Adenosine

Adenosine
Clinical data
Trade names	Adenocard; Adenocor; Adenic; Adenoco; Adeno-Jec; Adenoscan; Adenosin; Adrekar; Krenosin
Other names	SR-96225 (developmental code name)
AHFS/Drugs.com	Monograph
Pregnancy; category	C; (adenosine may be safe to the fetus in pregnant women)
Routes of; administration	Intravenous
ATC code	C01EB10 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Rapidly cleared from circulation via cellular uptake
Protein binding	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
	IUPAC name (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;
CAS Number	58-61-7 ;
PubChem CID	60961;
IUPHAR/BPS	2844;
DrugBank	DB00640 ;
ChemSpider	54923 ;
UNII	K72T3FS567;
KEGG	C00212 ;
ChEBI	CHEBI:16335 ;
ChEMBL	ChEMBL477 ;
CompTox Dashboard (EPA)	DTXSID1022558 ;
ECHA InfoCard	100.000.354
Chemical and physical data
Formula	C10H13N5O4
Molar mass	267.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N;
	InChI InChI=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 ; Key:OIRDTQYFTABQOQ-KQYNXXCUSA-N ;
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Adenosine (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-N₉-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 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 arrhythmias.

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^[1]) and as a radical in the radical SAM enzymes.^[2]

^ Butler P, Kräutler B (2006). "Biological Organometallic Chemistry of B12". Bioorganometallic Chemistry. Topics in Organometallic Chemistry. Vol. 17. pp. 1–55. doi:10.1007/3418_004. ISBN 3-540-33047-X.
^ Nelson DL, Cox MM (2005). Principles of Biochemistry (4th ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.

[1] Butler P, Kräutler B (2006). "Biological Organometallic Chemistry of B12". Bioorganometallic Chemistry. Topics in Organometallic Chemistry. Vol. 17. pp. 1–55. doi:10.1007/3418_004. ISBN 3-540-33047-X.

[2] Nelson DL, Cox MM (2005). Principles of Biochemistry (4th ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.

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