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Identification
Name Adenosine
Accession Number DB00640 (APRD00132)
Type small molecule
Groups approved
Description

A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
2'-Deoxyadenosine
Adenine Deoxy Nucleoside
Adenine Deoxyribonucleoside
Adenine Deoxyribose
Adenine Nucleoside
Adenine Riboside
Adenyldeoxyriboside
Deoxyadenosine
Desoxyadenosine
MEDR-640
USAF CB-10
First Prev Next Last
Salts Not Available
Brand names
Name Company
Adenocard
Adenocor
Adenoscan
Adenosin
Adensoine
Boniton
Myocol
Nucleocardyl
Pallacor
Sandesin
Brand mixtures Not Available
Categories
  • Analgesics
  • Vasodilator Agents
  • Antiarrhythmic Agents
  • Anti-Arrhythmia Agents
  • Cardiac drugs
CAS number 58-61-7
Weight Average: 267.2413
Monoisotopic: 267.096753929
Chemical Formula C10H13N5O4
InChI Key InChIKey=OIRDTQYFTABQOQ-KQYNXXCUSA-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
Plain Text
IUPAC Name
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
Plain Text
Mass Spec show (9.12 KB)
Taxonomy
Kingdom Organic
Classes
  • Purines and Purine Derivatives
  • Carbohydrates
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Ethers
  • Alcohols and Polyols
  • Pyrimidines and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Furans
  • Cyanamides
  • Carbohydrates
Pharmacology
Indication Used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (PVST), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (SVT). Also used as an adjunct to thallous chloride TI 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex SVT.
Pharmacodynamics Adenosine is an endogenous nucleoside occurring in all cells of the body and is not chemically related to other antiarrhythmic drugs. Adenosine may exert its pharmacologic effects by activation of purine (cell surface A1 and A2 adenosine) receptors, as well as relax vascular smooth muscles through the reduction in calcium uptake by inhibition of slow inward calcium current and activation of adenylate cyclase in smooth muscle cells. Adenosine may reduce vascular tone by modulation of sympathetic neurotransmission. The drug also has negative chronotropic, dromotropic, and inotropic effects on the heart by slowing conduction time throught he AV node and interrupting AV nodal reentry pathways. Adenosine is a potent vasodilator in most vascular beds, but vasoconstriction is produced in renal afferent arterioles and hepatic veins. The drug produces a net mild to moderate reduction in systolic, diastolic, and mean arterial blood pressure and a reflex increase in heart rate. Adenosine is antagonized competitively by methylxanthines such as caffeine and theophylline, and potentiated by blockers of nucleoside transport such as dipyridamole. Adenosine is not blocked by atropine.
Mechanism of action Adenosine slows conduction time through the AV node and can interrupt the reentry pathways through the AV node, resulting in the restoration of normal sinus rhythm in patients with paroxysmal supraventricular tachycardia (PSVT), including PSVT associated with Wolff-Parkinson-White Syndrome. This effect may be mediated through the drug's activation of cell-surface A1 and A2 adenosine receptors. Adenosine also inhibits the slow inward calcium current and activation of adenylate cyclase in smooth muscle cells, thereby causing relaxation of vascular smooth muscle. By increasing blood flow in normal coronary arteries with little or no increase in stenotic arteries (with little to no increase in stenotic arteries), adenosine produces a relative difference in thallous (thallium) chloride TI 201 uptake in myocardium supplied by normal verus stenotic coronary arteries.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Intracellular adenosine is rapidly metabolized either via phosphorylation to adenosine monophosphate by adenosine kinase, or via deamination to inosine by adenosine deaminase in the cytosol.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Adenosine
    		Adenosine monophosphate Details
    Adenosine
      		Inosine Details
      Route of elimination Not Available
      Half life Less than 10 secs
      Clearance Not Available
      Toxicity Not Available
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers
      • Astellas pharma us inc
      • Akorn inc
      • App pharmaceuticals llc
      • Baxter healthcare corp
      • Bedford laboratories div ben venue laboratories inc
      • Gland pharma ltd
      • Luitpold pharmaceuticals inc
      • Strides arcolab ltd
      • Teva parenteral medicines inc
      • Wockhardt ltd
      Packagers
      Dosage forms
      Form Route Strength
      Liquid Intravenous
      Solution Intravenous
      Prices
      Unit description Cost Unit
      Adenosine-5 monophosphate 19.74 USD g
      Adenosine powder 15.86 USD g
      Adenoscan 3 mg/ml vial 10.09 USD ml
      Adenosine 12 mg/4 ml vial 8.44 USD ml
      Adenosine 6 mg/2 ml vial 8.1 USD ml
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents
      Country Patent Number Approved Expires (estimated)
      United States 5731296 1995-03-24 2015-03-24
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 235.5 °C PhysProp
      water solubility 8230 mg/L Not Available
      logP -1.05 HANSCH,C ET AL. (1995)
      Predicted Properties
      Property Value Source
      water solubility 1.40e+01 g/l ALOGPS
      logP -1.2 ALOGPS
      logP -2.1 ChemAxon
      logS -1.3 ALOGPS
      pKa (strongest acidic) 12.45 ChemAxon
      pKa (strongest basic) 4.99 ChemAxon
      physiological charge 0 ChemAxon
      hydrogen acceptor count 8 ChemAxon
      hydrogen donor count 4 ChemAxon
      polar surface area 139.54 ChemAxon
      rotatable bond count 2 ChemAxon
      refractivity 63.2 ChemAxon
      polarizability 25.27 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference Not Available
      External Links
      Resource Link
      KEGG Drug D00045 Link_out
      KEGG Compound C00212 Link_out
      PubChem Compound 60961 Link_out
      PubChem Substance 46508728 Link_out
      ChemSpider 54923 Link_out
      ChEBI 16335 Link_out
      ChEMBL 16335 Link_out
      Therapeutic Targets Database DAP000223 Link_out
      PharmGKB PA448049 Link_out
      HET 101 Link_out
      Drug Product Database 2243435 Link_out
      RxList http://www.rxlist.com/cgi/generic3/adenos.htm Link_out
      Drugs.com http://www.drugs.com/cdi/adenosine.html Link_out
      Wikipedia http://en.wikipedia.org/wiki/Adenosine Link_out
      ATC Codes
      • C01EB10
      AHFS Codes
      • 92:00.00
      PDB Entries Not Available
      FDA label show (154 KB)
      MSDS show (72.7 KB)
      Interactions
      Drug Interactions
      Drug Interaction
      Aminophylline This xanthine decreases the effect of adenosine
      Caffeine Caffeine may diminish the therapeutic effect of adenosine. Specific management recommendations vary slightly depending on specific adenosine product used (i.e., therapeutic vs. diagnostic use of adenosine). Significantly higher adenosine doses, or alternative agents, may be required. Monitor for decreased therapeutic effects of adenosine if the patient is already receiving caffeine. Discontinue caffeine in advance (5 half-lives, or approximately 24 hours, is specifically recommended) of scheduled diagnostic use of adenosine (e.g., for radionuclide imaging studies) whenever possible.
      Dipyridamole Dipyridamole may increase the effect/toxicity of adenosine.
      Dyphylline This xanthine decreases the effect of adenosine
      Oxtriphylline This xanthine decreases the effect of adenosine
      Theophylline Theophylline may decrease the effect of adenosine.
      Food Interactions
      • Avoid caffeine containing foods and drinks.
      Targets

