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Eletriptan
Systematic (IUPAC) name
(R)-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole
Identifiers
CAS number 143322-58-1
ATC code N02CC06
PubChem 77993
DrugBank APRD00945
ChemSpider 70379
Chemical data
Formula C22H26N2O2S 
Mol. mass 382.52
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 50%
Metabolism CYP3A4
Half life 4 hours
Therapeutic considerations
Pregnancy cat.  ?
Legal status Prescription (Rx)
Routes oral
 Yes check.svgY(what is this?)  (verify)

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.

Contents

Approval and availability

Eletriptan was approved by the U.S. Food and Drug Administration (FDA) on December 26, 2002 for the acute treatment of migraine with or without aura in adults.[1] 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.

Eletriptan is covered by U.S. Patent no. 5545644[2][1] and U.S. Patent no. 6110940;[3][1] the FDA lists the patents as scheduled for expiration on December 26, 2016 and August 29, 2017, respectively.[1]

Mechanism of action

Treatment with Eletriptan is believed to reduce swelling of the blood vessels surrounding the brain. This swelling is associated with the head pain of a migraine attack. Eletriptan 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 Eletriptan.

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

Eletriptan binds with high affinity to the 5-HT[1B, 1D, 1F] receptors.

It has a modest affinity to the 5-HT[1A, 1E, 2B, 7] receptors.

And little to no affinity at the 5-HT[2A, 2C, 3, 4, 5A, 6] 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.

Additional Chemical Names

  • Merck Index: 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole
  • 5-[2-(benzenesulfonyl)ethyl]-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole
  • (R)-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

References

  1. ^ a b c d FDA AccessData entry for Eletriptan Hydrobromide, accessed March 10, 2010
  2. ^ U.S. Patent no. 5545644, John E. Macor & Martin J. Wythes, Indole Derivatives, August 13, 1996
  3. ^ U.S. Patent no. 6110940, Valerie Denise Harding, et al., Salts of an anti-migraine indole derivative, August 29, 2000

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