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Identification
NameAdenosine
Accession NumberDB00640  (APRD00132)
Typesmall molecule
Groupsapproved, investigational
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
Synonyms
SynonymLanguageCode
Adenin ribosideNot AvailableIS
AdenosinGermanINN
AdenosinaSpanishINN
AdénosineFrenchINN
AdenosinumLatinINN
AdoNot AvailableIS
SaltsNot Available
Brand names
NameCompany
AdenocardAstellas
AdenocorSanofi-Aventis
AdenojectSun
AdénoscanSanofi-Aventis
AdenoscanAstellas
AdenozCelon
AdenozerPurzer
AdesinDae Han New Pharm
AdrekarSanofi-Aventis
AtépadèneMayoly-Spindler
CardimaxAC Farma
CardiovertSanofi-Aventis
KrenosinSanofi-Aventis
OsidenSquare
PisdenoPisa
TricorSanofi-Aventis
Brand mixturesNot Available
Categories
CAS number58-61-7
WeightAverage: 267.2413
Monoisotopic: 267.096753929
Chemical FormulaC10H13N5O4
InChI KeyInChIKey=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
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
Mass Specshow(9.12 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPurine Nucleosides and Analogues
Alternative parentsPentoses; Purines and Purine Derivatives; Aminopyrimidines and Derivatives; N-substituted Imidazoles; Primary Aromatic Amines; Tetrahydrofurans; Oxolanes; Secondary Alcohols; 1,2-Diols; Ethers; Primary Alcohols; Polyamines
Substituentspentose monosaccharide; imidazopyrimidine; purine; aminopyrimidine; primary aromatic amine; pyrimidine; monosaccharide; n-substituted imidazole; tetrahydrofuran; imidazole; azole; oxolane; secondary alcohol; 1,2-diol; polyamine; primary alcohol; ether; organonitrogen compound; primary amine; alcohol; amine
Classification descriptionThis compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar.
Pharmacology
IndicationUsed 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.
PharmacodynamicsAdenosine 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 actionAdenosine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot 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.

