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{{Short description|Chemical compound}}
{{Refimprove|date=March 2010}}
{{Refimprove|date=March 2010}}
{{Use dmy dates|date=June 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 459434734
| verifiedrevid = 459434734
⚫
| IUPAC_name = (''R'')-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole
| image = Eletriptan skeletal.svg
| image = Eletriptan skeletal.svg
| image2 = Eletriptan 3D ball-and-stick.png
| image2 = Eletriptan 3D ball-and-stick.png

<!--Clinical data-->
<!--Clinical data-->
| tradename = Relpax
| tradename = Relpax, Relert
| Drugs.com = {{drugs.com|monograph|relpax}}
| Drugs.com = {{drugs.com|monograph|eletriptan-hydrobromide}}
| MedlinePlus = a603029
| MedlinePlus = a603029
| DailyMedID = Eletriptan
| pregnancy_AU = B1
| pregnancy_US = C
| pregnancy_US = C
⚫
| routes_of_administration = [[Oral administration|By mouth]]
⚫
| ATC_prefix = N02
⚫
| ATC_suffix = CC06
⚫
| ATC_supplemental =

| legal_AU = 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
| legal_status = Rx-only

⚫
| routes_of_administration = oral
<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = 50%
| bioavailability = 50%
Line 20: Line 36:
| elimination_half-life = 4 hours
| elimination_half-life = 4 hours
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| index2_label = HBr
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 143322-58-1
| CAS_number = 143322-58-1
| CAS_number2_Ref = {{cascite|correct|??}}
⚫
| ATC_prefix = N02
| CAS_number2 = 177834-92-3
⚫
| ATC_suffix = CC06
⚫
| ATC_supplemental =
| PubChem = 77993
| PubChem = 77993
| PubChem2 = 656631
| IUPHAR_ligand = 40
| IUPHAR_ligand = 40
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00216
| DrugBank = DB00216
| DrugBank2_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank2 = DBSALT000884
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 70379
| ChemSpiderID = 70379
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2 = 570985
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 22QOO9B8KI
| UNII = 22QOO9B8KI
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = M41W832TA3
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01973
| KEGG = D07887
| KEGG2_Ref = {{keggcite|changed|kegg}}
| KEGG2 = D01973
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50922
| ChEBI = 50922
| ChEBI2_Ref = {{ebicite|correct|EBI}}
| ChEBI2 = 61176
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1510
| ChEMBL = 1510
| ChEMBL2_Ref = {{ebicite|correct|EBI}}
| ChEMBL2 = 1201003

<!--Chemical data-->
<!--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
| C=22 | H=26 | N=2 | O=2 | S=1
| smiles = CN1CCC[C@@H]1Cc3c[nH]c4ccc(CCS(=O)(=O)c2ccccc2)cc34
| molecular_weight = 382.52 g/mol
| smiles = O=S(=O)(c1ccccc1)CCc4ccc2c(c(cn2)C[C@@H]3N(C)CCC3)c4
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|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,5-6,11-137T56T
| 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,5-6,11-137T56T
Line 50: Line 81:
}}
}}


'''Eletriptan''' (trade name '''Relpax''', used in the form of eletriptan hydrobromide) is a second generation [[triptan]] [[medication|drug]] intended for treatment of [[migraine]] [[headache]]s. It is used as an [[abortive medication]], blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by [[Pfizer|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''', 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]] [[headache]]s.<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. Eletriptan is marketed and manufactured by [[Pfizer|Pfizer Inc]].


==Approval and availability==
==Approval and availability==
Eletriptan was approved by the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) on December 26, 2002, for the acute treatment of migraine with or without [[Aura (symptom)|aura]] in adults.<ref name=accessdata>FDA AccessData entry for [http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=020763&TABLE1=OB_Rx Eletriptan Hydrobromide], accessed March 10, 2010.</ref> It is available only by [[Medical prescription|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&nbsp;mg and 40&nbsp;mg strengths.
Eletriptan was approved by the US [[Food and Drug Administration]] (FDA) in December 2002, for the acute treatment of migraine with or without [[Aura (symptom)|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 | access-date=11 November 2020}}</ref> It is available only by [[Medical prescription|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&nbsp;mg and 40&nbsp;mg strengths. But unfortunately due to unknown reasons this product is hardly available in Germany if at all.


Eletriptan is 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'', August 13, 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'', August 29, 2000.</ref> the FDA lists the patents as scheduled for expiration on December 26, 2016, and August 29, 2017, respectively.<ref name=accessdata/>
Eletriptan 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.


