-[(nitrooxy)methyl]phenyl ester

CAS No.:
175033-36-0
Catalog Number:
AG00203T
Molecular Formula:
C16H13NO7
Molecular Weight:
331.2769
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Purity
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Product Description
Catalog Number:
AG00203T
Chemical Name:
Benzoic acid, 2-(acetyloxy)-, 3-[(nitrooxy)methyl]phenyl ester
CAS Number:
175033-36-0
Molecular Formula:
C16H13NO7
Molecular Weight:
331.2769
MDL Number:
MFCD00952953
IUPAC Name:
[3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
InChI:
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
InChI Key:
IOJUJUOXKXMJNF-UHFFFAOYSA-N
SMILES:
[O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
UNII:
EH04H13L6B
Properties
Complexity:
462  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
331.069g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
331.28g/mol
Monoisotopic Mass:
331.069g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
108A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.9  
Literature
Title Journal
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Nitro-aspirin is a potential therapy for non alcoholic fatty liver disease. European journal of pharmacology 20110601
Nitric oxide (NO)-releasing aspirin exhibits a potent esophagoprotection in experimental model of acute reflux esophagitis. Role of nitric oxide and proinflammatory cytokines. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20110201
Comparison between 3-Nitrooxyphenyl acetylsalicylate (NO-ASA) and O2-(acetylsalicyloxymethyl)-1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (NONO-ASA) as safe anti-inflammatory, analgesic, antipyretic, antioxidant prodrugs. The Journal of pharmacology and experimental therapeutics 20101101
Hyperglycemia-induced platelet activation in type 2 diabetes is resistant to aspirin but not to a nitric oxide-donating agent. Diabetes care 20100601
NCX-1000, a nitric oxide-releasing derivative of UDCA, does not decrease portal pressure in patients with cirrhosis: results of a randomized, double-blind, dose-escalating study. The American journal of gastroenterology 20100501
Effects of aspirin and NO-aspirin (NCX 4016) on platelet function and coagulation in human endotoxemia. Platelets 20100101
NO-donating aspirin and aspirin partially inhibit age-related atherosclerosis but not radiation-induced atherosclerosis in ApoE null mice. PloS one 20100101
Nitro-aspirin inhibits MCF-7 breast cancer cell growth: effects on COX-2 expression and Wnt/beta-catenin/TCF-4 signaling. Biochemical pharmacology 20091115
The differential cell signaling effects of two positional isomers of the anticancer NO-donating aspirin. International journal of oncology 20091001
Comparative effects of aspirin and NO-releasing aspirins on differentiation, maturation and function of human monocyte-derived dendritic cells in vitro. International immunopharmacology 20090701
New antiplatelet drugs: beyond aspirin and clopidogrel. International journal of clinical practice 20090501
Anti-inflammatory, antiproliferative, and cytoprotective activity of NO chimera nitrates of use in cancer chemoprevention. Molecular pharmacology 20081101
Induction of paraoxonase 1 and apolipoprotein A-I gene expression by aspirin. Journal of lipid research 20081001
Fatty aspirin: a new perspective in the prevention of dementia of Alzheimer's type? Current Alzheimer research 20081001
NO-donating aspirin inhibits angiogenesis by suppressing VEGF expression in HT-29 human colon cancer mouse xenografts. Carcinogenesis 20080901
Nitric oxide (NO)-releasing aspirin and (NO) donors in protection of gastric mucosa against stress. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20080801
The nitric oxide-donating derivative of acetylsalicylic acid, NCX 4016, stimulates glucose transport and glucose transporters translocation in 3T3-L1 adipocytes. American journal of physiology. Endocrinology and metabolism 20080701
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 (Georgetown, Tex.) 20080101
NCX-4040, a nitric oxide-releasing aspirin, sensitizes drug-resistant human ovarian xenograft tumors to cisplatin by depletion of cellular thiols. Journal of translational medicine 20080101
Roles of platelet and endothelial cell COX-1 in hypercholesterolemia-induced microvascular dysfunction. American journal of physiology. Heart and circulatory physiology 20071201
Quinone formation as a chemoprevention strategy for hybrid drugs: balancing cytotoxicity and cytoprotection. Chemical research in toxicology 20071201
Nitroaspirin (NCX-4016), an NO donor, is antiangiogenic through induction of loss of redox-dependent viability and cytoskeletal reorganization in endothelial cells. Antioxidants & redox signaling 20071101
Nitric oxide-donating aspirin (NCX 4016) inhibits neointimal thickening in a pig model of saphenous vein-carotid artery interposition grafting: a comparison with aspirin and morpholinosydnonimine (SIN-1). The Journal of thoracic and cardiovascular surgery 20071001
Cardioprotective effects of nitric oxide-aspirin in myocardial ischemia-reperfused rats. American journal of physiology. Heart and circulatory physiology 20070901