SubstrateEnzymesProduct
Adenosine
    Adenosine monophosphateDetails
    Adenosine
      InosineDetails
      Route of eliminationNot Available
      Half lifeLess than 10 secs
      ClearanceNot Available
      ToxicityNot Available
      Affected organisms
      • Humans and other mammals
      Pathways
      PathwayCategorySMPDB ID
      Intracellular Signalling Through Adenosine Receptor A2a and AdenosineSignalingSMP00320
      Intracellular Signalling Through Adenosine Receptor A2b and AdenosineSignalingSMP00321
      Selenoamino Acid MetabolismMetabolicSMP00029
      Thioguanine Action PathwayDrug actionSMP00430
      Azathioprine Action PathwayDrug actionSMP00427
      Mercaptopurine Action PathwayDrug actionSMP00428
      Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
      Adenosine Deaminase DeficiencyDiseaseSMP00144
      S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDiseaseSMP00214
      Methionine Adenosyltransferase DeficiencyDiseaseSMP00221
      Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
      AICA-RibosiduriaDiseaseSMP00168
      Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDiseaseSMP00570
      Cystathionine Beta-Synthase DeficiencyDiseaseSMP00177
      Betaine MetabolismMetabolicSMP00123
      Molybdenium Cofactor DeficiencyDiseaseSMP00203
      Myoadenylate deaminase deficiencyDiseaseSMP00537
      Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)DiseaseSMP00340
      Glycine N-methyltransferase DeficiencyDiseaseSMP00222
      Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
      Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
      Mitochondrial DNA depletion syndromeDiseaseSMP00536
      Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
      HypermethioninemiaDiseaseSMP00341
      Xanthinuria type IDiseaseSMP00512
      Xanthinuria type IIDiseaseSMP00513
      Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
      Purine MetabolismMetabolicSMP00050
      Methionine MetabolismMetabolicSMP00033
      SNP Mediated EffectsNot Available
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      Predicted ADMET features
      Property Value Probability
      Human Intestinal Absorption + 0.9227
      Blood Brain Barrier + 0.9383
      Caco-2 permeable - 0.8957
      P-glycoprotein substrate Non-substrate 0.7026
      P-glycoprotein inhibitor I Non-inhibitor 0.966
      P-glycoprotein inhibitor II Non-inhibitor 0.9533
      Renal organic cation transporter Non-inhibitor 0.9444
      CYP450 2C9 substrate Non-substrate 0.8639
      CYP450 2D6 substrate Non-substrate 0.8349
      CYP450 3A4 substrate Non-substrate 0.5866
      CYP450 1A2 substrate Non-inhibitor 0.9667
      CYP450 2C9 substrate Non-inhibitor 0.9595
      CYP450 2D6 substrate Non-inhibitor 0.977
      CYP450 2C19 substrate Non-inhibitor 0.9514
      CYP450 3A4 substrate Non-inhibitor 0.962
      CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9701
      Ames test Non AMES toxic 0.9133
      Carcinogenicity Non-carcinogens 0.9182
      Biodegradation Not ready biodegradable 0.9738
      Rat acute toxicity 1.9715 LD50, mol/kg Not applicable
      hERG inhibition (predictor I) Weak inhibitor 0.989
      hERG inhibition (predictor II) Non-inhibitor 0.9102
      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
      FormRouteStrength
      LiquidIntravenous
      SolutionIntravenous
      Prices
      Unit descriptionCostUnit
      Adenosine-5 monophosphate19.74USDg
      Adenosine powder15.86USDg
      Adenoscan 3 mg/ml vial10.09USDml
      Adenosine 12 mg/4 ml vial8.44USDml
      Adenosine 6 mg/2 ml vial8.1USDml
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents
      CountryPatent NumberApprovedExpires (estimated)
      United States57312961995-03-242015-03-24
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      melting point235.5 °CPhysProp
      water solubility8230 mg/LNot Available
      logP-1.05HANSCH,C ET AL. (1995)
      Predicted Properties
      PropertyValueSource
      water solubility1.40e+01 g/lALOGPS
      logP-1.2ALOGPS
      logP-2.1ChemAxon
      logS-1.3ALOGPS
      pKa (strongest acidic)12.45ChemAxon
      pKa (strongest basic)4.99ChemAxon
      physiological charge0ChemAxon
      hydrogen acceptor count8ChemAxon
      hydrogen donor count4ChemAxon
      polar surface area139.54ChemAxon
      rotatable bond count2ChemAxon
      refractivity63.2ChemAxon
      polarizability25.27ChemAxon
      number of rings3ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterNoChemAxon
      Veber's ruleNoChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      Spectra
      References
      Synthesis Reference

      Giorgio Stramentinoli, Federico Gennari, “Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity.” U.S. Patent US4373097, issued October, 1965.

      US4373097
      General ReferenceNot Available
      External Links
      ResourceLink
      KEGG DrugD00045
      KEGG CompoundC00212
      PubChem Compound60961
      PubChem Substance46508728
      ChemSpider54923
      ChEBI16335
      ChEMBLCHEMBL477
      Therapeutic Targets DatabaseDAP000223
      PharmGKBPA448049
      HET101
      Drug Product Database2243435
      RxListhttp://www.rxlist.com/cgi/generic3/adenos.htm
      Drugs.comhttp://www.drugs.com/cdi/adenosine.html
      WikipediaAdenosine
      ATC CodesC01EB10
      AHFS Codes
      • 92:00.00
      PDB EntriesNot Available
      FDA labelshow(154 KB)
      MSDSshow(72.7 KB)
      Interactions
      Drug Interactions
      Drug
      AminophyllineThis xanthine decreases the effect of adenosine
      CaffeineCaffeine 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.
      DipyridamoleDipyridamole may increase the effect/toxicity of adenosine.
      DyphyllineThis xanthine decreases the effect of adenosine
      OxtriphyllineThis xanthine decreases the effect of adenosine
      TheophyllineTheophylline may decrease the effect of adenosine.
      Food Interactions
      • Avoid caffeine containing foods and drinks.

      1. Adenosine receptor A2a

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      Adenosine receptor A2a P29274 Details

      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 receptor A2b

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      Adenosine receptor A2b P29275 Details

      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 receptor A3

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      Adenosine receptor A3 P33765 Details

      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 receptor A1

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      Adenosine receptor A1 P30542 Details

      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

      1. Adenosine deaminase

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Adenosine deaminase P00813 Details

      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

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Adenosine kinase P55263 Details

      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

      1. Solute carrier family 28 member 3

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Components

      Name UniProt ID Details
      Solute carrier family 28 member 3 Q9HAS3 Details

      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 September 16, 2013 17:11