Eletriptan

{{Short description|Chemical compound}} {{Use dmy dates|date=June 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Drugbox | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 459434734 | image = Eletriptan skeletal.svg | width = 250px | image_class = skin-invert-image | image2 = Eletriptan 3D ball-and-stick.png | image_class2 = bg-transparent | width2 = 250px

<!--Clinical data--> | tradename = Relpax, others | Drugs.com = {{drugs.com|monograph|eletriptan-hydrobromide}} | MedlinePlus = a603029 | DailyMedID = Eletriptan | pregnancy_AU = B1 | routes_of_administration = By mouth | class = Serotonin 5-HT_1B, 5-HT_1D, 5-HT_1E, and 5-HT_1F receptor agonist; Triptan; Antimigraine agent | ATC_prefix = N02 | ATC_suffix = CC06 | ATC_supplemental =

<!-- Legal status --> | legal_AU = S3 | legal_AU_comment = & S4 | legal_CA = Rx-only | legal_UK = POM | legal_UK_comment = <ref name="Relpax SmPC">{{cite web | title=Relpax 20mg Film-Coated Tablets. - Summary of Product Characteristics (SmPC) | website=(emc) | date=3 July 2020 | url=https://www.medicines.org.uk/emc/product/1568/smpc | access-date=11 November 2020}}</ref> | legal_US = Rx-only | legal_US_comment = <ref name="Relpax FDA label">{{cite web | title=Relpax- eletriptan hydrobromide tablet, film coated | website=DailyMed | date=10 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=986dc112-b97b-44a3-bfaf-074f906f8bb2 | access-date=11 November 2020}}</ref> | legal_status = Rx-only

<!--Pharmacokinetic data--> | bioavailability = 50%<ref name="Relpax FDA label" /> | protein_bound = | metabolism = Mainly CYP3A4<ref name="Relpax FDA label" /> | elimination_half-life = 4 hours<ref name="Relpax FDA label" /> | excretion =

<!--Identifiers--> | index2_label = HBr | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 143322-58-1 | CAS_number2_Ref = {{cascite|correct|??}} | CAS_number2 = 177834-92-3 | PubChem = 77993 | PubChem2 = 656631 | IUPHAR_ligand = 40 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00216 | DrugBank2_Ref = {{drugbankcite|correct|drugbank}} | DrugBank2 = DBSALT000884 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 70379 | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2 = 570985 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 22QOO9B8KI | UNII2_Ref = {{fdacite|correct|FDA}} | UNII2 = M41W832TA3 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07887 | KEGG2_Ref = {{keggcite|correct|kegg}} | KEGG2 = D01973 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 50922 | ChEBI2_Ref = {{ebicite|correct|EBI}} | ChEBI2 = 61176 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1510 | ChEMBL2_Ref = {{ebicite|correct|EBI}} | ChEMBL2 = 1201003 | synonyms = UK-116044; UK116044

<!--Chemical data--> | IUPAC_name = 3-{[(2''R'')-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1''H''-indole | C=22 | H=26 | N=2 | O=2 | S=1 | SMILES = CN1CCC[C@@H]1Cc3c[nH]c4ccc(CCS(=O)(=O)c2ccccc2)cc34 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PWVXXGRKLHYWKM-LJQANCHMSA-N }}

'''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.<ref name="Relpax FDA label" /><ref name="pmid25624770">{{cite journal | vauthors = Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E | title = A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine | journal = International Journal of General Medicine | volume = 8 | issue = | pages = 27–36 | date = 2015 | pmid = 25624770 | pmc = 4296958 | doi = 10.2147/IJGM.S73673 | doi-access = free }}</ref><ref name="pmid27582896">{{cite journal | vauthors = Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, Martelletti P | title = Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response | journal = Therapeutic Advances in Neurological Disorders | volume = 9 | issue = 5 | pages = 414–23 | date = September 2016 | pmid = 27582896 | pmc = 4994780 | doi = 10.1177/1756285616650619 }}</ref> It is used as an abortive medication, blocking a migraine attack which is already in progress.<ref name="Relpax FDA label" /> Eletriptan is marketed and manufactured by Pfizer.<ref name="Relpax FDA label" />

