ADN

ADENOSINE

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

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209 entries where ADN is found as a standalone ligand4 entries where ADN is covalently linked to polymer or other heterogen groups 2 entries where ADN is found in a polymer sequence

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	4
Bond Count	34
Aromatic Bond Count	10

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Chemical Component Summary
Name	ADENOSINE
Systematic Name (OpenEye OEToolkits)	(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Formula	C₁₀ H₁₃ N₅ O₄
Molecular Weight	267.241
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	n2c1c(ncnc1n(c2)C3OC(C(O)C3O)CO)N
SMILES	CACTVS	3.341	Nc1ncnc2n(cnc12)[CH]3O[CH](CO)[CH](O)[CH]3O
SMILES	OpenEye OEToolkits	1.5.0	c1nc(c2c(n1)n(cn2)C3C(C(C(O3)CO)O)O)N
Canonical SMILES	CACTVS	3.341	Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
InChI	InChI	1.03	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
InChIKey	InChI	1.03	OIRDTQYFTABQOQ-KQYNXXCUSA-N

Drug Info: DrugBank

DrugBank ID	DB00640
Name	Adenosine
Groups	approved investigational
Description	The 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thallium-201 in myocardial perfusion scintigraphy,[L31983] though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson].[A229833,A229838] Adenosine is also indicated in the treatment of supraventricular tachycardia.[L31998] Adenosine was granted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-beta-D-Ribofuranosyl-9H-purin-6-amine 9-beta-D-Ribofuranosidoadenine (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol beta-D-Adenosine Ado Adénosine Adenine Deoxyribonucleoside Adenosina 9-β-D-ribofuranosyl-9H-purin-6-amine 6-Amino-9-beta-D-ribofuranosyl-9H-purine Adenosine Ade-Rib Adenosinum Adenogesic Adenosin Adenin riboside
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Indication	Adenosine 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 Antiarrhythmics, Class V Biological Factors Carbohydrates Cardiac Therapy Cardiovascular Agents Central Nervous System Agents Cyclohexanes Cyclohexenes Cycloparaffins Glycosides Heterocyclic Compounds, Fused-Ring Hydrocarbons, Acyclic Miscellaneous Cardiac Drugs Miscellaneous Therapeutic Agents Moderate Risk QTc-Prolonging Agents Neurotransmitter Agents Nucleic Acids, Nucleotides, and Nucleosides Nucleosides Peripheral Nervous System Agents Polyenes Purine Nucleosides Purinergic Agents Purinergic Agonists Purinergic P1 Receptor Agonists Purines QTc Prolonging Agents Ribonucleosides Sensory System Agents Terpenes Vasodilating Agents
ATC-Code	C01EB10
CAS number	58-61-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Adenosine receptor A1	MPPSISAFQAAYIGIEVLIALVSVPGNVLVIWAVKVNQALRDATFCFIVS...	unknown	agonist
Adenosine receptor A2a	MPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...	unknown	agonist
Adenosine receptor A2b	MLLETQDALYVALELVIAALSVAGNVLVCAAVGTANTLQTPTNYFLVSLA...	unknown	agonist
Adenosine receptor A3	MPNNSTALSLANVTYITMEIFIGLCAIVGNVLVICVVKLNPSLQTTTFYF...	unknown	agonist
Adenylate kinase isoenzyme 1	MEEKLKKTKIIFVVGGPGSGKGTQCEKIVQKYGYTHLSTGDLLRSEVSSG...	unknown	substrate
Nucleoside diphosphate kinase A	MANCERTFIAIKPDGVQRGLVGEIIKRFEQKGFRLVGLKFMQASEDLLKE...	unknown	substrate
Nucleoside diphosphate kinase B	MANLERTFIAIKPDGVQRGLVGEIIKRFEQKGFRLVAMKFLRASEEHLKQ...	unknown	substrate
Purine nucleoside phosphorylase	MENGYTYEDYKNTAEWLLSHTKHRPQVAIICGSGLGGLTDKLTQAQIFDY...	unknown	substrate
Xanthine dehydrogenase/oxidase	MTADKLVFFVNGRKVVEKNADPETTLLAYLRRKLGLSGTKLGCGEGGCGA...	unknown	substrate
Adenosine deaminase	MAQTPAFDKPKVELHVHLDGSIKPETILYYGRRRGIALPANTAEGLLNVI...	unknown	substrate
Adenosine kinase	MAAAEEEPKPKKLKVEAPQALRENILFGMGNPLLDISAVVDKDFLDKYSL...	unknown	substrate
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Equilibrative nucleoside transporter 1	MTTSHQPQDRYKAVWLIFFMLGLGTLLPWNFFMTATQYFTNRLDMSQNVS...	unknown	substrate
Equilibrative nucleoside transporter 2	MARGDAPRDSYHLVGISFFILGLGTLLPWNFFITAIPYFQARLAGAGNST...	unknown	substrate
Equilibrative nucleoside transporter 3	MAVVSEDDFQHSSNSTYRTTSSSLRADQEALLEKLLDRPPPGLQRPEDRF...	unknown	substrate
Equilibrative nucleoside transporter 4	MGSVGSQRLEEPSVAGTPDPGVVMSFTFDSHQLEEAAEAAQGQGLRARGV...	unknown	substrate
Sodium/nucleoside cotransporter 1	MENDPSRRRESISLTPVAKGLENMGADFLESLEEGQLPRSDLSPAEIRSS...	unknown	substrate
Sodium/nucleoside cotransporter 2	MEKASGRQSIALSTVETGTVNPGLELMEKEVEPEGSKRTDAQGHSLGDGL...	unknown	substrate
Gap junction alpha-1 protein	MGDWSALGKLLDKVQAYSTAGGKVWLSVLFIFRILLLGTAVESAWGDEQS...	unknown	substrate
Solute carrier family 28 member 3	MELRSTAAPRAEGYSNVGFQNEENFLENENTSGNNSIRSRAVQSREHTNT...	unknown
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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