Ondansetron
Title: Ondansetron
CAS Registry Number: 99614-02-5
CAS Name: 1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one
Molecular Formula: C18H19N3O
Molecular Weight: 293.36
Percent Composition: C 73.70%, H 6.53%, N 14.32%, O 5.45%
Literature 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). 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). 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).
Properties: Crystals from methanol, mp 231-232°.
Melting point: mp 231-232°
 
Derivative Type: Hydrochloride dihydrate
CAS Registry Number: 99614-01-4
Manufacturers' Codes: GR-38032F; GR-C507/75; SN-307
Trademarks: Zofran (GSK); Zophren (GSK)
Molecular Formula: C18H19N3O.HCl.2H2O
Molecular Weight: 365.85
Percent Composition: 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.
Melting point: mp 178.5-179.5°
pKa: pKa 7.4
 
Derivative Type: 3S-Form
Properties: [a]D25 -14° (c = 0.19 in methanol).
Optical Rotation: [a]D25 -14° (c = 0.19 in methanol)
 
Derivative Type: 3R-Form
Properties: [a]D24 +16° (c = 0.34 in methanol).
Optical Rotation: [a]D24 +16° (c = 0.34 in methanol)
 
Therap-Cat: Antiemetic.
Keywords: Antiemetic; Serotonin Receptor Antagonist.

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