Nitric oxide-releasing aspirin: will it say NO to atherothrombosis? International journal of cardiology 20070531
Functional effects of nitric oxide-releasing aspirin on vein conduits of diabetic patients undergoing CABG. International journal of cardiology 20070531
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. Journal of medicinal chemistry 20070517
Effect of aspirin, paracetamol and their nitric oxide donating derivatives on exudate cytokine and PGE2 production in zymosan-induced air pouch inflammation in rats. European journal of pharmacology 20070430
Aspirin is a substrate for paraoxonase-like activity: implications in atherosclerosis. Atherosclerosis 20070401
Tissue factor and nitric oxide: a controversial relationship! Journal of thrombosis and thrombolysis 20070401
Susceptibility of the ocular lens to nitric oxide: implications in cataractogenesis. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20070401
[A novel class of anti-inflammatory and analgesic drugs--NO-donating NSAIDs]. Yao xue xue bao = Acta pharmaceutica Sinica 20070401
Prevention of transient endothelial dysfunction in acute exercise: a friendly fire? Thrombosis and haemostasis 20070301
Prevention by NCX 4016, a nitric oxide-donating aspirin, but not by aspirin, of the acute endothelial dysfunction induced by exercise in patients with intermittent claudication. Thrombosis and haemostasis 20070301
NO-releasing aspirin exerts stronger growth inhibitory effect on Barrett's adenocarcinoma cells than traditional aspirin. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20061201
Chronicles in drug discovery. Drug news & perspectives 20061001
Prevention of postischemic myocardial reperfusion injury by the combined treatment of NCX-4016 and Tempol. Journal of cardiovascular pharmacology 20060901
Molecular characterization of cytotoxic and resistance mechanisms induced by NCX 4040, a novel NO-NSAID, in pancreatic cancer cell lines. Apoptosis : an international journal on programmed cell death 20060801
Nitrogen oxide-releasing aspirin induces histone H2AX phosphorylation, ATM activation and apoptosis preferentially in S-phase cells: involvement of reactive oxygen species. Cell cycle (Georgetown, Tex.) 20060801
Mechanism of action of novel NO-releasing furoxan derivatives of aspirin in human platelets. British journal of pharmacology 20060601
Nitric oxide-releasing aspirin and indomethacin are potent inhibitors against colon cancer in azoxymethane-treated rats: effects on molecular targets. Molecular cancer therapeutics 20060601
NO-donating aspirin induces phase II enzymes in vitro and in vivo. Carcinogenesis 20060401
Nitric oxide and inflammation. Inflammation & allergy drug targets 20060401
NO-NSAIDs: from inflammatory mediators to clinical readouts. Inflammation & allergy drug targets 20060401
The effect of NCX4016 [2-acetoxy-benzoate 2-(2-nitroxymethyl)-phenyl ester] on the consequences of ischemia and reperfusion in the streptozotocin diabetic rat. The Journal of pharmacology and experimental therapeutics 20060301
Nitric oxide-donating aspirin inhibits colon cancer cell growth via mitogen-activated protein kinase activation. The Journal of pharmacology and experimental therapeutics 20060101
Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders. Cardiovascular drug reviews 20060101
Ultracytochemical demonstration of soluble guanylate cyclase activation in rat aorta by NCX4016, a NO-releasing aspirin derivative. Journal of submicroscopic cytology and pathology 20060101
Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). The Journal of pharmacology and experimental therapeutics 20051201
NO-donating aspirin inhibits both the expression and catalytic activity of inducible nitric oxide synthase in HT-29 human colon cancer cells. Biochemical pharmacology 20051001
Ultrastructural investigations on protective effects of NCX 4016 (nitroaspirin) on macrovascular endothelium in diabetic Wistar rats. Journal of submicroscopic cytology and pathology 20050801
Nitroaspirin plus clopidogrel versus aspirin plus clopidogrel against platelet thromboembolism and intimal thickening in mice. Thrombosis and haemostasis 20050301
NSAIDs increase GM-CSF release by human synoviocytes: comparison with nitric oxide-donating derivatives. European journal of pharmacology 20050131
Nitric oxide-releasing aspirin derivative, NCX 4016, promotes reparative angiogenesis and prevents apoptosis and oxidative stress in a mouse model of peripheral ischemia. Arteriosclerosis, thrombosis, and vascular biology 20041101
Risk assessment of endogenous formation of carcinogenic N-nitroso compounds in response to intake of NO-aspirin. Gastroenterology 20040901
Nitroaspirins and morpholinosydnonimine but not aspirin inhibit the formation of superoxide and the expression of gp91phox induced by endotoxin and cytokines in pig pulmonary artery vascular smooth muscle cells and endothelial cells. Circulation 20040831
Co-administration of nitric oxide-aspirin (NCX-4016) and aspirin prevents platelet and monocyte activation and protects against gastric damage induced by aspirin in humans. Journal of the American College of Cardiology 20040804
Theriac found? Nitric oxide-aspirin and the search for the universal cure. Journal of the American College of Cardiology 20040804