Eletriptan is a therapeutic alternative on the World Health Organization's List of Essential Medicines.<ref name="WHO24th">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list | year = 2025 | hdl = 10665/382243 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | doi = 10.2471/B09474 | hdl-access=free }}</ref>

==Medical uses== 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.<ref name=accessdata>{{cite web | title=Drug Approval Package: Relpax (Eletriptan) NDA #021016 | website=U.S. Food and Drug Administration (FDA) | date=4 April 2002 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21016_Relpax.cfm | archive-url=https://web.archive.org/web/20201112185232/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21016_Relpax.cfm | url-status=dead | archive-date=12 November 2020 | access-date=11 November 2020}}</ref><ref name="Relpax FDA label" /> 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.<ref name="Relpax FDA label" /> It is available in 20&nbsp;mg and 40&nbsp;mg strengths.<ref name="Relpax FDA label" />

==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.<ref name="Relpax FDA label" /> This is due to the unusual side effect of coronary vasoconstriction due to serotonin 5-HT_1B receptor agonism, which can precipitate a heart attack in those already at risk.<ref name="Relpax FDA label" /> It is also contraindicated in severe kidney (renal) or liver (hepatic) impairment due to its extensive liver metabolism through CYP3A4.<ref name="AC" /><ref name="Relpax FDA label" />

==Side effects== Common side effects include hypertension, tachycardia, headache, dizziness, drowsiness, and symptoms similar to angina pectoris.<ref name="Relpax FDA label" /> Severe allergic reactions have been seen rarely.<ref name="AC">{{cite book|title=Austria-Codex| veditors = Jasek W |publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=62nd|isbn=978-3-85200-181-4|pages=6984–8|language=German}}</ref><ref name="Relpax FDA label" />

==Interactions== 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.<ref name="Relpax FDA label" /> Ergot alkaloids, such as dihydroergotamine, add to the drug's hypertensive effect and should be separated by at least 24 hours.<ref name="AC" /><ref name="Relpax FDA label" />

