Eletriptan

drugbox
IUPAC_name = 3- [((2R)-1-methylpyrrolidin-2-yl)methyl] -5-(2-phenylsulfonylethyl)- 1H-indole

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CAS_number = 143322-58-1
ATC_prefix = N02
ATC_suffix = CC06
ATC_supplemental =
PubChem = 77993
DrugBank = APRD00945
C=22 | H=26 | N=2 | O=2 | S=1
molecular_weight = 382.52 g/mol
bioavailability = 50%
protein_bound =
metabolism = CYP3A4
elimination_half-life = 4 hours
pregnancy_category =
legal_status = prescription
routes_of_administration = oral

Eletriptan (also known as eletriptan hydrobromide) is a second generation triptan drug marketed and manufactured by Pfizer Inc for the treatment of migraine headaches. It is sold in the US under the brand name Relpax.

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.

Mechanism 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

External links

* [http://www.relpax.com Relpax] Official homepage by Pfizer
* [http://www.duchs.com/information/Relpax Relpax Information] Fact Sheet
* [http://www.fda.gov/cder/foi/label/2002/21016_relpax_lbl.pdf] FDA Approved Label (Full Prescribing Information)