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Eletriptan

Eletriptan is a selective serotonin (5-HT1B/1D) receptor medication approved for the acute treatment of headaches with or without aura in adults. Marketed under the brand name Relpax by and as eletriptan tablets, it is available as oral tablets in 20 mg and 40 mg strengths and does not prevent future migraines or reduce their frequency. Chemically known as 5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole with the molecular formula C22H26N2O2S, eletriptan has a of approximately 50% and a of about 4 hours. Eletriptan exerts its therapeutic effects by activating 5-HT1B receptors on cerebral blood vessels to induce vasoconstriction and by stimulating 5-HT1D receptors on sensory nerves to inhibit neurogenic inflammation and the release of pro-inflammatory neuropeptides. It is primarily metabolized in the liver via the cytochrome P450 3A4 (CYP3A4) enzyme, producing an active N-demethylated metabolite with similar but less potent serotonin agonist activity. The drug reaches peak plasma concentrations 1.5 to 2 hours after oral administration and is primarily eliminated in the feces and urine, with about 90% via non-renal routes. For administration, eletriptan is typically taken as a single 20 mg or 40 mg dose at the onset of a attack, with a possible second dose after at least 2 hours if needed, but not exceeding 80 mg in 24 hours. The safety of treating more than 3 headaches in any 30-day period has not been established. It should not be used prophylactically or during the phase alone. Common adverse effects include , , , flushing, and sensations of chest tightness or pressure, while serious risks involve , myocardial ischemia, or , particularly in patients with cardiovascular risk factors. Contraindications include , uncontrolled , to the drug, and concurrent use with potent inhibitors (e.g., ) within 72 hours; use with other agents is cautioned due to risk of . Monitoring for cardiovascular effects and response is recommended in at-risk individuals.

Medical Uses

Indications

Eletriptan is approved for the acute treatment of headaches with or without in adults. It is not indicated for prophylactic therapy, the treatment of , or basilar-type . Eletriptan is included on the World Health Organization's Model List of (24th list, 2025) as an effective and safe abortive agent for acute attacks in adults. A 2024 network of licensed oral drugs for acute management demonstrated eletriptan's superior efficacy over newer agents such as and , with odds ratios for pain freedom at 2 hours ranging from 1.46 to 3.01 compared to other interventions. In pivotal clinical trials, the 40 mg dose of eletriptan achieved response rates of 55-77% at 2 hours post-dose, significantly outperforming .

Dosage and Administration

Eletriptan is available as oral tablets in 20 mg and 40 mg strengths, formulated as orange, round, convex, film-coated tablets for immediate release. The recommended initial dose for the acute treatment of in adults is 20 mg or 40 mg taken orally as soon as symptoms appear, with a maximum single dose of 40 mg. If the persists or recurs, a second dose of 20 mg or 40 mg may be taken at least 2 hours after the initial dose, but the total dose should not exceed 80 mg in any 24-hour period. The safety of treating more than three attacks in any 30-day period has not been established. Tablets should be swallowed whole with and may be taken with or without , as does not significantly affect absorption. No specific administration instructions beyond these are required for standard use. Dose adjustments are not necessary for patients with mild to moderate renal or hepatic , nor for differences in age, gender, or race. However, no dose adjustment is needed even in severe renal , while eletriptan is not recommended for use in severe hepatic due to increased . Caution is advised in elderly patients, as they may experience greater increases in . Recent research has explored alternative formulations to potentially accelerate ; a 2023 study developed and evaluated statistically optimized polymeric buccal films of eletriptan , demonstrating promising for faster transmucosal delivery, though this formulation is not yet approved for clinical use.

