Adenosine, 腺苷

Adenosine is a naturally-occurring organic solvent found in the human body. It has been shown to inhibit fibroid growth and to have an anti-inflammatory effect on the uterus. Adenosine is also a potent endogenous vasodilator, which may be due to its ability to activate adenosine receptors. In addition, it has been demonstrated that adenosine inhibits the synthesis of target enzymes such as collagenase and hyaluronidase. The uptake of adenosine by cells is inhibited by nevirapine, which is an HIV protease inhibitor. This inhibition leads to increased extracellular levels of adenosine, which stimulates phosphorylation of extracellular-regulated kinases (ERKs) and decreases histamine release from mast cells. The ERKs are activated in response to many stimuli including cytokines, growth factors, and stressors such as UV light or heat shock.

Endogenous P1 (adenosine) receptor agonist. Displays neuromodulatory function in addition to showing cardioprotective, anti-inflammatory and antiplatelet action.

Adenosine is a purine nucleoside composed of adenine and ribose linked by a glycosidic linkage. It is an endogenous ligand of a family of four adenosine receptors, which serve diverse roles related to smooth muscle tone, central nervous system regulation, and cardiac function. Adenosine is a precursor for adenosine 5’-monophosphate, adenosine 5’-diphosphate, adenosine 5’-triphosphate, and cyclic AMP.

Adenosine is a purine nucleoside and a building block of RNA and many other biomolecules such as adenosine triphosphate and nicotinamide adenine dinucleotide. In the extracellular space, ecto-5′-nucleotidase (CD73) dephosphorylates adenosine triphosphate (ATP) to produce adenosine. Adenosine has four receptors namely A1R, A2AR A2BR and A3R. Adenosine plays a key role in the osteogenic differentiation. A1R induces osteoclast differentiation and A2AR induces osteoblast differentiation.

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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, also known as adenocard or ade-rib, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Adenosine has been found throughout all human tissues, and has also been detected in most biofluids, including urine, feces, cerebrospinal fluid, and saliva. Within the cell, adenosine is primarily located in the mitochondria and lysosome. Adenosine exists in all eukaryotes, ranging from yeast to humans. Adenosine participates in a number of enzymatic reactions. In particular, Adenosine can be converted into inosine through its interaction with the enzyme adenosine deaminase. In addition, Adenosine can be converted into adenine and ribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. In humans, adenosine is involved in the thioguanine action pathway, the azathioprine action pathway, the methionine metabolism pathway, and the mercaptopurine action pathway. Adenosine is also involved in several metabolic disorders, some of which include S-adenosylhomocysteine (sah) hydrolase deficiency, the hypermethioninemia pathway, adenine phosphoribosyltransferase deficiency (aprt), and adenosine deaminase deficiency. Adenosine is a potentially toxic compound.

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 derives from an adenine.

Title: Adenosine

CAS Registry Number: 58-61-7

CAS Name: 9-b-D-Ribofuranosyl-9H-purin-6-amine

Additional Names: 6-amino-9-b-D-ribofuranosyl-9H-purine; 9-b-D-ribofuranosidoadenine; adenine riboside

Trademarks: Adenocard (Fujisawa); Adenocor (Sanofi Winthrop); Adenoscan (Fujisawa)

Molecular Formula: C10H13N5O4

Molecular Weight: 267.24

Percent Composition: C 44.94%, H 4.90%, N 26.21%, O 23.95%

Literature References: Nucleoside; widely distributed in nature. From yeast nucleic acid: Levene and Bass, Nucleic Acids (New York, 1931) p 163. Structure: Levene, Tipson, J. Biol. Chem. 94, 809 (1932); Bredereck, Ber. 66, 198 (1933); Z. Physiol. Chem. 223, 61 (1934); Gulland, Holiday, J. Chem. Soc. 1936, 765. Cf. Szent-Györgyi, J. Physiol. 68, 213 (1930); Lythgoe et al., J. Chem. Soc. 1947, 355; 1948, 965. Synthesis: Davoll et al., ibid. 1948, 967; H. Vorbrueggen, K. Krolikiewicz, Angew. Chem. Int. Ed. 14, 421 (1975). Crystal structure: T. F. Lai, R. E. Marsh, Acta Crystallogr. B28, 1982 (1972). Conformational properties: D. B. Davies, A. Rabczenko, J. Chem. Soc. Perkin Trans. 2 1975, 1703. Symposium on cardiac electrophysiology, pharmacology and clinical efficacy in supraventricular tachycardia: Prog. Clin. Biol. Res. 230, 1-395 (1987). Reviews: see Adenine.

Properties: Crystals from water, mp 234-235°. [a]D11 -61.7° (c = 0.706 in water); [a]9D -58.2° (c = 0.658 in water). uv max: 260 nm (e 15100). Practically insol in alcohol.

Melting point: mp 234-235°

Optical Rotation: [a]D11 -61.7° (c = 0.706 in water); [a]9D -58.2° (c = 0.658 in water)

Absorption maximum: uv max: 260 nm (e 15100)

Therap-Cat: Antiarrhythmic.

Keywords: Antiarrhythmic.