Eletriptan

Eletriptan
Clinical data

Trade names	Relpax
AHFS/Drugs.com	Monograph
MedlinePlus	a603029
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	oral
ATC code	N02CC06 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	50%
Metabolism	CYP3A4
Biological half-life	4 hours
Identifiers
IUPAC name (R)-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole
CAS Number	143322-58-1^Y
PubChem (CID)	77993
IUPHAR/BPS	40
DrugBank	DB00216^Y
ChemSpider	70379^Y
UNII	22QOO9B8KI^Y
KEGG	D01973^N
ChEBI	CHEBI:50922^Y
ChEMBL	CHEMBL1510^Y
ECHA InfoCard	100.167.337
Chemical and physical data
Formula	C₂₂H₂₆N₂O₂S
Molar mass	382.52 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(c1ccccc1)CCc4ccc2c(c(cn2)C[C@@H]3N(C)CCC3)c4
InChI InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-137T56T^N Key:PWVXXGRKLHYWKM-LJQANCHMSA-N^Y
^NY (what is this?)

Eletriptan (trade name Relpax, used in the form of eletriptan hydrobromide) is a second generation triptan drug intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc. It is sold in the US and Canada under the brand name Relpax, and in several other countries under the brand name Relert.

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. 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, 40 mg and 80 mg strengths.

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

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 receptor agonist, specifically an agonist of certain 5-HT₁ family receptors. 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.

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Wikipedia