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Adenosine

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Adenosine Basic information
Physiological function Vidarabine Chemical Properties Uses Category Toxicity grading Acute toxicity Flammability hazard characteristics Storage and transportation characteristics Extinguishing agent
Product Name:Adenosine
Synonyms:D-ADENOSINE;AR;(2R,3R,4S,5R)-2-(6-AMINO-PURIN-9-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL;9-BETA-D-RIBOFURANOSYLADENINE;ADENINENUCLEOSIDE;ADENINE RIBOSIDE;ADENOSINE;ADENINE-9-BETA-D-RIBOFURANOSIDE
CAS:58-61-7
MF:C10H13N5O4
MW:267.24
EINECS:200-389-9
Product Categories:Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Purine;API intermediates;Nucleosides and their analogs;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;sy;ADENOCARD;nucleoside;Antiarrhythmic;API;Inhibitors
Mol File:58-61-7.mol
Adenosine Structure
Adenosine Chemical Properties
mp 234-236 °C(lit.)
storage temp. 2-8°C
Merck 14,153
BRN 93029
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference58-61-7(CAS DataBase Reference)
NIST Chemistry Referenceadenosine(58-61-7)
Safety Information
Safety Statements 24/25
WGK Germany 2
RTECS AU7175000
10-23
MSDS Information
ProviderLanguage
Adenosine English
SigmaAldrich English
ACROS English
ALFA English
Adenosine Usage And Synthesis
Physiological functionAdenosine is the active substance with the basic structure of the nucleoside and purine, which is a kind of nucleoside formed by adenine through beta glyosidic bond with D-ribose. It widely exists in all types of cells, which can be in the form of free or with the combination of nucleosides in nucleic acids. Adenosine phosphate, like ATP, is an important energy carrier in biochemical reactions.
Adenosine is a natural nucleotide, which is the intermediate product of metabolism, and is also one of the important active components in the body. Its 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 is an inhibitory neuromodulator in the central nervous system, which can provide a signal between the brain's energy storage and energy requirements, so as to achieve a balance. Under normal conditions, the extracellular adenosine concentration was maintained at 40 ~ 400nmoL.During ischemia and hypoxia, Glucose and glycogen are accelerated decomposition to produce ATP in response to energy demand; ATP degrade, so that the level of intracellular adenosine increases dramatically, and then is released to the outside of the cells to play its regulatory role. In the recovery phase of hypoxia, endogenous adenosine is the precursor of ATP synthesis, and ATP can be re generated under the action of adenosine kinase (AK) in order to prolong the survival time of the cells.
Adenosine has a role in the expansion of coronary artery and myocardial contractility .Clinical application in the treatment of angina, hypertension, cerebrovascular disorders, stroke sequelae, muscular atrophy, etc. Intravenous injection for the treatment of ventricular tachycardia and 201Tl myocardial imaging.
The above information is edited by the chemicalbook of Tian Ye.
VidarabineVidarabine is a kind of artificial synthetic antitumor compounds, which belongs to adenosine derivatives, extracted from actinomyces fermentation liquid, with a broad spectrum of anti-herpes virus and anti-hepadna virus effect .After entering the infected cells it generates a biologically active triphosphate vidarabine. Interfering with viral DNA synthesis for broad-spectrum antiviral.It can be quickly into the cells through intravenous administration and the concentration of kidney, liver, spleen is high; the concentration in cerebrospinal fluid is 1/3 of blood concentration. The product has an significant inhibitory effect on herpes virus, adenovirus, chicken pox virus, hepatitis B virus and so on, but the RNA virus is invalid. Compared with similar products idoxuridine, vidarabine is more effective on deep infection of DNA viruses or recurrent infection, which has lower toxicity and weaker effect than Arabinoside.
Vidarabine has broad-spectrum anti-viral DNA effects in tissue culture to suppress herpes simplex virus Ⅰ, Ⅱ type, chicken pox----Zoster virus, cytomegalovirus, E-B virus, pox virus, and pseudorabies virus. Triphosphate adenosine can inhibit herpes simplex and hepatitis B virus DNA polymerase. It has no cross resistance with other types of anti-herpes drugs. Animal experiments show that it has effective for the herpes simplex virus keratitis and the herpes simplex virus and the pox virus encephalitis in rabbits, but the effect on the infection of guinea pig skin herpes virus is bad, and it is effective for chimpanzee and human hepatitis B virus infection. Adenosine has less toxicity, but large dose has teratogenic and mutagenic side effects. Vidarabine mechanism has not been fully elucidated, mainly phosphorylated to vidarabine triphosphate in intracellular, inhibited viral DNA polymerase, whose inhibition of DNA polymerase is weak, thus selectively inhibit the synthesis and replication of viral DNA.
Chemical PropertiesCrystallization from water, Melting point: 234--235℃. [α]D11-61.7°(C=0.706,water);[α] D9-58.2°(C=0.658,water).Insoluble in alcohol.
UsesAnti-arrhythmia drugs, it can make paroxysmal ventricular tachycardia into sinus rhythm. Used for ventricular arrhythmias associated with atrioventricular.
Antiviral drugs.
In the pharmaceutical industry, it is mainly used for the manufacture of the main raw materials of the drugs, such as adenosine triphosphate, coenzyme and its series products such as cyclic adenosine monophosphate and so on.
For the manufacture of ATP, adenosine, coenzyme A, etc.
Treatment of angina pectoris, myocardial infarction, coronary insufficiency, atherosclerosis, hypertension, cerebrovascular disease, stroke sequelae, progressive muscular atrophy. Atrioventricular block and acute myocardial infarction patients disabled.
CategoryToxic Substances
Toxicity gradingModerately toxic
Acute toxicityPeritoneal - mouse LD50: 500 mg / kg
Flammability hazard characteristicsCombustible; combustion releases toxic nitrogen oxide smoke.
Storage and transportation characteristicsTreasury ventilation low-temperature drying; and food raw materials stored separately.
Extinguishing agentDry powder, foam, sand, carbon dioxide, water mist.
Chemical PropertiesWhite crystalline powder
Usageantiarrhythmic, cardiac depressant
UsageNucleotide.
Biological ActivityNeurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.
Adenosine Preparation Products And Raw materials
Preparation ProductsVidarabine-->Calcium 5'-ribonucleotide
Tag:Adenosine(58-61-7) Related Product Information
Adenosine 5'-triphosphate disodium salt Cytidine ADENOSINE 2',5'-DIPHOSPHATE SODIUM SALT [1'-13C]ADENOSINE Adenosine 6-Chloropurine riboside Adenine hydrochloride hemihydrate Benzyladenine 1-BETA-D-RIBOFURANOSE Adenosine 5'-triphosphate disodium salt (2R,3S,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol 1H-Purin-6-amine sulfate ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE,ADENOSINE 3'-,5'-CYCLIC MONOPHOSPHATE,(-)-ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE Adenine Adenine phosphate PUROMYCIN AMINONUCLEOSIDE 5'-Guanylic acid Guanosine