6848. Ondansetron

Nomenclature

CAS number: 99614-02-5
1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one.
C18H19N3O; mol wt 293.36.
C 73.70%, H 6.53%, N 14.32%, O 5.45%.

Description and references

Specific serotonin (5HT3) receptor antagonist. Prepn: I. H. Coates et al., EP 191562; eidem, US 4695578 (1986, 1987 both to Glaxo). Pharmacology: A. Butler et al., Br. J. Pharmacol. 94, 397 (1988). LC-MS/MS determn in plasma: Y. Dotsikas et al., J. Chromatogr. B 836, 79 (2006). Clinical trials in cancer chemotherapy-induced nausea and vomiting: M. G. Kris et al., J. Clin. Oncol. 6, 659 (1988); L. Cubeddu et al., N. Engl. J. Med. 322, 810 (1990); M. Marty et al., ibid. 816. Clinical evaluation in treatment of bulimia: P. L. Faris et al., Lancet 355, 792 (2000); in early onset alcoholism: B. A. Johnson et al., J. Am. Med. Assoc. 284, 963 (2000); in radiotherapy-induced nausea and emesis: J. P. LeBourgeois et al., Clin. Oncol. 11, 340 (1999). Review of pharmacology and therapeutic use: A. Markham, E. M. Sorkin, Drugs 45, 931-952 (1993); of clinical pharmacokinetics: K. H. Simpson, F. M. Hicks, J. Pharm. Pharmacol. 48, 774-781 (1996).

Chemical structure

Properties

Crystals from methanol, mp 231-232°.

Derivative

Hydrochloride dihydrate.

Nomenclature

CAS number: 99614-01-4
GR-38032F; GR-C507/75; SN-307; Zofran (GSK); Zophren (GSK).
C18H19N3O.HCl.2H2O; mol wt 365.85.
C 59.09%, H 6.61%, N 11.49%, O 13.12%, Cl 9.69%.

Properties

White crystalline solid from water/isopropanol, mp 178.5-179.5°. pKa 7.4.

Derivative

3S-Form.

Nomenclature

CAS number: 99614-58-1

Properties

[α]D25 -14° (c = 0.19 in methanol).

Derivative

3R-Form.

Nomenclature

CAS number: 99614-60-5

Properties

[α]D24 +16° (c = 0.34 in methanol).

Therapeutic Category

Antiemetic.

Therapeutic Category (Veterinary)

Antiemetic.

Keywords

Antiemetic; Serotonin Receptor Antagonist