Adenosine

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.
Adenosine Diphosphate Adhatoda Adinazolam Adiphenine Adipic Acid

Adenosine
Adenosin.svg
Adenosine spacefilling.png
Systematic (IUPAC) name
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Clinical data
Trade names Adenocard
AHFS/Drugs.com monograph
Pregnancy cat. C
Legal status POM (UK) -only (US)
Routes Intravenous, injection
Pharmacokinetic data
Bioavailability Rapidly cleared from circulation via cellular uptake
Protein binding No
Metabolism Rapidly converted to inosine and adenosine monophosphate
Half-life cleared plasma <30 seconds – half-life <10 seconds
Excretion can leave cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid
Identifiers
CAS number 58-61-7 YesY
ATC code C01EB10
PubChem CID 60961
IUPHAR ligand 2844
DrugBank DB00640
ChemSpider 54923 YesY
UNII K72T3FS567 YesY
KEGG C00212 YesY
ChEBI CHEBI:16335 YesY
ChEMBL CHEMBL477 N
Chemical data
Formula C10H13N5O4 
Mol. mass 267.241 g/mol
 N (what is this?)  (verify)

Adenosine (ADO) is a purine nucleoside comprising a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond.

Adenosine plays an important role in biochemical processes, such as energy transfer — as adenosine triphosphate (ATP) and adenosine diphosphate (ADP) — as well as in signal transduction as cyclic adenosine monophosphate, cAMP. It is also an inhibitory neurotransmitter, believed to play a role in promoting sleep and suppressing arousal.

Adenosine also plays a role in regulation of blood flow to various organs through vasodilation.[1][2][3]