Eletriptan

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Column 1
Relpax, others
UK-116044; UK116044
Monograph
a603029
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}
US DailyMed: Eletriptan
AU: B1
By mouth
Serotonin 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptor agonist; Triptan; Antimigraine agent
N02CC06 (WHO)
AU: S3 (Pharmacist only) & S4
CA: ℞-only
UK: POM (Prescription only)
US: ℞-only
In general: ℞ (Prescription only)
50%
Mainly CYP3A4
4 hours
IUPAC name
3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole
143322-58-1 YHBr: 177834-92-3 Y
77993HBr: 656631
40
DB00216 YHBr: DBSALT000884 Y
70379 YHBr: 570985 Y
22QOO9B8KIHBr: M41W832TA3 Y
D07887 YHBr: D01973 Y
CHEBI:50922 YHBr: CHEBI:61176 Y
ChEMBL1510 YHBr: ChEMBL1201003 Y
DTXSID9046861
100.167.337
C22H26N2O2S
382.52 g·mol−1
Interactive image
SMILES
CN1CCC[C@@H]1Cc3c[nH]c4ccc(CCS(=O)(=O)c2ccccc2)cc34
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,5-6,11-13,15H2,1H3/t19-/m1/s1 YKey:PWVXXGRKLHYWKM-LJQANCHMSA-N Y
.mw-parser-output .nobold{font-weight:normal}  (verify)

Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication 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.

Eletriptan is a therapeutic alternative on the World Health Organization's List of Essential Medicines.

Eletriptan was approved by the United States Food and Drug Administration (FDA) in December 2002, for the acute treatment of migraine with or without aura in adults. It is available only by prescription in the United States, Canada, and Australia. 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 contraindicated in patients with various diseases of the heart and circulatory system, such as angina pectoris, severe hypertension, and heart failure, as well as in patients that have had a stroke or heart attack. This is due to the unusual side effect of coronary vasoconstriction due to serotonin 5-HT1B receptor agonism, which can precipitate a heart attack in those already at risk. It is also contraindicated in severe kidney (renal) or liver (hepatic) impairment due to its extensive liver metabolism through CYP3A4.

Common side effects include hypertension, tachycardia, headache, dizziness, drowsiness, and symptoms similar to angina pectoris. Severe allergic reactions have been seen rarely.

Strong inhibitors of the liver enzyme CYP3A4, such as erythromycin and ketoconazole, significantly increase blood plasma concentration of eletriptan and should be separated by at least 72 hours. Ergot alkaloids, such as dihydroergotamine, add to the drug's hypertensive effect and should be separated by at least 24 hours.

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Target	Affinity (Ki, nM)
5-HT1A	1.9–45 (Ki)417–1,820 (EC50Tooltip half-maximal effective concentration)
5-HT1B	0.52–15.1 (Ki)8.1–60 (EC50)83% (EmaxTooltip maximal efficacy)
5-HT1D	0.10–1.5 (Ki)0.63–0.91 (EC50)
5-HT1E	40–62 (Ki)30–126 (EC50)
5-HT1F	5–20 (Ki)7.4–132 (EC50)
5-HT2A	1,150–>3,160 (Ki)851 (EC50)
5-HT2B	447 (Ki)155 (EC50)
5-HT2C	>3,160 (Ki)ND (EC50)
5-HT3	>3,160 (mouse)
5-HT4	>3,160 (guinea pig)
5-HT5A	977–1,584 (rat)
5-HT6	525
5-HT7	200 (Ki)355 (EC50)
α1A–α1D	ND
α2A–α2C	ND
β1–β3	ND
D1–D5	ND
H1–H4	ND
M1–M5	ND
I1, I2	ND
σ1, σ2	ND
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	ND
NETTooltip Norepinephrine transporter	ND
DATTooltip Dopamine transporter	ND
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

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-HT1B, 1D, [1F]](https://en.wikipedia.org/wiki/5-HT1F) receptors. It has a modest affinity to the [5-HT1A, 1E, 2B, [7]](https://en.wikipedia.org/wiki/5-HT7) receptors, and little to no affinity at the [5-HT2A, 2C, 3, 4, 5A, [6]](https://en.wikipedia.org/wiki/5-HT6) receptors.

Eletriptan has no significant affinity or pharmacological activity at adrenergic α1, α2, or β; dopaminergic D1 or D2; muscarinic; or opioid receptors. Eletriptan could be efficiently co-administered 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-HT1 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.

The drug is also notable in being a weak serotonin 5-HT2A receptor agonist (EC50Tooltip half-maximal effective concentration = 851 nM), albeit with about two to three orders of magnitude lower activational potency than at the serotonin 5-HT1B and 5-HT1D receptors.

Eletriptan is a tryptamine and pyrrolidinylmethylindole derivative and is a 5-substituted and cyclized tryptamine derivative of the psychedelic drug dimethyltryptamine (DMT).

The experimental log P is 3.9 and its predicted log P is 1.78 to 4.1.

• 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

Eletriptan was approved for medical use in the United States in 2002. It was covered by U.S. Patent no. 5545644 and U.S. Patent no. 6110940; both now expired.

Eletriptan is sold in the United States, Canada, Australia, and the United Kingdom under the brand name Relpax, and in several other countries under the brand name Relert.

In the United States, Relpax is marketed by Viatris after Upjohn was spun off from Pfizer.

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• Eletriptan - Isomer Design

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