Wednesday, March 11, 2015


Common name: Frovatriptan; SB-209509; VML-251; Frovatriptan Succinate
Trademarks: Frova
Molecular Formula: C14H17N3O
CAS Registry Number: 158747-02-5; 158930-18-8 ((S)-isomer), 158747-09-2 (racemate), 158930-17-7 (succinate)
CAS Name: (3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide
Molecular Weight: 243.304
SMILES: CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O
InChI: InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1
Activity: Treatment of  Migraines; Serotonin Antagonists; Serotonin Receptor Agonists; Anti-migraine Agents; Affinity for 5-HT1B/1D Receptors; Treatment of Menstrual Migraine
Status: Launched 2001
Originator: SmithKline;Vernalis/Elan

It appears SKB has filed many patents for this compound with same procedure repeated in them. The difference is few patents have other derivatives, and/or different racemic resolution schemes.

Frovatriptan synthesis: WO1993000086A1

Frovatriptan synthesis: US5616603A

Frovatriptan synthesis: US5618948A

1. Gaster, L. M.; et. al. Use of tetrahydrocarbazone derivatives as 5ht1 receptor agonists. WO1993000086A1
2. Borrett, G. T.; et. al. Treating migraines. US5616603A
3. Borrett, G. T.; et. al. Treatment of 6-carboxamido-3-methylamino-1,2,3,4-tetrahydrocarbazole with 2-pyrrolidone-5-carboxylic acid, crystallization. US5618948A
4. Markus, F.; et. al. Frovatriptan review. Expert Opin Pharmacother 2007, 8(17), 3029-3033. (activity)
5. Kelman, L. Review of frovatriptan in the treatment of migraine. Neuropsychiatr Dis Treat 2008, 4(1), 49-54. (activity)

For more drugs and their synthesis: Synayurajan database