ADN

ADENOSINE

Created:1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count4
Bond Count34
Aromatic Bond Count10
2D diagram of ADN
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Chemical Component Summary

NameADENOSINE
Systematic Name (OpenEye OEToolkits)(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
FormulaC10 H13 N5 O4
Molecular Weight267.241
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04n2c1c(ncnc1n(c2)C3OC(C(O)C3O)CO)N
SMILESCACTVS3.341Nc1ncnc2n(cnc12)[CH]3O[CH](CO)[CH](O)[CH]3O
SMILESOpenEye OEToolkits1.5.0c1nc(c2c(n1)n(cn2)C3C(C(C(O3)CO)O)O)N
Canonical SMILESCACTVS3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
Canonical SMILESOpenEye OEToolkits1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
InChIInChI1.03 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
InChIKeyInChI1.03 OIRDTQYFTABQOQ-KQYNXXCUSA-N

Drug Info: DrugBank

DrugBank IDDB00640 
NameAdenosine
Groups
  • approved
  • investigational
DescriptionThe structure of adenosine was first described in 1931,[A229823] though the vasodilating effects were not described in literature until the 1940s.[A229828] Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy,[L31983] though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson].[A229833,A229838] Adenosine is also indicated in the treatment of supraventricular tachycardia.[L31998] Adenosine was granted FDA approval on 30 October 1989.[L31978]
Synonyms
  • 9-β-D-ribofuranosyl-9H-purin-6-amine
  • 6-Amino-9-beta-D-ribofuranosyl-9H-purine
  • Adenogesic
  • 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  • Adenosina
Brand Names
  • Celonia Signature Bio Essence Toner
  • COMPLETE CHOICE Moisture Amploule
  • Medi Hydro DP Cream
  • Forestheal Eye
  • Snail Solu Tion Skin Booster
IndicationAdenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy in patients unable to adequately exercise.[L31983] It is also indicated to convert sinus rhythm of paroxysmal supraventricular tachycardia.[L31998]
Categories
  • Adenosine, antagonists & inhibitors
  • Agents producing tachycardia
  • Alkenes
  • Analgesics
  • Antiarrhythmic agents
ATC-CodeC01EB10
CAS number58-61-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Adenosine receptor A1MPPSISAFQAAYIGIEVLIALVSVPGNVLVIWAVKVNQALRDATFCFIVS...unknownagonist
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownagonist
Adenosine receptor A2bMLLETQDALYVALELVIAALSVAGNVLVCAAVGTANTLQTPTNYFLVSLA...unknownagonist
Adenosine receptor A3MPNNSTALSLANVTYITMEIFIGLCAIVGNVLVICVVKLNPSLQTTTFYF...unknownagonist
Adenylate kinase isoenzyme 1MEEKLKKTKIIFVVGGPGSGKGTQCEKIVQKYGYTHLSTGDLLRSEVSSG...unknownsubstrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL477
PubChem 60961
ChEMBL CHEMBL477
ChEBI CHEBI:16335
CCDC/CSD ADENOS10, CATGOV, CATGUB, CATGIP, DOHSIC, ADOSBU01, ADENOS13