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.

Not to be confused with adenine.
Adenosine
Clinical data
Trade namesAdenocard; Adenocor; Adenic; Adenoco; Adeno-Jec; Adenoscan; Adenosin; Adrekar; Krenosin
Other namesSR-96225 (developmental code name)
AHFS/Drugs.comMonograph
Pregnancy
category
  • C

(adenosine may be safe to the fetus in pregnant women)

Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityRapidly cleared from circulation via cellular uptake
Protein bindingNo
MetabolismRapidly converted to inosine and adenosine monophosphate
Elimination half-lifecleared plasma <30 seconds; half-life <10 seconds
Excretioncan leave cell intact or can be degraded to hypoxanthine, xanthine, and ultimately uric acid
Identifiers
  • (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.354
Chemical and physical data
FormulaC10H13N5O4
Molar mass267.245 g·mol−1
3D model (JSmol)
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N
  • 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.

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