Editing Adenosine (section)

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Distinguish|adenine}}
{{Drugbox
| Verifiedfields = changed
| source_tissues = Primarily liver
| verifiedrevid = 477242323
| IUPAC_name = (2''R'',3''R'',4''S'',5''R'')-2-(6-amino-9''H''-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
| image = Adenosin.svg
| image_class = skin-invert-image
| image2 = Adenosine-3D-balls.png
<!--Clinical data-->| tradename = Adenocard; Adenocor; Adenic; Adenoco; Adeno-Jec; Adenoscan; Adenosin; Adrekar; Krenosin
| Drugs.com = {{drugs.com|monograph|adenosine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = C
(adenosine may be safe to the fetus in pregnant women)
| legal_status = Rx-only
| routes_of_administration = Intravenous
<!--Pharmacokinetic data-->| bioavailability = Rapidly cleared from circulation via enzyme degradation
| protein_bound = No
| metabolism = Rapidly converted to inosine and adenosine monophosphate
| elimination_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_Ref = {{cascite|correct|CAS}}
| CAS_number = 58-61-7
| ATC_prefix = C01
| ATC_suffix = EB10
| PubChem = 60961
| IUPHAR_ligand = 2844
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00640
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 54923
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K72T3FS567
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00212
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16335
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 477
| synonyms = SR-96225 (developmental code name)
<!--Chemical data-->| C = 10
| H = 13
| N = 5
| O = 4
| smiles = n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OIRDTQYFTABQOQ-KQYNXXCUSA-N
}}

'''Adenosine''' ([[nucleoside#List of nucleosides and corresponding nucleobases|symbol]] '''A''') is an [[organic compound]] that occurs widely in nature in the form of diverse derivatives. The molecule consists of an [[adenine]] attached to a [[ribose]] via a β-N<sub>9</sub>-[[glycosidic bond]]. Adenosine is one of the four [[nucleoside]] building blocks of [[RNA]] (and its derivative [[deoxyadenosine]] is a building block of [[DNA]]), which are essential for all life on Earth. Its derivatives include the energy carriers [[adenosine triphosphate|adenosine mono-, di-, and triphosphate]], also known as AMP/ADP/ATP. [[Cyclic adenosine monophosphate]] (cAMP) is pervasive in [[signal transduction]]. Adenosine is used as an intravenous medication for some [[cardiac arrhythmia]]s.

'''Adenosyl''' (abbreviated '''Ado''' or '''5'-dAdo''') is the chemical group formed by removal of the 5′-hydroxy (OH) group. It is found in [[adenosylcobalamin]] (an active form of [[vitamin B12]]<ref>{{Cite book |doi=10.1007/3418_004|chapter=Biological Organometallic Chemistry of B12|title=Bioorganometallic Chemistry|series=Topics in Organometallic Chemistry|year=2006| vauthors = Butler P, Kräutler B |volume=17|pages=1–55|isbn=3-540-33047-X}}</ref>) and as a radical in the [[radical SAM]] enzymes.<ref>{{Lehninger4th}}</ref>