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| Systematic (IUPAC) name | |
|---|---|
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(R)-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole
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| Clinical data | |
| Trade names | Relpax |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a603029 |
| Pregnancy category |
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| Legal status |
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| Routes of administration |
oral |
| Pharmacokinetic data | |
| Bioavailability | 50% |
| Metabolism | CYP3A4 |
| Biological half-life | 4 hours |
| Identifiers | |
| CAS Registry Number | 143322-58-1 Y |
| ATC code | N02CC06 |
| 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 |
| Chemical data | |
| Formula | C22H26N2O2S |
| Molecular mass | 382.52 g/mol |
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SMILES
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| N (what is this?) (verify) | |
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.
Contents
- 1 Approval and availability
- 2 Mechanism of action
- 3 Side effects
- 4 Contraindications
- 5 Interactions
- 6 Additional chemical names
- 7 Synthesis
- 8 References
- 9 External links
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, 40 mg and 80 mg strengths.
Eletriptan is covered by U.S. Patent no. 5545644[1][2] and U.S. Patent no. 6110940;[1][3] the FDA lists the patents as scheduled for expiration on December 26, 2016, and August 29, 2017, respectively.[1]
Mechanism of action
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.
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-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-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.
Side effects
Common side effects include hypertension, tachycardia, headache, dizzyness, and symptoms similar to angina pectoris. Severe allergic reactions are rare.[4]
Contraindications
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. It is also contraindicated in severe renal or hepatic impairment.[4]
Interactions
The drug has a relatively low potential for interactions. Notably, it is unlikely to interact to a relevant extent with beta blockers, tricyclic antidepressants and SSRI type antidepressants. Strong inhibitors of the liver enzyme CYP3A4, such as erythromycin and ketoconazole, significantly increase blood plasma concentrations and half life of eletriptan. Ergot alkaloids add to the drug's hypertensive effect.[4]
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
Synthesis
Eletriptan synthesis: U.S. Patent 5,545,644
References
- ^ a b c d FDA AccessData entry for Eletriptan Hydrobromide, accessed March 10, 2010.
- ^ U.S. Patent no. 5545644, John E. Macor & Martin J. Wythes, Indole Derivatives, August 13, 1996.
- ^ U.S. Patent no. 6110940, Valerie Denise Harding, et al., Salts of an anti-migraine indole derivative, August 29, 2000.
- ^ a b c Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 6984–8. ISBN 978-3-85200-181-4.
External links
- FDA label (December 2002)
- Physicians' Desk Reference entry for Relpax
- Medline Plus Drug Information for Eletriptan
- Pfizer Relpax site
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UpToDate Contents
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- 1. 成人における片頭痛の急性期治療 acute treatment of migraine in adults
- 2. 性行為に伴う一次性頭痛 primary headache associated with sexual activity
- 3. 患者情報：成人における片頭痛（詳細） migraine headaches in adults beyond the basics
- 4. 患者情報：思春期のうつ病の治療選択肢（詳細） depression treatment options for adolescents beyond the basics
- 5. 患者情報：成人における頭痛の治療（詳細） headache treatment in adults beyond the basics
English Journal
- Comparative efficacy of triptans for the abortive treatment of migraine: A multiple treatment comparison meta-analysis.
- Thorlund K, Mills EJ, Wu P, Ramos E, Chatterjee A, Druyts E, Goadsby PJ.SourceDepartment of Clinical Epidemiology & Biostatistics, McMaster University, Canada.
- Cephalalgia : an international journal of headache.Cephalalgia.2013 Oct 9. [Epub ahead of print]
- BACKGROUND: Migraine is the most common neurological condition in developed countries. The abortive treatment of migraine attacks is important both for quality of life and costs associated with illness. Triptans, serotonin 5-HT1B/1D receptor agonists, effectively relieve the pain, disability, and as
- PMID 24108308
- α-[11C] methyl-L tryptophan-PET as a surrogate for interictal cerebral serotonin synthesis in migraine without aura.
- Sakai Y, Nishikawa M, Diksic M, Aubé M.SourceMontreal Neurological Institute, and Department of Neurology and Neurosurgery, McGill University, Canada.
- Cephalalgia : an international journal of headache.Cephalalgia.2013 Sep 20. [Epub ahead of print]
- BACKGROUND: Alteration in central serotonin biology has been implicated in migraine, and serotonin (5-HT) agonists have been available for more than a decade in the treatment of that condition.OBJECTIVES: To test this hypothesis, we studied in vivo using positron-emission tomography (PET) and α-[1
- PMID 24057438
- Consistency of eletriptan in treating migraine: Results of a randomized, within-patient multiple-dose study.
- Almas M, Tepper SJ, Landy S, Schweizer E, Ramos E.SourcePfizer Inc., New York, NY, USA.
- Cephalalgia : an international journal of headache.Cephalalgia.2013 Aug 30. [Epub ahead of print]
- OBJECTIVE: The current study evaluated the consistency of eletriptan response.METHODS: Using a within-patient crossover design, patients with migraine completed a three-attack, open-label, lead-in period, before being treated, double-blind for four attacks, with either eletriptan 40 mg (ELE-40; N
- PMID 23946318
Japanese Journal
- 片頭痛治療薬エレトリプタン(レルパックス^【〇!R】) の薬理学的,薬物動態学的および臨床学的特徴
- 表 雅之
- 日本薬理学雑誌 122(1), 93-101, 2003-07-01
- エレトリプタン（レルパックス®）は，トリプタン系と呼ばれる新しいタイプの片頭痛治療薬である．エレトリプタンは，5-HT1B/1D受容体の活性化を介して，頭蓋血管を収縮させ，また，三叉神経からのニューロペプチドの遊離を抑制することにより，痛みの中枢への伝導を減少させると考えられている．エレトリプタンは，ヒト5-HT1B/1D受容体に対して選択的な親和性と強力なアゴニスト作用を示し，冠動脈と …
- NAID 10011598695
Related Links
- Suffering from migraine headaches? Learn how RELPAX® (eletriptan HBr) provides migraine treatment and pain relief, and find the risks & benefits of RELPAX®. ... By using the RELPAX $10 Co-pay Card, you acknowledge that you ...
- Relpax (eletriptan) is used to relieve migraine pain and symptoms, such as nausea and sensitivity to light and sound. Includes Relpax side effects, interactions and indications. ... Relpax side effects Get emergency medical help if ...
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