Safety and Tolerability

Contraindications

Eletriptan is contraindicated in patients with ischemic or vasospastic , including those with a history of , Prinzmetal's , or other forms of , due to the risk of serious cardiovascular events from its vasoconstrictive effects. It is also prohibited in individuals with Wolff-Parkinson-White syndrome or other cardiac accessory conduction pathway disorders, as these conditions increase the potential for arrhythmias. The drug must not be used in patients with a history of cerebrovascular events, such as or , or in those with hemiplegic or basilar , owing to the heightened risk of cerebral and ischemia. Similarly, eletriptan is contraindicated in the presence of or ischemic bowel disease, where vascular compromise could be exacerbated. Uncontrolled represents another absolute , as the medication may further elevate . Eletriptan should not be administered within 24 hours of treatment with another 5-HT1B/1D (triptan) or an ergotamine-containing or ergot-type medication, to avoid additive effects on the and vascular systems. Concurrent or recent use (within 72 hours) of potent inhibitors, such as , , , troleandomycin, , , or nelfinavir, is also contraindicated due to significantly increased exposure to eletriptan, potentially leading to excessive . Hypersensitivity to eletriptan hydrobromide or any component of the formulation is an absolute , with reports of and in such cases.

Use in Specific Populations

Risk Summary: Based on findings from animal studies, eletriptan may cause fetal harm when administered to a pregnant . There are limited data on eletriptan use in pregnant women to inform a drug-associated risk. The background risk of major birth defects and for the indicated is unknown. In the U.S. general population, the estimated background risk of major birth defects and miscarriage in clinically recognized pregnancies is 2% to 4% and 15% to 20%, respectively.

Lactation

Eletriptan is present in human . There are no data on the effects of eletriptan on the breastfed or the effects of the on production. The developmental and health benefits of should be considered along with the mother's clinical need for eletriptan and any potential adverse effects on the breastfed from eletriptan or from the underlying maternal condition. The time to maximum concentration (Tmax) after administration of a 40 dose of eletriptan is 1.5 hours, and the is approximately 4 hours. Infants exposed to eletriptan through are expected to have low levels of exposure, but should be avoided for 24 hours after .

Pediatrics

Safety and effectiveness of eletriptan have not been established in pediatric patients.

Geriatrics

Clinical studies of eletriptan did not include sufficient numbers of subjects aged 65 and over to determine whether they respond differently from younger subjects.

Renal Impairment

No dose adjustment is necessary for patients with mild to moderate renal impairment. Experience with eletriptan in patients with severe renal impairment is limited.

Hepatic Impairment

No dose adjustment is necessary for patients with mild to moderate hepatic impairment. The use of eletriptan in patients with severe hepatic impairment is not recommended due to limited pharmacokinetic data.

Adverse Effects

Eletriptan is generally well-tolerated, with most adverse effects being mild to moderate and transient in nature. Common adverse effects, occurring at incidences of 1% to 10% and greater than , include (weakness or ), (drowsiness), , , (tingling sensations), dry mouth, and sensations of chest tightness, , or pressure. These effects are often dose-related, with higher incidences observed at the 40 mg and 80 mg doses compared to 20 mg; for example, asthenia occurred in 10% of patients receiving 80 mg versus 5% at 40 mg and 4% at 20 mg. Less common effects (1% to 10%) may include flushing or feelings of warmth, as well as initial worsening of in some users. The following table summarizes the incidence of selected adverse reactions from placebo-controlled clinical trials (≥2% and >):
Adverse Reaction (n=988)20 mg (n=431)40 mg (n=1774)80 mg (n=1932)
Asthenia3%4%5%10%
4%3%6%7%
3%3%6%7%
5%4%5%8%
2%3%3%4%
Dry mouth2%2%3%4%
Chest tightness/pain/pressure1%1%2%4%
Management of common effects typically involves symptomatic relief, such as rest for or , and they usually resolve without . Discontinuation due to adverse effects is uncommon, with rates around 8% in long-term studies, and user-reported data from large databases indicate high tolerability, with eletriptan associated with positive outcomes in approximately 78% of cases. Serious adverse effects are rare (<1%) but can be life-threatening, including coronary vasospasm, myocardial infarction, stroke, serotonin syndrome (particularly when combined with serotonergic agents), and anaphylaxis. These events, such as myocardial ischemia or cerebrovascular accidents, have been reported within hours of administration, often in patients with cardiovascular risk factors. Immediate medical attention is required for symptoms like severe chest pain, sudden weakness, confusion, or difficulty breathing, and eletriptan should be discontinued if such reactions occur. Post-marketing surveillance has identified additional rare events, including seizures, vomiting, ischemic colitis, and hypersensitivity reactions such as angioedema. Patients with contraindications, such as uncontrolled hypertension, should avoid use to minimize these risks.

