Adenosine

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.

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)
Physiological data
Source tissues	Primarily liver
Metabolism	Rapidly converted to inosine and adenosine monophosphate
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Rapidly cleared from circulation via enzyme degradation
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 Y
PubChem CID	60961
IUPHAR/BPS	2844
DrugBank	DB00640 Y
ChemSpider	54923 Y
UNII	K72T3FS567
KEGG	C00212 Y
ChEBI	CHEBI:16335 Y
ChEMBL	ChEMBL477 Y
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 Y Key:OIRDTQYFTABQOQ-KQYNXXCUSA-N Y
NY (what is this?)  (verify)

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) and as a radical in the radical SAM enzymes.