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Adenosine

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Adenosine Basic information
Defination In the body Medical uses Mechanism of action
Product Name:Adenosine
Synonyms:D-ADENOSINE;(2R,3R,4S,5R)-2-(6-AMINO-PURIN-9-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL;9-BETA-D-RIBOFURANOSYLADENINE;Adenine riboside, Adenine-9-beta-ribofuranoside;ADENOSINE extrapure for biochemistry;ADENINE RIBOSIDE;ADENOSINE;ADENINE-9-BETA-D-RIBOFURANOSIDE
CAS:58-61-7
MF:C10H13N5O4
MW:267.24
EINECS:200-389-9
Product Categories:ADENOCARD;nucleoside;Bases & Related Reagents;sy;Antiarrhythmic;API;Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Purine;API intermediates;Nucleosides and their analogs;Nucleic acids;Nucleotides;Inhibitors;Biochemistry;Nucleosides, Nucleotides & Related Reagents;58-61-7
Mol File:58-61-7.mol
Adenosine Structure
Adenosine Chemical Properties
Melting point 234-236 °C (lit.)
Boiling point 410.43°C (rough estimate)
alpha D11 -61.7° (c = 0.706 in water); 9D -58.2° (c = 0.658 in water)
density 1.3382 (rough estimate)
refractive index 1.7610 (estimate)
storage temp. 2-8°C
solubility Slightly soluble in water, soluble in hot water, practically insoluble in ethanol (96 per cent) and in methylene chloride. It dissolves in dilute mineral acids.
form Crystalline Powder
pka3.6, 12.4(at 25℃)
color White
optical activity[α]20/D 70±3°, c = 2% in 5% NaOH
Water Solubility Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol.
Merck 14,153
BRN 93029
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
CAS DataBase Reference58-61-7(CAS DataBase Reference)
NIST Chemistry Referenceadenosine(58-61-7)
EPA Substance Registry SystemAdenosine (58-61-7)
Safety Information
Risk Statements 36/37/38
Safety Statements 24/25-36/37/39-26
WGK Germany 2
RTECS AU7175000
10-23
TSCA Yes
HS Code 29389090
Hazardous Substances Data58-61-7(Hazardous Substances Data)
ToxicityLD50 oral in mouse: > 20gm/kg
MSDS Information
ProviderLanguage
Adenosine English
SigmaAldrich English
ACROS English
ALFA English
Adenosine Usage And Synthesis
DefinationAdenosine is a natural nucleotide, which is the intermediate product of metabolism, chemically 6-amino-9-beta-D-ribofuranosyl-9-H-purine. Adenosine is one of the important active components in the body, helps in cellular energy transfer by forming molecules like adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signaling various pathways and functions in the body by forming signally molecules like cyclic adenosine monophosphate (cAMP).
In the body
Adenosine in the body
Function
Brain
Promoting sleep and suppresses arousal acting as a central nervous system depressant.
Heart
Causing dilation of the coronary blood vessels that Improving blood circulation to the heart; Increasing the diameter of blood vessels in the peripheral organs; Decreasing heart rate
Blood
Broken down by adenosine deaminase. By taking medicine like Dipyridamole(inhibitor of adenosine deaminase), it can improve blood flow through the coronary blood vessels that supply the heart muscles.
Kidneys, lungs and liver
In the kidneys adenosine decreases renal blood flow and decrease the production of rennin from the kidneys. In the lungs it causes constriction of airways and in the liver it leads to constriction of blood vessels and increases breakdown of glycogen to form glucose.
Medical usesAdenosine has a role in the expansion of coronary artery and myocardial contractility, is clinically applied in the treatment of angina, hypertension, cerebrovascular disorders, stroke sequelae, muscular atrophy, etc. It is also given intravenously (by IV) for treating supraventricular tachycardia and Tl myocardial imaging. It is also used for cardiac stress tests.   Side effects:
Since the half-life of this compound is less than 10 seconds, its side effects are usually transient. However, side effects are common, and include flushing, headache, chest discomfort, bronchoconstriction, and occasionally hypotension. Hepatic and renal failure and other drugs except dipyridamole seem to have little effect on the action of adenosine.     Adenosine dose

   
Mechanism of actionIts function is realized through the activation of the adenosine receptor (A receptor). Adenosine activates G protein coupled potassium channels by binding to the A receptor which makes increasing the outflow of K+ and cell membrane hyperpolarization so as to decrease the automaticity in the atrium, sinoatrial node and atrioventricular node. It can also significantly increase the level of cGMP , prolong ERP of the atrioventricular node and slowing of atrioventricular, depress sympathetic nervous or early and delayed after depolarization induced by isoproterenol and then plays an effective role in arrhythmia. This product has not been classified in I~IV anti arrhythmia medicine.