Drug Interactions

Eletriptan undergoes metabolism primarily via the enzyme, leading to significant pharmacokinetic interactions with inhibitors of this pathway. Potent CYP3A4 inhibitors, such as , itraconazole, and ritonavir, can substantially increase eletriptan exposure, with clinical studies showing approximately a 3-fold increase in maximum plasma concentration (Cmax) and up to a 6-fold increase in area under the curve () when co-administered with ketoconazole. Moderate CYP3A4 inhibitors, including erythromycin and verapamil, also elevate exposure, typically resulting in about a 2-fold increase in Cmax and 3- to 4-fold increase in for erythromycin, and similar 2-fold Cmax and 3-fold increases for verapamil. Pharmacodynamic interactions with eletriptan primarily involve additive effects on vascular tone and serotonin systems. Co-administration with ergotamines or other within 24 hours is contraindicated due to the risk of additive , which may lead to serious cardiovascular events. Additionally, concurrent use with selective serotonin reuptake inhibitors (SSRIs) or serotonin-norepinephrine reuptake inhibitors (SNRIs) carries a risk of , characterized by symptoms such as agitation, hallucinations, and autonomic instability; close monitoring is advised, and discontinuation may be necessary if symptoms occur. Eletriptan shows no clinically significant interactions with certain common agents. Oral contraceptives do not alter the frequency or severity of adverse reactions associated with eletriptan. slightly increases eletriptan Cmax by 10% and by 33%, but no dosage adjustment is required. Similarly, has no notable interaction with eletriptan. Clinical recommendations from the FDA prescribing information emphasize caution with inhibitors: avoid eletriptan within 72 hours of potent inhibitors, and for moderate inhibitors, consider monitoring or using the lowest effective dose of eletriptan. Patients should separate eletriptan administration from ergotamines or other by at least 24 hours, and healthcare providers should inform patients of risks when combining with SSRIs or SNRIs.

Pharmacology

Mechanism of Action

Eletriptan acts as a selective primarily at the serotonin 5-HT1B and 5-HT1D receptors, exhibiting high affinity for these subtypes as well as high affinity for the 5-HT1F receptor. This binding profile enables eletriptan to target specific pathways involved in pathophysiology without significant interaction with other serotonin receptor subtypes, such as 5-HT2A or 5-HT2C, which are associated with broader cardiovascular effects. Receptor binding studies have reported values of approximately 3.1 nM at the 5-HT1B receptor and 0.92 nM at the 5-HT1D receptor, underscoring its potent interaction with these targets. The therapeutic effects of eletriptan in relief stem from its activation of 5-HT1B receptors on the cells of intracranial and extracerebral cranial blood vessels, inducing that counteracts the implicated in attacks. This vasoconstrictive action is particularly pronounced in the carotid arterial bed and helps alleviate the throbbing pain characteristic of migraines by reducing neurogenic inflammation around affected vessels. Concurrently, eletriptan's agonism at 5-HT1D receptors, located on sensory nerve endings of the trigeminal nerve, inhibits the release of pro-inflammatory neuropeptides such as calcitonin gene-related peptide (CGRP) and substance P. By suppressing this neuropeptide release, eletriptan disrupts the peripheral sensitization and central transmission of nociceptive signals within the trigeminovascular system, further contributing to pain relief and reduction of associated migraine symptoms like photophobia and phonophobia. The selective nature of eletriptan's receptor profile, with little to no at 5-HT2 receptors or other non-serotonergic receptors (e.g., adrenergic, ), limits its vasoconstrictive effects to cranial vasculature and minimizes risks of systemic cardiovascular side effects observed with first-generation . This targeted action enhances its tolerability while maintaining efficacy for acute treatment.

