8997. Sumatriptan

Nomenclature

CAS number: 103628-46-2
3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide; GR-43175.
C14H21N3O2S; mol wt 295.40.
C 56.92%, H 7.17%, N 14.22%, O 10.83%, S 10.85%.

Description and references

Serotonin 5HT1-receptor agonist. Prepn: M. D. Dowle, I. H. Coates, DE 3320521; eidem, US 4816470; A. W. Oxford, GB 2162522 (1983, 1989, 1986 all to Glaxo). Receptor binding studies: P. P. A. Humphrey et al., Br. J. Pharmacol. 94, 1123 (1988); P. Schoeffter, D. Hoyer, Arch. Pharmacol. 340, 135 (1989). LC-MS determn in plasma: J. Oxford, M. S. Lant, J. Chromatogr. 496, 137 (1989). Clinical evaluations in migraine: A. Doenicke et al., Lancet 1, 1309 (1988); Subcutaneous Sumatriptan International Study Group, N. Engl. J. Med. 325, 316 (1991); in acute cluster headache: Sumatriptan Cluster Headache Study Group, ibid. 322. Review of pharmacology and clinical experience: S. J. Peroutka, Headache 30 (Suppl. 2), 554-560 (1990).

Chemical structure

Properties

mp 169-171°.

Derivative

Succinate.

Nomenclature

CAS number: 103628-48-4
GR-43175C; Imigran (GSK); Imitrex (GSK); Imiject (GSK).
C14H21N3O2S.C4H6O4; mol wt 413.49.
C 52.28%, H 6.58%, N 10.16%, O 23.22%, S 7.75%.

Properties

mp 165-166°.

Therapeutic Category

Antimigraine.

Keywords

Antimigraine; Serotonin Receptor Agonist