      1. Adenosine A2a receptor

      Pharmacological action: yes
      Actions: agonist

      Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

      Organism class: human
      UniProt ID: P29274 Link_out
      Gene: ADORA2A Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. Pubmed
      2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. Pubmed
      3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. Pubmed
      4. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. Pubmed
      5. Kreckler LM, Gizewski E, Wan TC, Auchampach JA: Adenosine suppresses lipopolysaccharide-induced tumor necrosis factor-alpha production by murine macrophages through a protein kinase A- and exchange protein activated by cAMP-independent signaling pathway. J Pharmacol Exp Ther. 2009 Dec;331(3):1051-61. Epub 2009 Sep 11. Pubmed
      6. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. Epub 2010 Feb 5. Pubmed
      7. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. Pubmed
      8. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. Pubmed

      2. Adenosine A2b receptor

      Pharmacological action: yes
      Actions: agonist

      Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

      Organism class: human
      UniProt ID: P29275 Link_out
      Gene: ADORA2B Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. Pubmed
      2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. Pubmed
      3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. Pubmed
      4. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. Pubmed
      5. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. Epub 2010 Feb 5. Pubmed
      6. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. Pubmed
      7. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. Pubmed

      3. Adenosine A3 receptor

      Pharmacological action: yes
      Actions: agonist

      Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction

      Organism class: human
      UniProt ID: P33765 Link_out
      Gene: ADORA3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
      2. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. Pubmed
      3. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. Pubmed
      4. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. Pubmed
      5. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. Pubmed
      6. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. Epub 2010 Feb 5. Pubmed
      7. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. Pubmed
      8. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. Pubmed

      4. Adenosine A1 receptor

      Pharmacological action: yes
      Actions: agonist

      Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase

      Organism class: human
      UniProt ID: P30542 Link_out
      Gene: ADORA1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. Pubmed
      2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. Pubmed
      3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. Pubmed
      4. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. Epub 2010 Feb 5. Pubmed
      5. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. Pubmed
      6. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. Pubmed
      Enzymes

      1. Adenosine deaminase

      Actions: substrate

      Adenosine + H(2)O = inosine + NH(3)

      UniProt ID: P00813 Link_out
      Gene: ADA Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Kopff M, Kopff A, Puczkowski S: [Adenosine deaminase: isoenzymes ADA1 and ADA2]. Pol Merkur Lekarski. 1997 Dec;3(18):288-90. Pubmed

      2. Adenosine kinase

      Actions: substrate

      ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides

      UniProt ID: P55263 Link_out
      Gene: ADK Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Boison D: Adenosine kinase, epilepsy and stroke: mechanisms and therapies. Trends Pharmacol Sci. 2006 Dec;27(12):652-8. Epub 2006 Oct 23. Pubmed
      Transporters

      1. Solute carrier family 28 member 3

      Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazauridine

      UniProt ID: Q9HAS3 Link_out
      Gene: SLC28A3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Badagnani I, Chan W, Castro RA, Brett CM, Huang CC, Stryke D, Kawamoto M, Johns SJ, Ferrin TE, Carlson EJ, Burchard EG, Giacomini KM: Functional analysis of genetic variants in the human concentrative nucleoside transporter 3 (CNT3; SLC28A3). Pharmacogenomics J. 2005;5(3):157-65. Pubmed
      Comments
      Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19