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

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.

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

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

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.