==Pharmacology== ===Mechanism of action=== {{See also|Triptan#Mechanism of action}} {| class="wikitable floatleft" style="font-size:small;" |+ {{Nowrap|Eletriptan activities}} |- ! Target !! Affinity (K_i, nM) |- | 5-HT_1A || 1.9–45 (K_i)<br />417–1,820 ({{Abbrlink|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_1B || 0.52–15.1 (K_i)<br />8.1–60 ({{Abbr|EC₅₀|half-maximal effective concentration}})<br />83% ({{Abbrlink|E_max|maximal efficacy}}) |- | 5-HT_1D || 0.10–1.5 (K_i)<br />0.63–0.91 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_1E || 40–62 (K_i)<br />30–126 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_1F || 5–20 (K_i)<br />7.4–132 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_2A || 1,150–>3,160 (K_i)<br />851 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_2B || 447 (K_i)<br />155 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT_2C || >3,160 (K_i)<br />{{Abbr|ND|No data}} ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | 5-HT₃ || >3,160 (mouse) |- | 5-HT₄ || >3,160 (guinea pig) |- | 5-HT_5A || 977–1,584 (rat) |- | 5-HT₆ || 525 |- | 5-HT₇ || 200 (K_i)<br />355 ({{Abbr|EC₅₀|half-maximal effective concentration}}) |- | α_1A–α_1D || {{Abbr|ND|No data}} |- | α_2A–α_2C || {{Abbr|ND|No data}} |- | β₁–β₃ || {{Abbr|ND|No data}} |- | D₁–D₅ || {{Abbr|ND|No data}} |- | H₁–H₄ || {{Abbr|ND|No data}} |- | M₁–M₅ || {{Abbr|ND|No data}} |- | I₁, I₂ || {{Abbr|ND|No data}} |- | σ₁, σ₂ || {{Abbr|ND|No data}} |- | {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || {{Abbr|ND|No data}} |- | {{Abbrlink|SERT|Serotonin transporter}} || {{Abbr|ND|No data}} |- | {{Abbrlink|NET|Norepinephrine transporter}} || {{Abbr|ND|No data}} |- | {{Abbrlink|DAT|Dopamine transporter}} || {{Abbr|ND|No data}} |- class="sortbottom" | colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BDBM50103594 CHEBI:50922::Eletriptan::UK-116044::UK-116044-04::UK-116044-04 [As Hydrobromide) | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50103594 | access-date=19 July 2025}}</ref><ref name="DeVriesVillalónSaxena1999">{{cite journal | vauthors = De Vries P, Villalón CM, Saxena PR | title=Pharmacology of triptans | journal=Emerging Drugs | volume=4 | issue=1 | date=1999 | issn=1361-9195 | doi=10.1517/14728214.4.1.107 | pages=107–125 }}</ref><ref name="Tfelt-HansenDeVriesSaxena2000">{{cite journal | vauthors = Tfelt-Hansen P, De Vries P, Saxena PR | title = Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy | journal = Drugs | volume = 60 | issue = 6 | pages = 1259–1287 | date = December 2000 | pmid = 11152011 | doi = 10.2165/00003495-200060060-00003 }}</ref><ref name="SaxenaTfelt-Hansen2001">{{cite journal | vauthors = Saxena PR, Tfelt-Hansen P | title=Success and failure of triptans | journal=The Journal of Headache and Pain | volume=2 | issue=1 | date=2001 | issn=1129-2369 | pmc=3611827 | doi=10.1007/s101940170040 | doi-access=free | pages=3–11 }}</ref><ref name="Brink1999">{{cite web | vauthors = van den Brink M | title=Coronary Side Effects of Antimigraine Drugs From Patient to Receptor | website= RePub, Erasmus University Repository | date=22 December 1999 | url=https://repub.eur.nl/pub/16171/ | access-date=19 June 2025 | quote = Table 1.2 Receptor binding properties (pKi values) of sumatriptan and second-generation triptans at 5-HT receptors. [...]}}</ref><ref name="DeleuHanssens2000">{{cite journal | vauthors = Deleu D, Hanssens Y | title = Current and emerging second-generation triptans in acute migraine therapy: a comparative review | journal = J Clin Pharmacol | volume = 40 | issue = 7 | pages = 687–700 | date = July 2000 | pmid = 10883409 | doi = 10.1177/00912700022009431 | url = }}</ref><ref name="ColeRabasseda2001">{{cite journal | vauthors = Cole P, Rabasseda X | title = Migraine headache treatment with eletriptan, a second-generation serotonin receptor agonist | journal = Drugs Today (Barc) | volume = 37 | issue = 3 | pages = 159–171 | date = March 2001 | pmid = 12783088 | doi = 10.1358/dot.2001.37.3.614851 | url = }}</ref><ref name="Broek2002">{{cite web | vauthors = van den Broek RW | title=Vascular Effects of Antimigraine Drugs: pharmacology of human in vitro models in migraine | website= RePub, Erasmus University Repository | date=13 March 2002 | url=https://repub.eur.nl/pub/16167/ | access-date=19 June 2025 | quote=Table 1.2 Receptor binding properties (pKi values) of the triptans at human 5-HT receptors. [...]}}</ref><br /><ref name="Rubio-BeltránLabastida-RamírezHaanes2019">{{cite journal | vauthors = Rubio-Beltrán E, Labastida-Ramírez A, Haanes KA, van den Bogaerdt A, Bogers AJ, Zanelli E, Meeus L, Danser AH, Gralinski MR, Senese PB, Johnson KW, Kovalchin J, Villalón CM, MaassenVanDenBrink A | title = Characterization of binding, functional activity, and contractile responses of the selective 5-HT_1F receptor agonist lasmiditan | journal = British Journal of Pharmacology | volume = 176 | issue = 24 | pages = 4681–4695 | date = December 2019 | pmid = 31418454 | pmc = 6965684 | doi = 10.1111/bph.14832 | quote = TABLE 1 Summary of pIC50 (negative logarithm of the molar concentration of these compounds at which 50% of the radioligand is displaced) and pKi (negative logarithm of the molar concentration of the Ki ) values of individual antimigraine drugs at 5‐HT receptors [...] TABLE 2 Summary of pEC50 values of cAMP (5‐HT1A/B/E/F and 5‐HT7), GTPγS (5‐HT1A/B/D/E/F), and IP (5‐HT2) assays of individual antimigraine drugs at 5‐HT receptors [...] }}</ref><ref name="PerezHalazyPauwels1999">{{cite journal | author=Perez, M. | author2=Halazy, S. | author3=Pauwels, P.J. | author4=Colpaert, F.C. | author5=John, G.W. | title=F-11356 | journal=Drugs of the Future | volume=24 | issue=6 | date=1999 | doi=10.1358/dof.1999.024.06.537284 | page=0605 | url=http://access.portico.org/stable?au=pjbf78x6c9d | access-date=23 June 2025| url-access=subscription }}</ref><ref name="MitsikostasWard2024">{{cite book | vauthors = Mitsikostas DD, Ward TN | title = Migraine Management | chapter = Evidence-based symptomatic treatment of migraine | series = Handbook of Clinical Neurology | volume = 199 | pages = 203–218 | date = 2024 | pmid = 38307647 | doi = 10.1016/B978-0-12-823357-3.00004-5 | isbn = 978-0-12-823357-3 }}</ref><ref name="Comer2002">{{cite journal | vauthors = Comer MB | title = Pharmacology of the selective 5-HT(1B/1D) agonist frovatriptan | journal = Headache | volume = 42 | issue = Suppl 2 | pages = S47–S53 | date = April 2002 | pmid = 12028320 | doi = 10.1046/j.1526-4610.42.s2.2.x }}</ref> |}