==Mechanism of action==
==Mechanism of action==
{{further|Serotonin receptor agonist|Triptan#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 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 receptor|5-HT<sub>1</sub> family receptor]]s. Eletriptan binds with high affinity to the [[5-HT1B|5-HT<sub>[1B</sub>]]<sub>,</sub> [[5-HT1D|<sub>1D</sub>]]<sub>,</sub> [[5-HT1F|<sub>1F]</sub>]] receptors. It has a modest affinity to the [[5-HT1A|5-HT<sub>[1A</sub>]]<sub>,</sub> [[5-HT1E|<sub>1E</sub>]]<sub>,</sub> [[5-HT2B receptor|<sub>2B</sub>]]<sub>,</sub> [[5-HT7|<sub>7]</sub>]] receptors, and little to no affinity at the [[5-HT2A|5-HT<sub>[2A</sub>]]<sub>,</sub> [[5-HT2C receptor|<sub>2C</sub>]]<sub>,</sub> [[5-HT3|<sub>3</sub>]]<sub>,</sub> [[5-HT4|<sub>4</sub>]]<sub>,</sub> [[5-HT5A|<sub>5A</sub>]]<sub>,</sub> [[5-HT6|<sub>6]</sub>]] receptors.
Eletriptan is a [[serotonin receptor agonist]], specifically an [[agonist]] of certain [[5-HT1 receptor|5-HT<sub>1</sub> family receptor]]s. Eletriptan binds with high affinity to the [[5-HT1B|5-HT<sub>[1B</sub>]]<sub>,</sub> [[5-HT1D|<sub>1D</sub>]]<sub>,</sub> [[5-HT1F|<sub>1F]</sub>]] receptors. It has a modest affinity to the [[5-HT1A|5-HT<sub>[1A</sub>]]<sub>,</sub> [[5-HT1E|<sub>1E</sub>]]<sub>,</sub> [[5-HT2B receptor|<sub>2B</sub>]]<sub>,</sub> [[5-HT7|<sub>7]</sub>]] receptors, and little to no affinity at the [[5-HT2A|5-HT<sub>[2A</sub>]]<sub>,</sub> [[5-HT2C receptor|<sub>2C</sub>]]<sub>,</sub> [[5-HT3|<sub>3</sub>]]<sub>,</sub> [[5-HT4|<sub>4</sub>]]<sub>,</sub> [[5-HT5A|<sub>5A</sub>]]<sub>,</sub> [[5-HT6|<sub>6]</sub>]] receptors.


Eletriptan has no significant affinity or pharmacological activity at [[adrenergic receptor|adrenergic]] [[alpha-1 adrenergic receptor|α<sub>1</sub>]], [[alpha-2 adrenergic receptor|α<sub>2</sub>]], or [[beta-adrenergic receptor|β]]; [[dopamine receptor|dopaminergic]] [[D1 receptor|D<sub>1</sub>]] or [[D2 receptor|D<sub>2</sub>]]; [[muscarinic acetylcholine receptor|muscarinic]]; or [[opioid receptor]]s. 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).
Eletriptan has no significant affinity or pharmacological activity at [[adrenergic receptor|adrenergic]] [[alpha-1 adrenergic receptor|α<sub>1</sub>]], [[alpha-2 adrenergic receptor|α<sub>2</sub>]], or [[beta-adrenergic receptor|β]]; [[dopamine receptor|dopaminergic]] [[D1 receptor|D<sub>1</sub>]] or [[D2 receptor|D<sub>2</sub>]]; [[muscarinic acetylcholine receptor|muscarinic]]; or [[opioid receptor]]s. 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-HT<sub>1</sub> receptor agonists in migraine. One theory suggests that activation of 5-HT<sub>1</sub> 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-HT<sub>1</sub> receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
Two theories have been proposed to explain the efficacy of 5-HT<sub>1</sub> receptor agonists in migraine. One theory suggests that activation of 5-HT<sub>1</sub> 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-HT<sub>1</sub> receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.


