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Adenosine

Catalog No. DB00640 Name DrugBank
CAS Number 58-61-7 Website http://www.ualberta.ca/
M. F. C10H13N5O4 Telephone (780) 492-3111
M. W. 267.24132 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 522

SYNONYMS

IUPAC name
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
IUPAC Traditional name
adenosine
Brand Name
Pallacor
Adenocard
Myocol
Adenoscan
Adenosin
Nucleocardyl
Sandesin
Adenocor
Adensoine
Boniton
Synonyms
Adenine Deoxy Nucleoside
Adenyldeoxyriboside
Adenine Deoxyribose
Adenine Riboside
Deoxyadenosine
Desoxyadenosine
USAF CB-10
MEDR-640
2'-Deoxyadenosine
Adenine Deoxyribonucleoside
Adenine Nucleoside
adenosine

DATABASE IDS

CAS Number 58-61-7
PubChem SID 46508728
PubChem CID 60961

PROPERTIES

Hydrophobicity(logP) -1.6
Solubility 8230 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved; 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]
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.
Pharmacology 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.
Affected Organisms
Humans and other mammals
Biotransformation 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
External Links
Wikipedia
RxList
Drugs.com

REFERENCES