*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!
Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine.
The structure of adenosine was first described in 1931, though the vasodilating effects were not described in literature until the 1940s. Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson]. Adenosine is also indicated in the treatment of supraventricular tachycardia. Adenosine was granted FDA approval on 30 October 1989.
Adenosine is a metabolite found in or produced by Escherichia coli .
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Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist.
Adenosine is a natural product found in Acanthus ilicifolius, Acanthus ebracteatus, and other organisms with data available.
Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities. Phosphorylated forms of adenosine play roles in cellular energy transfer, signal transduction and the synthesis of RNA.
Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate and adenosine diphosphate . It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent.
Adenosine is a metabolite found in or produced by Saccharomyces cerevisiae.
A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter.
See also: Adenosine; Niacinamide ; Adenosine; Glycerin ; Adenosine; arbutin ... View More ...
Computed Properties
Molecular Weight:
267.24 g/mol
XLogP3:
-1.1
Hydrogen Bond Donor Count:
4
Hydrogen Bond Acceptor Count:
8
Rotatable Bond Count:
2
Exact Mass:
267.09675391 g/mol
Monoisotopic Mass:
267.09675391 g/mol
Topological Polar Surface Area:
140 Ų
Heavy Atom Count:
19
Formal Charge:
0
Complexity:
335
Isotope Atom Count:
0
Defined Atom Stereocenter Count:
4
Undefined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Covalently-Bonded Unit Count:
1
Compound Is Canonicalized:
Yes
Related Compounds
Adenosine Phosphate
Adenosine
Adenosine-5'-triphosphate
Vidarabine
5'-Deoxy-5'-methylthioadenosine
Cladribine
Adenosine cyclic phosphate
Adenosine-5'-diphosphate
Ribavirin
2'-Deoxyadenosine
Acadesine
Fludarabine
2'-Deoxyadenosine 5'-triphosphate
Clofarabine
Fludarabine Phosphate
hazard signal
Warning
hazard classes and categories
Skin Irrit. 2 (97.14%)
Eye Irrit. 2A (97.14%)
precautionary statement codes
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364
Adenosine slows conduction time through the AV node and can interrupt the reentry pathways through the AV node, resulting in the restoration of normal sinus rhythm in patients with paroxysmal supraventricular tachycardia , including PSVT associated with Wolff-Parkinson-White Syndrome. This effect may be mediated through the drug's activation of cell-surface A<sub>1</sub> and A<sub>2</sub> adenosine receptors. Adenosine also inhibits the slow inward calcium current and activation of adenylate cyclase in smooth muscle cells, thereby causing relaxation of vascular smooth muscle. By increasing blood flow in normal coronary arteries with little or no increase in stenotic arteries , adenosine produces a relative difference in thallous chloride TI 201 uptake in myocardium supplied by normal verus stenotic coronary arteries.
symptoms
health effects
Chronically high levels of adeonsine are associated with Adenosine Deaminase Deficiency.
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