3411. Dolasetron

Nomenclature

CAS number: 115956-12-2
1H-Indole-3-carboxylic acid (2α,6α,8α,9aβ)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester; endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one; MDL-73147.
C19H20N2O3; mol wt 324.37.
C 70.35%, H 6.21%, N 8.64%, O 14.80%.

Description and references

Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Prepn: M. W. Gittos, EP 266730; idem et al., US 4906755 (1988, 1990 both to Merrell Dow). Binding study: P. H. Boeijinga et al., Eur. J. Pharmacol. 219, 9 (1992). Pharmacology: R. C. Miller et al., Drug Dev. Res. 28, 87 (1993). Clinical pharmacokinetics: H. Boxenbaum et al., Biopharm. Drug Dispos. 13, 693 (1992); eidem, ibid. 14, 131 (1993). GC-MS and LC determn in plasma: T. A. Gillespie et al., J. Pharm. Biomed. Anal. 11, 955 (1993). Clinical trial in emetogenic chemotherapy: A. A. Fauser et al., Eur. J. Cancer 32A, 1523 (1996); for prevention of postoperative nausea: S. G. Graczyk et al., Anesth. Analg. 84, 325 (1997); B. K. Philip et al., J. Clin. Anesth. 12, 1 (2000). Review of veterinary use: G. K. Ogilvie, J. Am. Anim. Hosp. Assoc. 36, 481-483 (2000).

Chemical structure

Derivative

Methanesulfonate.

Nomenclature

CAS number: 115956-13-3
Dolasetron mesylate; MDL-73147EF; Anzemet (Sanofi-Aventis).
C19H20N2O3.CH3SO3H; mol wt 420.48.
C 57.13%, H 5.75%, N 6.66%, O 22.83%, S 7.63%.

Properties

Crystalline solid, mp 278°. Freely sol in water, propylene glycol; slightly sol in alcohol.

Therapeutic Category

Antiemetic.

Therapeutic Category (Veterinary)

Antiemetic.

Keywords

Antiemetic; Serotonin Receptor Antagonist