My watch list
my.bionity.com  
Login  

Eletriptan



Eletriptan
Systematic (IUPAC) name
3-[((2R)-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole
Identifiers
CAS number 143322-58-1
ATC code N02CC06
PubChem 77993
DrugBank APRD00945
Chemical data
Formula C22H26N2O2S 
Mol. mass 382.52 g/mol
Pharmacokinetic data
Bioavailability 50%
Metabolism CYP3A4
Half life 4 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status

prescription

Routes oral

Eletriptan Hydrobromide is the active metabolite of Relpax, the only FDA-approved eletriptan product currently on the market in the U.S. Eletriptan is a second generation triptan drug developed by Pfizer Inc for the treatment of migraine headaches.

Additional recommended knowledge

Approval and availability

Relpax was approved by the U.S. FDA on December 26, 2002 for the acute treatment of migraine with or without aura in adults. It is available only by prescription in the United States and Canada. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 20 mg and 40 mg strengths.

Relpax tablets for oral administration contain 24.2 mg or 48.5 mg of eletriptan hydrobromide equivalent to 20 mg or 40 mg of eletriptan, respectively. Each tablet also contains the inactive ingredients microcrystalline cellulose NF, lactose NF, croscarmellose sodium NF, magnesium stearate NF, titanium dioxide USP, hydroxypropyl methylcellulose NF, triacetin USP and FD&C Yellow No. 6 aluminum lake.

Mode of action

Treatment with Relpax reduces swelling of blood vessels surrounding the brain. This swelling is associated with the headache pain of a migraine attack. Relpax blocks the release of substances from nerve endings that cause more pain and other symptoms like nausea, and sensitivity to light and sound. It is thought that these actions contribute to relief of symptoms by Relpax.

Eletriptan is a serotonin agonist. Specifically, it is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist.

Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors, and little or no affinity for 5-HT2A, 5-HT2C, 5-HT3, 5-HT4, 5-HT5A and 5-HT6 receptors. Eletriptan has no significant affinity or pharmacological activity at adrenergic alpha1, alpha2, or beta; dopaminergic D1 or D2; muscarinic; or opioid receptors. Eletriptan could be efficiently co-administrated with nitric oxide synthase (NOS's) inhibitors for the treatment of NOS-dependent diseases (US patent US 2007/0254940)

Two theories have been proposed to explain the efficacy of 5-HT receptor agonists in migraine. One theory suggests that activation of 5-HT1 receptors located on intracranial blood vessels, including those on the arteriovenous anastomoses, leads to vasoconstriction, which is correlated with the relief of migraine headache. The other hypothesis suggests that activation of 5-HT1 receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

Chemical name: (R)-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Eletriptan". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE