175033-36-0

Basic information

• Product Name: NO-ASPIRIN 1
• Synonyms: 2-(ACETYLOXY)-3-[(NITROOXY)METHYL]PHENYL ESTER, BENZOIC ACID;NCX 4016;NO-ASPIRIN 1;2-AcetyloxybenzoicAcid3-NitrooxymethylphenylEster;nitroaspirin;2-Acetoxybenzoate-2-(1-nitroxymethyl)phenyl ester;C102148;Nitric oxide-releasing aspirin
• CAS NO: 175033-36-0
• Molecular Formula: C₁₆H₁₃NO₇
• Molecular Weight: 331.28
• Product Categories: Aromatics Compounds;Aromatics;Inhibitors;Nitric Oxide Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 175033-36-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 61-62°C
• Boiling Point: 499.3°Cat760mmHg
• Flash Point: 214.3°C
• Appearance: /
• Density: 1.347g/cm³
• Vapor Pressure: 4.21E-10mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: NO-ASPIRIN 1(CAS DataBase Reference)
• NIST Chemistry Reference: NO-ASPIRIN 1(175033-36-0)
• EPA Substance Registry System: NO-ASPIRIN 1(175033-36-0)

Safety Data

• Hazardous Substances Data: 175033-36-0(Hazardous Substances Data)

Usage

Description

NO-ASPIRIN 1 is a hybrid molecule of aspirin and a nitric oxide (NO) donor, designed to provide the benefits of both components. It is an off-white solid that contains an ester linkage, which, when cleaved by esterases in the gut, liver, and plasma, releases salicylate and an NO-releasing moiety. This unique combination of properties makes NO-ASPIRIN 1 a promising candidate for various medical applications.

Uses

Used in Cardiovascular Applications:
NO-ASPIRIN 1 is used as an antiplatelet agent for preventing blood clot formation and reducing the risk of heart attacks and strokes. The nitric oxide-releasing moiety enhances vasodilation, while the salicylate component provides anti-inflammatory and analgesic effects.
Used in Restenosis Prevention:
NO-ASPIRIN 1 is used as a preventive agent for inhibiting the re-narrowing of blood vessels after angioplasty or stenting procedures. Its NO-releasing property helps maintain the patency of the treated vessels and reduces the likelihood of restenosis.
Used in Vascular Smooth Muscle Cell Proliferation Inhibition:
NO-ASPIRIN 1 is used as an inhibitor for preventing the proliferation of vascular smooth muscle cells, which can contribute to the development of atherosclerosis and other vascular diseases.
Used in Cardiac Ischemia:
NO-ASPIRIN 1 is used as a therapeutic agent for reducing infarct size following cardiac ischemia, protecting the heart from damage and improving recovery.
Used in Cancer Prevention:
NO-ASPIRIN 1 is used as a chemopreventative agent for inhibiting the development of colon cancer. Its anti-inflammatory and NO-releasing properties contribute to its cancer-preventing effects.
Used in Pharmaceutical Industry:
NO-ASPIRIN 1 is used as an active pharmaceutical ingredient for the development of novel drugs targeting various cardiovascular and oncological conditions.
Used in Research and Development:
NO-ASPIRIN 1 is used as a research tool for studying the effects of nitric oxide donors and aspirin on various biological processes, including inflammation, blood clotting, and cancer development.

InChI:InChI=1/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

Upstream product

• 287118-99-4 2-(acetyloxy)benzoic acid 3-(chloromethyl)-phenyl ester 
• 50-78-2 aspirin 
• 203065-55-8 2-(acetyloxy)benzoic acid 3-(formyl)phenyl ester 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 287118-98-3 NCX 4017 

Relevant articles and documents

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

Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO 2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

Nitric oxide-donating non-steroidal anti-inflammatory drugs: The case of nitroderivatives of aspirin

Nitric oxide (NO) acts as a key signalling mechanism in a number of cells and tissues in the mammalian organism. Modulation of the biosynthesis of NO has emerged to be relevant to the treatment of a variety of human diseases. In the attempt to reduce the serious side effects of non-steroidal anti-inflammatory drugs (NSAIDs), especially in the gastrointestinal tract, a NO-releasing moiety has been linked to conventional NSAIDs. A prototypical example is that of NO-releasing derivatives of aspirin. Thanks to the cytoprotective action of NO such compounds do not produce gastric damage and are emerging as an interesting novel group of drugs for their unique pharmacological properties.