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.<ref name="Relpax FDA label" /> Eletriptan binds with high affinity to the [[5-HT1B|5-HT_[1B]]_, _1D_, [[5-HT1F|_1F]]] receptors. It has a modest affinity to the [[5-HT1A|5-HT_[1A]]_, _1E_, _2B_, [[5-HT7|_7]]] receptors, and little to no affinity at the [[5-HT2A|5-HT_[2A]]_, _2C_, ₃_, ₄_, _5A_, [[5-HT6|_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-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-HT_2A receptor agonist ({{Abbrlink|EC₅₀|half-maximal effective concentration}} = 851{{nbsp}}nM), albeit with about two to three orders of magnitude lower activational potency than at the serotonin 5-HT_1B and 5-HT_1D receptors.<ref name="Rubio-BeltránLabastida-RamírezHaanes2019">{{cite journal | vauthors = Rubio-Beltrán E, Labastida-Ramírez A, Haanes KA, van den Bogaerdt A, Bogers AJ, Zanelli E, Meeus L, Danser AH, Gralinski MR, Senese PB, Johnson KW, Kovalchin J, Villalón CM, MaassenVanDenBrink A | title = Characterization of binding, functional activity, and contractile responses of the selective 5-HT_1F receptor agonist lasmiditan | journal = British Journal of Pharmacology | volume = 176 | issue = 24 | pages = 4681–4695 | date = December 2019 | pmid = 31418454 | pmc = 6965684 | doi = 10.1111/bph.14832 | quote = TABLE 1 Summary of pIC50 (negative logarithm of the molar concentration of these compounds at which 50% of the radioligand is displaced) and pKi (negative logarithm of the molar concentration of the Ki ) values of individual antimigraine drugs at 5‐HT receptors [...] TABLE 2 Summary of pEC50 values of cAMP (5‐HT1A/B/E/F and 5‐HT7), GTPγS (5‐HT1A/B/D/E/F), and IP (5‐HT2) assays of individual antimigraine drugs at 5‐HT receptors [...] }}</ref>

