Eletriptan hydrobromide

Chemical Properties

Eletriptan hydrobromide is Tan Solid

Originator

Relpax,Pfizer

Uses

Relpax is a second generation triptan drug used in the treatment of migraine headaches.

Uses

antibiotic

Uses

Eletriptan hydrobromide is a second generation triptan drug used in the treatment of migraine headaches.

Definition

ChEBI: Eletriptan hydrobromide is a hydrobromide. It has a role as a serotonergic agonist, a vasoconstrictor agent and a non-steroidal anti-inflammatory drug. It contains an eletriptan(1+).

Manufacturing Process

A mixture of the appropriate phenyl vinyl sulfone, tri-o-tolylphosphine, palladium (II) acetate, triethlamine and (R)-5-bromo-3-(Nmethylpyrrolidinylmethyl)-1H-indole in anhydrous acetonitrle was heated at reflux under nitrogen. The resultant reaction mixture was evaporated under reduced pressure, and the residue was column chromatographed using silica gel and elution with methylene chloride/absolute ethanol/ammonia to afford the (R )-5-trans-(2-phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)- 1H-indole.
A solution of (R)-5-trans-(2-phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2- ylmethyl)-1H-indole and 10% Pd/C in ethanolic hydrogen chloride (prepared from absolute ethanol and acetyl chloride and N,N-dimethylformamide was shaken under a hydrogen atmosphere at room temperature). The resultant reaction mixture was filtered through diatomaceous earth (Celite trademark), washed with absolute ethanol, and the combined filtrates were evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was separated, washed with water, brine, dried(Na2SO4), and evaporated under reduced pressure to afford a oil product. Column chromatography of this product using silica gel and elution with methylene chloride/absolute ethanol/ammonia afforded the appropriate (R)-5- (2-phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole.
The salt eletriptan hydrobromide may be produced by reaction of the (R)-5- (2-phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole with hydrobromic acid.

brand name

Relpax (Pfizer).

Therapeutic Function

Serotonin agonist

Biological Activity

Orally active, selective 5-HT 1B/1D receptor agonist. Produces a dose-dependent reduction in carotid artery blood flow in vivo . Displays antimigraine activity.

storage

room temperature (desiccate)