8111. Ranolazine

Nomenclature

CAS number: 95635-55-5
N-(2,6-Dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamide; (±)-4-[2-hydroxy-3-(o-methoxyphenoxy)propyl]-1-piperazineaceto-2′,6′-xylidide; (±)-1-[3-(2-methoxyphenoxy)-2-hydroxypropyl]-4-[N-(2,6-dimethylphenyl)carbamoylmethyl]piperazine; Ranexa (CV Therapeutics).
C24H33N3O4; mol wt 427.54.
C 67.42%, H 7.78%, N 9.83%, O 14.97%.

Description and references

Anti-ischemic agent which modulates myocardial metabolism. Prepn: A. F. Kluge et al., EP 126449; eidem, US 4567264 (1984, 1986 both to Syntex). HPLC resolution of enantiomers: E. Delée et al., Chromatographia 24, 357 (1987). Clinical trial in angina: B. R. Chaitman et al., J. Am. Coll. Cardiol. 43, 1375 (2004). Review of pharmacology and clinical development: J. G. McCormack et al., Gen. Pharmacol. 30, 639-645 (1998); R. S. Schofield, J. A. Hill, Expert Opin. Invest. Drugs 11, 117-123 (2002).

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 95635-56-6
RS-43285.
C24H33N3O4.2HCl; mol wt 500.46.
C 57.60%, H 7.05%, N 8.40%, O 12.79%, Cl 14.17%.

Properties

White crystalline powder from methanol/ether, mp 164-166°. Readily sol in water.

Therapeutic Category

Antianginal.

Keywords

Antianginal