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


==Contraindications==
==Contraindications==
Line 73: Line 105:


==Interactions==
==Interactions==
Strong inhibitors of the liver enzyme CYP3A4, such as [[erythromycin]] and [[ketoconazole]], significantly increase blood plasma concentration and of eletriptan and should be separated by at least 72 hours. [[Ergot alkaloid]]s, such as [[dihydroergotamine]], add to the drug's hypertensive effect and should be separated by at least 24 hours.<ref name="AC" />
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 alkaloid]]s, such as [[dihydroergotamine]], add to the drug's hypertensive effect and should be separated by at least 24 hours.<ref name="AC" />


==Additional chemical names==
==Additional chemical names==
Line 79: Line 111:
* 5-[2-(benzenesulfonyl)ethyl]-3-(1-methylpyrrolidin-2(''R'')-ylmethyl)-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
* (''R'')-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

== Society and culture ==
=== Brand names ===
It 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 US, 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==
==References==
{{Reflist}}
{{Reflist}}


{{Serotonin receptor modulators}}
==External links==
* [http://129.128.185.122/drugbank2/drugs/DB00216/fda_labels/990 FDA label] (December 2002)
* [[Physicians' Desk Reference]] entry for [http://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=rel1663.html&contentName=Relpax&contentId=649 ''Relpax'']
* [[Medline]] Plus Drug Information for [http://www.nlm.nih.gov/medlineplus/druginfo/meds/a603029.html Eletriptan]
* Pfizer [http://www.relpax.com Relpax site]

{{Serotonergics}}
{{Triptans}}
{{Triptans}}
{{Tryptamines}}
{{Portal bar | Medicine}}


[[Category:5-HT1D agonists]]
[[Category:5-HT1E agonists]]
[[Category:5-HT1F agonists]]
[[Category:Triptans]]
[[Category:Triptans]]
[[Category:Pfizer products]]
[[Category:Drugs developed by Pfizer]]
[[Category:Pyrrolidines]]
[[Category:Pyrrolidines]]
[[Category:Sulfones]]
[[Category:Benzosulfones]]
[[Category:5-HT1D agonists]]
[[Category:Tryptamines]]

Latest revision as of 12:33, 30 November 2024

Eletriptan
Clinical data
Trade namesRelpax, Relert
AHFS/Drugs.comMonograph
MedlinePlusa603029
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability50%
MetabolismCYP3A4
Elimination half-life4 hours
Identifiers
  • 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.337 Edit this at Wikidata
Chemical and physical data
FormulaC22H26N2O2S
Molar mass382.52 g·mol−1
3D model (JSmol)
  • CN1CCC[C@@H]1Cc3c[nH]c4ccc(CCS(=O)(=O)c2ccccc2)cc34
  • 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 checkY
 ☒NcheckY (what is this?)  (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.[3][4] It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc.

Approval and availability

[edit]

Eletriptan was approved by the US Food and Drug Administration (FDA) in December 2002, for the acute treatment of migraine with or without aura in adults.[5] 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 and 40 mg strengths. But unfortunately due to unknown reasons this product is hardly available in Germany if at all.

Eletriptan was covered by U.S. Patent no. 5545644[5][6] and U.S. Patent no. 6110940;[5][7] both now expired.

Mechanism of action

[edit]
Further information: Serotonin receptor agonist and Triptan § 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-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.

Side effects

[edit]

Common side effects include hypertension, tachycardia, headache, dizziness, drowsiness and symptoms similar to angina pectoris. Severe allergic reactions are rare.[8]

Contraindications

[edit]

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 5HT1B antagonism, which can precipitate a heart attack in those already at risk. It is also contraindicated in severe renal or hepatic impairment due to its extensive liver metabolism through CYP3A4.[8]

Interactions

[edit]

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.[8]

Additional chemical names

[edit]
  • 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

Society and culture

[edit]

Brand names

[edit]

It is sold in the United States, Canada, Australia, and the United Kingdom under the brand name Relpax,[2][9][1] and in several other countries under the brand name Relert.[citation needed]

In the US, Relpax is marketed by Viatris after Upjohn was spun off from Pfizer.[10][11][12]

References

[edit]
  1. ^ a b "Relpax 20mg Film-Coated Tablets. - Summary of Product Characteristics (SmPC)". (emc). 3 July 2020. Retrieved 11 November 2020.
  2. ^ a b "Relpax- eletriptan hydrobromide tablet, film coated". DailyMed. 10 December 2019. Retrieved 11 November 2020.
  3. ^ Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E (2015). "A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine". International Journal of General Medicine. 8: 27–36. doi:10.2147/IJGM.S73673. PMC 4296958. PMID 25624770.
  4. ^ Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, et al. (September 2016). "Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response". Therapeutic Advances in Neurological Disorders. 9 (5): 414–23. doi:10.1177/1756285616650619. PMC 4994780. PMID 27582896.
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  6. ^ U.S. Patent no. 5545644, John E. Macor & Martin J. Wythes, Indole Derivatives, 13 August 1996.
  7. ^ U.S. Patent no. 6110940, Valerie Denise Harding, et al., Salts of an anti-migraine indole derivative, 29 August 2000.
  8. ^ 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.
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