Pharmacokinetics

Eletriptan is rapidly absorbed after , with a median time to maximum concentration (T_max) of approximately 1.5 hours in healthy subjects and 2.0 hours in patients. The absolute is about 50%. Administration with a high-fat increases the area under the curve () and maximum concentration (C_max) by 20% to 30%, though it may slightly delay T_max without significantly altering overall exposure. The volume of at is approximately 138 L, indicating moderate . Eletriptan is approximately 85% bound to proteins, primarily . Eletriptan undergoes extensive hepatic , primarily via the enzyme through oxidative N-demethylation to form the N-demethyl metabolite, which accounts for 10% to 20% of parent drug concentrations and has similar but less potent pharmacological activity compared to the parent compound. Minor contributions to N-demethylation come from , , and CYP2C19. Other metabolites include the N-oxide and an acetic acid derivative, which are pharmacologically inactive. This profile contributes to potential drug interactions with potent inhibitors. The terminal elimination of eletriptan is approximately 4 hours, with the N-demethyl having a longer of about 13 hours. Total clearance is approximately 36 L/h, with renal clearance accounting for about 10% and non-renal (primarily fecal via biliary excretion) for the remaining 90%. Following , approximately 50% of the dose is recovered in and the rest in , predominantly as metabolites; less than 10% is excreted unchanged in . are linear over the therapeutic dose range, with no accumulation observed upon repeated dosing due to the short .

Chemistry

Chemical Structure and Properties

Eletriptan is a synthetic derivative of , characterized by an ring core substituted at the 3-position with a chiral (2R)-1-methylpyrrolidin-2-ylmethyl group and at the 5-position with a 2-(phenylsulfonyl)ethyl chain. This structure includes key functional groups such as the aromatic system, a moiety (–SO₂–), and a tertiary amine within the N-methylpyrrolidine ring, contributing to its chemical identity as a member of the 3-alkylindole class. The molecular formula of eletriptan is C₂₂H₂₆N₂O₂S, with a of 382.52 g/mol. In its form, it presents as a solid, typically appearing as a pale yellow to dark yellow powder, though the used in formulations is described as an off-white to light tan powder. Eletriptan exhibits limited aqueous , with the soluble at approximately 1.18 mg/L in water, rendering it sparingly soluble; however, the enhances for pharmaceutical applications. It dissolves in organic solvents such as and DMSO. The pKa of the conjugate acid (from the nitrogen) is 8.37, indicating basic character that influences salt formation and behavior. Additionally, its value of 3.9 reflects moderate lipophilicity. The compound demonstrates stability under standard storage conditions, though the hydrobromide salt is recommended to be kept in a dark place under an inert atmosphere and stored below –20°C to maintain integrity. Its melting point for the hydrobromide salt is 169–171°C.

Nomenclature

Eletriptan is the International Nonproprietary Name (INN) assigned to this compound by the World Health Organization. The systematic IUPAC name for eletriptan is 3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole. A common synonym is (R)-3-(1-methylpyrrolidin-2-ylmethyl)-5-(2-phenylsulfonylethyl)-1H-indole. The pharmaceutical salt form is designated as eletriptan . Key chemical identifiers include CID 77993 for the free base, with number 143322-58-1 assigned to the free base and number 177834-92-3 to the hydrobromide salt. Eletriptan is a derivative utilized in pharmaceutical formulations, primarily as the salt.