Nitric oxide regulates immune cell bioenergetic: a mechanism to understand immunomodulatory functions of nitric oxide-releasing anti-inflammatory drugs. Journal of immunology (Baltimore, Md. : 1950) 20040715
Cooperation between aspirin-triggered lipoxin and nitric oxide (NO) mediates antiadhesive properties of 2-(Acetyloxy)benzoic acid 3-(nitrooxymethyl)phenyl ester (NCX-4016) (NO-aspirin) on neutrophil-endothelial cell adherence. The Journal of pharmacology and experimental therapeutics 20040601
Nitric oxide release and distribution following oral and intraperitoneal administration of nitroaspirin (NCX 4016) in the rat. Life sciences 20040514
Chemiluminescence and LC-MS/MS analyses for the study of nitric oxide release and distribution following oral administration of nitroaspirin (NCX 4016) in healthy volunteers. Journal of pharmaceutical and biomedical analysis 20040416
Mechanisms of nonsteroidal anti-inflammatory drug-induced gastrointestinal injury and repair: a window of opportunity for cyclooxygenase-inhibiting nitric oxide donors. Canadian journal of gastroenterology = Journal canadien de gastroenterologie 20040401
The influence on human osteoblasts in vitro of non-steroidal anti-inflammatory drugs which act on different cyclooxygenase enzymes. The Journal of bone and joint surgery. British volume 20040401
Antioxidant activity of nitro derivative of aspirin against ischemia-reperfusion in hamster cheek pouch microcirculation. American journal of physiology. Gastrointestinal and liver physiology 20040301
Polymorphism of NCX4016, an NO-releasing derivative of acetylsalicylic acid. Journal of pharmaceutical sciences 20040301
NO-donating aspirin inhibits intestinal carcinogenesis in Min (APC(Min/+)) mice. Biochemical and biophysical research communications 20040116
Aspirin, but not NO-releasing aspirin (NCX-4016), interacts with selective COX-2 inhibitors to aggravate gastric damage and inflammation. American journal of physiology. Gastrointestinal and liver physiology 20040101
Antiplatelet agents. The hematology journal : the official journal of the European Haematology Association 20040101
No-Aspirin (NCX 4016). Gastroenterology 20031201
Effect of nitric oxide-donating agents on human monocyte cyclooxygenase-2. Biochemical and biophysical research communications 20031128
Nitric oxide-donating aspirin inhibits beta-catenin/T cell factor (TCF) signaling in SW480 colon cancer cells by disrupting the nuclear beta-catenin-TCF association. Proceedings of the National Academy of Sciences of the United States of America 20031028
Single oral dose study of two isosorbide-based aspirin prodrugs in the dog. The Journal of pharmacy and pharmacology 20031001
Nitric oxide-releasing aspirin inhibits vasoconstriction in perfused tail artery of normotensive and spontaneously hypertensive rats. European journal of pharmacology 20030905
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Good news about gut-friendly aspirin. Harvard health letter 20030801
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NCX 4016, a nitric oxide-releasing aspirin derivative, exhibits a significant antiproliferative effect and alters cell cycle progression in human colon adenocarcinoma cell lines. International journal of oncology 20030601
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NCX 4016, a nitric oxide-releasing aspirin, modulates adrenergic vasoconstriction in the perfused rat tail artery. British journal of pharmacology 20020901
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NCX4016 (NO-aspirin) reduces infarct size and suppresses arrhythmias following myocardial ischaemia/reperfusion in pigs. British journal of pharmacology 20020401
Nitrosylhemoglobin, an unequivocal index of nitric oxide release from nitroaspirin: in vitro and in vivo studies in the rat by ESR spectroscopy. Journal of pharmaceutical and biomedical analysis 20011101
NCX4016 (NO-Aspirin) has multiple inhibitory effects in LPS-stimulated human monocytes. British journal of pharmacology 20011001
Vasorelaxant effect of nitric oxide releasing steroidal and nonsteroidal anti-inflammatory drugs. British journal of pharmacology 20010801
Vasorelaxant effects of a nitric oxide-releasing aspirin derivative in normotensive and hypertensive rats. British journal of pharmacology 20010801
Low gastric toxicity of nitric oxide-releasing aspirin, NCX-4016, in rats with cirrhosis and arthritis. Digestive diseases and sciences 20010801
Effect of cyclooxygenase-2 inhibitor (celecoxib) on the infarcted heart in situ. Pharmacology 20010701
NO-releasing NSAIDs are caspase inhibitors. Trends in immunology 20010501
Nitro-aspirin (NCX4016) reduces brain damage induced by focal cerebral ischemia in the rat. Neuroscience letters 20010420
The nitroderivative of aspirin, NCX 4016, reduces infarct size caused by myocardial ischemia-reperfusion in the anesthetized rat. The Journal of pharmacology and experimental therapeutics 20010401
NCX4016 (NO-aspirin) inhibits thromboxane biosynthesis and tissue factor expression and activity in human monocytes. Medical science monitor : international medical journal of experimental and clinical research 20010101
Properties