| Identification | Back Directory | [Name]
REGADENOSON | [CAS]
313348-27-5 | [Synonyms]
REGADENOSON
Regadenoson(CVT-3146)
Regadenoson monohydrate
2-[4-(N-Methylcarbamoyl)-1H-pyrazol-4-yl)adenosine
2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]-adenosin
2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]-adenosine
Adenosine,2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]-
6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside
6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside monohydrate
Regadenoson
6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside
6-Amino-2-[4-(methylcarbamoyl)-1H-pyrazol-1-yl]purine-9-yl-beta-D-ribofuranoside Regadenoson
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 | [Molecular Formula]
C15H18N8O5 | [MDL Number]
MFCD09832544 | [MOL File]
313348-27-5.mol | [Molecular Weight]
390.35 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
158-160°C | [density ]
1.98±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
13.07±0.70(Predicted) | [color ]
Off-White to Pale Brown | [InChIKey]
LZPZPHGJDAGEJZ-AKAIJSEGSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=C(N4C=C(C(NC)=O)C=N4)N=3)N)N=C2)[C@H](O)[C@@H]1O | [CAS DataBase Reference]
313348-27-5 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
A selective A2A adenosine receptor agonist in myocardial imaging | [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. | [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. | [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.
| [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]. | [storage]
Store at -20°C | [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. |
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