<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4329</id>
  <title>T3D4275</title>
  <common-name>Adenosine</common-name>
  <description>Adenosine is 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. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent.</description>
  <cas>58-61-7</cas>
  <pubchem-id>60961</pubchem-id>
  <chemical-formula>C10H13N5O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>235.5°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>8230 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>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 A&lt;sub&gt;1&lt;/sub&gt; and A&lt;sub&gt;2&lt;/sub&gt; 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.</mechanism-of-toxicity>
  <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.Half Life: Less than 10 secs</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>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.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Chronically high levels of adeonsine are associated with Adenosine Deaminase Deficiency.</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:11:54Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:44:49Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Adenosine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00212</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>16335</chebi-id>
  <biocyc-id>ADENOSINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00640</drugbank-id>
  <pdb-id>ADN</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1</moldb-smiles>
  <moldb-formula>C10H13N5O4</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>OIRDTQYFTABQOQ-KQYNXXCUSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">267.2413</moldb-average-mass>
  <moldb-mono-mass type="decimal">267.096753929</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-1.05</logp>
  <hmdb-id>HMDB00050</hmdb-id>
  <chembl-id>CHEMBL477</chembl-id>
  <chemspider-id>54923</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Giorgio Stramentinoli, Federico Gennari, &amp;#8220;Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity.&amp;#8221; U.S. Patent US4373097, issued October, 1965.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003235</chemdb-id>
  <dsstox-id>DTXSID1022558</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00098759</susdat-id>
  <iupac>(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol</iupac>
  <moldb-polar-surface-area>139.54</moldb-polar-surface-area>
  <moldb-refractivity>63.1956</moldb-refractivity>
  <moldb-polarizability>25.28306076008305</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.45400327595609</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>3.921276940416587</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>-1.21</moldb-alogps-logp>
  <moldb-alogps-logs>-1.28</moldb-alogps-logs>
  <moldb-alogps-solubility>1.40e+01 g/l</moldb-alogps-solubility>
</compound>