Adenosine receptor
  • A1 receptors, which are found in cardiomyocytes and which are responsible for the inhibition of adenylyl cylase activity which lowers cyclic adenosine monophosphate (AMP) results in sinus slowing, increase in AV node conduction delay, and antagonism of the effects of catecholamines;
  • A2 receptors, which are found in endothelial cells and vascular smooth muscle and are responsible for the enhancement of adenylyl cylase activity and increased cyclic AMP which relaxes smooth muscle. Both negative chronotropic and dromotropic effects of adenosine are cyclic AMP independent (direct action) as well cyclic AMP dependent (indirect action).
DescriptionAdenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond. Adenosine works in the energy transfer-as adenosine triphosphate (ATP) and adenosine diphosphate (ADP)-as well as in signal transduction as cyclic adenosine monophosphate, cAMP. It shows neuromodulatory, cytoprotective, anti-inflammatory and cardioprotective actions.
Chemical PropertiesWhite or almost white, crystalline powder.
Chemical PropertiesAdenosine is an important nucleoside composed of adenine and ribose. White, crystalline, odorless powder, mild, saline, or bitter taste, quite soluble in hot water, practically insoluble in alcohol. Formed by isolation following hydrolysis of yeast nucleic acid.
UsesNucleotide.
Usesantiarrhythmic, cardiac depressant
Usesadenosine is an amino acid. Studies indicate anti-wrinkle and skinsmoothing capacities. Although little is written about its direct skin benefit, adenosine plays an important role in biochemical processes. As adenosine triphosphate (ATP) and adenosine diphosphate (ADP), it is involved in energy transfer, and as cyclic adenosine monophosphate (cAMP) in signal transduction.
Definitionadenosine: A nucleoside comprisingone adenine molecule linked to ad-ribose sugar molecule. The phosphate-ester derivatives of adenosine,AMP, ADP, and ATP, are of fundamentalbiological importance as carriersof chemical energy.
DefinitionChEBI: A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta1N9-glycosidic bond.
Brand nameAdenocard (Astellas); Adenoscan (Astellas).
General DescriptionAdenosine is a purine nucleoside and a building block of RNA and many other biomolecules such as adenosine triphosphate and nicotinamide adenine dinucleotide. In the extracellular space, ecto-5′-nucleotidase (CD73) dephosphorylates adenosine triphosphate (ATP) to produce adenosine. Adenosine has four receptors namely A1R, A2AR A2BR and A3R. Adenosine plays a key role in the osteogenic differentiation. A1R induces osteoclast differentiation and A2AR induces osteoblast differentiation.
Biological ActivityNeurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.
Biochem/physiol ActionsEndogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti?inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).
Clinical UseAdenosine (Adenocard) is an endogenous nucleoside that is a product of the metabolism of adenosine triphosphate. It is used for the rapid termination of supraventricular arrhythmias following rapid bolus dosing.
Adenosine is approved for the acute management and termination of supraventricular tachyarrhythmias, including A-V nodal reentrant tachycardia and A-V reciprocating tachycardia. Adenosine may be helpful in the diagnosis of atrial flutter.
Side effectsAdverse reactions to the administration of adenosine are fairly common; however, the short half-life of the drug limits the duration of such events.The most common adverse effects are flushing, chest pain, and dyspnea. Adenosine may induce profound bronchospasm in patients with known reactive airway disease. The mechanism for bronchospasm is unclear, and the effect may last for up to 30 minutes despite the short half-life of the drug.
Drug interactionsMetabolism of adenosine is slowed by dipyridamole, indicating that in patients stabilized on dipyridamole the therapeutically effective dose of adenosine may have to be increased. Methylxanthines antagonize the effects of adenosine via blockade of the adenosine receptors.
MetabolismIt is impossible to study adenosine in classical pharmacokinetic studies, since it is present in various forms in all the cells of the body. An efficient salvage and recycling system exists in the body, primarily in erythrocytes and blood vessel endothelial cells. The halflife in vitro is estimated to be less than 10 seconds, and may be even shorter in vivo.
Purification MethodsCrystallise adenosine from distilled water and dry it at 110o. It has been purified via the picrate, where ethanolic picric acid is added to adenosine and the picrate is filtered off and recrystallised from EtOH. It has m 180-185o(dec). Adenosine is recovered by dissolving 0.4g of the picrate in 80mL of hot H2O, treated with a small quantity of Dowex 1 anion exchange resin in the chloride form, and the resin is filtered off. The filtrate is treated with more resin and filtered again. One equivalent of aqueous NaOH is added to the colourless filtrate which is evaporated to 4mL and cooled to give 0.176g of adenosine m 236o. [Davoll et al. J Chem Soc 967 1948, Davoll & Lowy J Am Chem Soc 73 1650 1951, Beilstein 26 III/IV 3598.]
PrecautionsPatients with second- or third-degree A-V block should not receive adenosine. As indicated previously, the use of adenosine in asthmatic patients may exacerbate the asthmatic symptoms.
Tag:Adenosine(58-61-7) Related Product Information
S-Adenosyl-L-methionine ADENOSINE-5'-DIPHOSPHOGLUCOSE Adenine phosphate salt(1:1) Adenine hydrochloride hemihydrate Adenosine 5’-triphosphate disodium salt Adenosine triphosphate Adenine hydrochloride Cytidine Adenine Adenosine 5'-monophosphate Adenosine-5'-diphosphate disodium salt Adenosine-5'-diphosphate trilithium salt BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT ADENOSINE-2,8-3H 5'-MONOPHOSPHATE DIAMMONIUM SALT ADENOSINE-13C10,15N5 5'-TRIPHOSPHATE SODIUM SALT ADENOSINE-2',5'-BISPHOSPHATE TRIETHYLAMMONIUM SALT ADENOSINE-2,8-3H 5'-TRIPHOSPHATE TETRAAMMONIUM SALT ADENOSINE-2',3'-DIALDEHYDE