10292. Regadenoson

Nomenclature

CAS number: 313348-27-5
2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine; 1-(6-amino-9-β-d-ribofuranosyl-9H-purin-2-yl)-N-methyl-1H-pyrazole-4-carboxamide; 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-y1}pyrazol-4N-methylcarboxamide ; CVT-3146.
C15H18N8O5; mol wt 390.35.
C 46.15%, H 4.65%, N 28.71%, O 20.49%.

Description and references

A2A-Adenosine receptor agonist; pharmacologic stress agent for use in cardiac imaging by producing coronary vasodilation. Prepn: J. A. Zablocki et al., WO 0078779; eidem, US 6403567 (2000, 2002 both to CV Therapeutics). Receptor binding study and coronary vasodilatory effects: Z. Gao et al., J. Pharmacol. Exp. Ther. 298, 209 (2001) PubMed. Structure-affinity relationship: V. P. Palle et al., Bioorg. Med. Chem. Lett. 12, 2935 (2002) DOI PubMed. Clinical pharmacokinetics in patients with impaired renal function: T. Gordi et al., J. Clin. Pharmacol. 47, 825 (2007) DOI PubMed. Clinical effect on coronary blood flow: H. D. Lieu et al., J. Nucl. Cardiol. 14, 514 (2007) DOI PubMed. Clinical comparison with adenosine in myocardial perfusion imaging: A. E. Iskandrian et al., ibid. 645 DOI PubMed. Review of development and clinical experience: H. Eggebrecht, M. Gssl, Curr. Opin. Investig. Drugs 7, 264-271 (2006) PubMed.

Chemical structure

Properties

Sol in methanol, phosphate-buffered saline.

Derivative

Monohydrate.

Nomenclature

CAS number: 875148-45-1
Lexiscan (Astellas).
C15H18N8O5.H2O; mol wt 408.37.
C 44.12%, H 4.94%, N 27.44%, O 23.51%.

Therapeutic Category

Diagnostic aid (cardiac stress testing).

Keywords

Vasodilator (Coronary); Adenosine Receptor Agonist; Diagnostic Aid