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REGADENOSON

REGADENOSON Structure
REGADENOSON
  • CAS No.313348-27-5
  • Chemical Name:REGADENOSON
  • CBNumber:CB0501002
  • Molecular Formula:C15H18N8O5
  • Formula Weight:390.35
  • MOL File:313348-27-5.mol
REGADENOSON Property
  • Melting point 158-160°C
  • Density 1.98±0.1 g/cm3(Predicted)
  • storage temp. Keep in dark place,Sealed in dry,2-8°C
  • solubility DMSO (Slightly), Methanol (Slightly, Sonicated)
  • form Solid
  • pka 13.07±0.70(Predicted)
  • color Off-White to Pale Brown
  • CAS DataBase Reference 313348-27-5
  • FDA UNII 7AXV542LZ4
  • NCI Drug Dictionary regadenoson
  • ATC code C01EB21
  • UNSPSC Code 12352211
  • NACRES NA.77
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300-H330-H310
  • Precautionary statements P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501

REGADENOSON Chemical Properties,Usage,Production

  • Description Lexiscan ™(regadenoson) is an injectable adenosine A2A receptor agonist for use as a pharmacologic stress agent in myocardial perfusion imaging (MPI) studies in patients unable to undergo adequate exercise induced stress. Regadenoson is the first adenosine A2A receptor agonist shown to be safe and effective as a pharmacologic stress agent in MPI studies. It is delivered as a rapid bolus (approximately 10 seconds) with no dose adjustment required for body weight. The product was developed under a license and collaboration agreement between CV Therapeutics and Astellas, and was launched by Astellas in June of 2008.
  • Chemical Properties Off-White Solid
  • Uses Regadenoson is a selective, short-acting adenosine A2A receptor agonist (Ki = 1.1 nM for pig striatum A2A receptor). It increases coronary blood flow 3.4- to 3.8-fold with a half-time to reversal of 1.9-2.6 minutes in open-chest anesthetized pigs. Regadenoson is used to induce hyperemia (increased blood flow), particularly in the context of myocardial perfusion imaging. It has also been found to increase the delivery of compounds to the central nervous system through the blood-brain barrier in animals.
  • Uses A selective A2A adenosine receptor agonist in myocardial imaging
  • Uses Regadenoson is a selective and potent A2A adenosine receptor agonist (1). The adenosine A2A receptor is a G-protein-coupled receptor and a key therapeutic target for oncologic, inflammatory, Parkinson''s and cardiovascular diseases (2). In rodent studies, it has been shown that co-administration of Regadenoson with Temozolomide (T017775) can increase Temozolomide concentration in the brain (3).
  • Definition ChEBI: Regadenoson is a purine nucleoside.
  • Synthesis The synthesis of regadenoson has been reported in several papers and patents and a scalable procedure is detailed in the scheme. The synthesis was initiated with the reaction of 2- chloroadenosine hemihydrate (94) and hydrazine monohydrate at 40-50 ??C to provide 95 in 81% yield with 99.3% purity. Hydrazine 95 was condensed with ethyl-2-formyl-3- oxopropionate (96) under refluxing IPA to furnish the pyrazole 97 in 77% yield which was collected by filtration and used in next step without further purification. Pyrazole 97 was then reacted with methyl amine at room temperature to provide regadenoson (XV). Although the yield was not reported, the product was collected by simple filtration.

    Synthesis_313348-27-5

  • in vitro regadenoson was selective for the a2a adenosine receptor versus the a1, a2b, and a3 receptors in binding and functional studies. regadenoson was also found to be a full and potent agonist to cause coronary vasodilation, a response that has a very large a2a receptor reserve [1].
  • in vivo in a study of 10 conscious dogs, authors compared intravenously injected regadenoson to that of adenosine. regadenoson caused a dose-dependent increase of coronary blood flow (cbf), whereas adenosine was less potent but produced equivalent hyperemia. thus, authors concluded that regadenoson is a potent coronary vasodilator with a short duration of action, minimal and transient systemic hemodynamic effects, and ease of administration [1].
  • References [1] cerqueira md. the future of pharmacologic stress: selective a2a adenosine receptor agonists. am j cardiol. 2004 jul 22;94(2a):33d-40d; discussion 40d-42d.
REGADENOSON Preparation Products And Raw materials
Raw materials
Preparation Products
REGADENOSON Suppliers
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REGADENOSON Spectrum
313348-27-5, REGADENOSONRelated Search:
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  • C15H18N8O5
  • 71871
  • 1976/3/9
  • 瑞加德松,10 MM DMSO 溶液
  • CVT-3146|||瑞加德松|||LEXISCAN
  • 瑞加德松(ADENOSINE RECEPTOR激动剂)
  • 瑞加浴生
  • XN-API-12112
  • 雷加诺森
  • 瑞加德松一水化合物
  • 瑞加诺生
  • 瑞加德松REGADENOSON
  • A2A腺苷受体激动剂(REGADENOSON)
  • 瑞加德松杂质
  • 瑞加德松原料药
  • 1-(6-氨基-9-((2R,3R,4S,5R)-3,4-二羟基-5-(羟甲基)四氢呋喃-2-基)-9H-嘌呤-2-基)-N-甲基-1H-吡唑-4-甲酰胺
  • 雷加德诺森
  • 瑞加德松
  • 瑞加德松一水合物
  • 类伽腺苷
  • 313348-27-5
  • Regadenoson, 10 mM in DMSO
  • CVT-3146|||Lexiscan
  • 2-[4-[(4-methylamino)carbonyl]-1H-pyrazol-1-yl]-Adenosine
  • Regadenoson monohydrate
  • 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-N-methyl-1H-pyrazole-4-carboxamide
  • Regadenoson Monohydrate (CVT-3146)
  • Regadenoson Impurity 18
  • Regadenoson Impurity 16
  • Regadenoson Impurity
  • LEXISCAN; CVT-3146;
  • CS-1874
  • Adenosine,2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]-
  • 2-[4-(N-Methylcarbamoyl)-1H-pyrazol-4-yl)adenosine
  • 6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside monohydrate
  • 1-(6-Amino-9-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-N-methyl-1H-pyrazole-4-carboxamide monohydrate
  • 6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside
  • 2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]-adenosine

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