==Chemistry== Eletriptan is a tryptamine and pyrrolidinylmethylindole derivative and is a 5-substituted and cyclized tryptamine derivative of the psychedelic drug dimethyltryptamine (DMT).<ref name="PubChem" />

The experimental log P is 3.9 and its predicted log P is 1.78 to 4.1.<ref name="TekesSzegiHashemi2013">{{cite journal | vauthors = Tekes K, Szegi P, Hashemi F, Laufer R, Kalász H, Siddiq A, Ertsey C | title = Medicinal chemistry of antimigraine drugs | journal = Curr Med Chem | volume = 20 | issue = 26 | pages = 3300–3316 | date = 2013 | pmid = 23746273 | doi = 10.2174/0929867311320260012 | url = }}</ref><ref name="PubChem">{{cite web | title=Eletriptan | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/77993 | access-date=27 June 2025}}</ref><ref name="DrugBank">{{cite web | title=Eletriptan: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 July 2019 | url=https://go.drugbank.com/drugs/DB00216 | access-date=27 June 2025}}</ref>

===Additional chemical names=== * Merck Index: 3-[[(2''R'')-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

==History== Eletriptan was approved for medical use in the United States in 2002.<ref name="Relpax FDA label" /> It was covered by {{US patent|5545644|U.S. Patent no. 5545644}}<ref name=accessdata/><ref>{{US patent|5545644|U.S. Patent no. 5545644}}, John E. Macor & Martin J. Wythes, ''Indole Derivatives'', 13 August 1996.</ref> and {{US patent|6110940|U.S. Patent no. 6110940}};<ref name=accessdata/><ref>{{US patent|6110940|U.S. Patent no. 6110940}}, Valerie Denise Harding, ''et al.'', ''Salts of an anti-migraine indole derivative'', 29 August 2000.</ref> both now expired.

==Society and culture== ===Brand names=== Eletriptan is sold in the United States, Canada, Australia, and the United Kingdom under the brand name Relpax,<ref name="Relpax FDA label" /><ref>{{cite web | title=Relpax Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=74152 | access-date=11 November 2020}}</ref><ref name="Relpax SmPC" /> and in several other countries under the brand name Relert.{{cn|date=October 2020}}

In the United States, Relpax is marketed by Viatris after Upjohn was spun off from Pfizer.<ref>{{cite web | title=Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan | publisher=Pfizer | via=Business Wire | date=16 November 2020 | url=https://www.businesswire.com/news/home/20201116005378/en/ | access-date=17 June 2024}}</ref><ref>{{cite web | title=Relpax | website=Pfizer | url=https://www.pfizer.com/products/product-detail/relpax | access-date=17 June 2024}}</ref><ref>{{cite web | title=Brands | website=Viatris | date=16 November 2020 | url=https://www.viatris.com/en/products/brands | access-date=17 June 2024}}</ref>

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/6423 Eletriptan - Isomer Design]

{{Antimigraine preparations}} {{Serotonin receptor modulators}} {{Tryptamines}} {{Portal bar | Medicine}} {{Authority control}}

Category:5-HT1B agonists Category:5-HT1D agonists Category:5-HT1E agonists Category:5-HT1F agonists Category:5-HT2A agonists Category:5-HT7 agonists Category:Benzosulfones Category:N,N-Dialkyltryptamines Category:Drugs developed by Pfizer Category:Pyrrolidinylmethylindoles Category:Triptans Category:World Health Organization essential medicines