8241. Rizatriptan

Nomenclature

CAS number: 144034-80-0
N,N-Dimethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indole-3-ethanamine; 3-[2-(dimethylamino)ethyl]-5-(1H-1,2,4-triazol-1-ylmethyl)indole; N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3yl]ethylamine.
C15H19N5; mol wt 269.34.
C 66.89%, H 7.11%, N 26.00%.

Description and references

Selective serotonin 5-HT1B/1D receptor agonist; structurally derived from tryptamine. Prepn: R. Baker et al., EP 497512; eidem, US 5298520 (1992, 1994 both to Merck Sharp & Dohme); and binding characteristics: L. J. Street et al., J. Med. Chem. 38, 1799 (1995). Synthesis: C. Chen et al., Tetrahedron Lett. 35, 6981 (1994). Clinical pharmacokinetics: H. Cheng et al., Biopharm. Drug Dispos. 17, 17 (1996). LC-MS determn in plasma: D. A. McLoughlin et al., J. Chromatogr. A 726, 115 (1996). Comparative clinical trial in treatment of migraine: J. U. Adelman et al., Neurology 57, 1377 (2001). Review of pharmacology and therapeutic efficacy: K. Wellington, G. L. Plosker, Drugs 62, 1539-1574 (2002); of development and clinical experience: A. V. Krymchantowski, M. E. Bigal, Expert Rev. Neurother. 5, 597-603 (2005).

Chemical structure

Properties

mp 120-121°.

Derivative

Benzoate.

Nomenclature

CAS number: 145202-66-0
MK-0462; MK-462; Maxalt (Merck & Co.).
C15H19N5.C7H6O2; mol wt 391.47.
C 67.50%, H 6.44%, N 17.89%, O 8.17%.

Description and references

Crystal structure: K. Ravikumar et al., Acta Crystallogr. E63, 1958 (2007).

Properties

White to off-white, crystalline solid, mp 178-180°. Sol in methanol. Soly in water (25°C): ≈42 mg/ml (expressed as free base).

Therapeutic Category

Antimigraine.

Keywords

Antimigraine; Serotonin Receptor Agonist