Development and History

and Clinical Trials

Eletriptan was developed by in the 1990s as a second-generation intended to provide enhanced selectivity for the 5-HT1B/1D receptors compared to the first-generation agent . This design aimed to improve efficacy while minimizing off-target effects associated with broader serotonin receptor affinity. The compound demonstrated approximately six-fold greater affinity for these receptors, supporting its potential for more targeted relief. Pivotal phase III trials in the late 1990s consisted of randomized, double-blind, -controlled studies evaluating eletriptan across multiple attacks. In one multicenter trial involving patients treating moderate to severe attacks, the 40 mg dose achieved 2-hour pain-free rates of 47% when administered early in the attack, significantly superior to (17%). Broader analyses from these trials reported 2-hour pain-free responses ranging from 27% to 47% for the 40 mg dose across various conditions, compared to 4-17% for , establishing its acute efficacy. Long-term trials extended up to one year in patients with frequent , involving open-label of multiple attacks, confirmed good tolerability with profiles consistent with short-term use and no evidence of tolerance development or rebound headaches. Recent studies have further strengthened the evidence base for eletriptan. A 2023 retrospective analysis of over 10 million self-reported attacks from a smartphone application ranked eletriptan highest among for real-world effectiveness, with an of 6.1 for symptom relief compared to . That same year, a from the Headache Registry linked triptan non-response, including to eletriptan, to greater severity, such as higher attack frequency and disability, while noting eletriptan's relatively high responder rates among tested agents. A 2024 network of 137 trials affirmed eletriptan's superior efficacy for 2-hour pain freedom ( 5.19 vs. ) over newer non-triptan agents like and . Ongoing formulation research seeks to optimize delivery for faster onset. In 2023, development of a polymeric buccal for eletriptan demonstrated rapid disintegration (13 seconds) and dissolution (42 seconds), yielding higher peak plasma concentrations (119 ng/mL) and improved compared to oral solutions in pharmacokinetic studies on rabbits.

Regulatory Approvals and Patents

Eletriptan received initial regulatory approval from the () in June 2001 for the acute of with or without in adults. The U.S. () subsequently approved eletriptan on December 26, 2002, also for the acute of with or without in adults. These approvals were based on demonstrating and safety in relieving symptoms, marking eletriptan as a second-generation option. In 2025, the added eletriptan (tablet 40 mg) to its Model List of as a recommended for acute attacks in adults, following review by the 25th Expert Committee on the Selection and Use of Essential Medicines. The primary U.S. patent for eletriptan, US Patent No. 5,545,644 covering the compound, was issued on August 13, 1996, and expired on December 26, 2016, after accounting for regulatory review extensions under the Hatch-Waxman Act. A related formulation patent, US Patent No. 6,110,940, extended protection until August 29, 2017. The expiration of these patents facilitated generic entry into the market, reducing barriers for manufacturers seeking (ANDA) approvals. Following patent expiration, the FDA approved the first generic version of eletriptan hydrobromide tablets in 2017, with launching the 20 mg and 40 mg strengths in August of that year. Subsequent ANDAs were granted post-2020 to additional manufacturers, including tentative approvals starting around 2018 for some applicants pending resolution of any remaining exclusivity issues. As of 2025, the FDA's Paragraph IV Patent Certifications list includes ongoing challenges related to eletriptan formulations, reflecting continued generic competition. Since its initial FDA approval, the prescribing information for eletriptan has undergone minor revisions, with the most recent major label update in September 2013 to refine warnings on drug interactions and cardiovascular risks, but no substantial changes to indications or dosing have occurred. Post-marketing efforts by the FDA and continue to monitor adverse events, ensuring ongoing safety assessments without prompting further label modifications as of November 2025.

Society and Culture

Brand Names

Eletriptan is primarily marketed under the brand name Relpax in several countries, including the , , , the , and various markets. In some and Asian markets, it is available under the alternative brand name Relert. Generic versions are also marketed worldwide as Eletriptan Tablets. Branded formulations of eletriptan are available as 20 and 40 film-coated tablets. Originally developed and marketed by , Relpax in the United States transitioned to following the 2020 merger of Pfizer's division with . Eletriptan is widely available by prescription in the United States, the , , and many developing countries including , , and . In , the 40 formulation is accessible over-the-counter as a pharmacist-only medicine in limited packs, while higher doses remain prescription-only. The availability of generic versions, approved by regulatory agencies such as the FDA, has broadened access globally following the expiration of brand-name exclusivity. Legally, eletriptan is classified as a prescription-only in most jurisdictions worldwide and is not designated as a under international narcotic regulations. In , it falls under of the Drugs and Cosmetics Rules, 1945, mandating sale only with a valid prescription from a registered medical practitioner. Regarding pricing and access, generic eletriptan in the United States typically costs $10–50 per pack of 6–12 tablets as of 2025, depending on dosage and , making it more affordable than the brand-name version. It is included in national formularies such as Australia's , which subsidizes costs for eligible patients. Recent developments include ongoing expansions in generic competition, as reflected in the FDA's Orange Book updates through October 2025, which have further enhanced affordability and .

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