View source for Rizatriptan

{{Short description|Medication used for the treatment of migraine headaches}}
{{Use dmy dates|date=December 2023}}
{{Cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
| Verifiedfields     = changed
| Watchedfields      = changed
| verifiedrevid      = 464382941
| image              = Rizatriptan Structural Formula V.1.svg
| alt                = 
| image2             = Rizatriptan 3D ball-and-stick.png
| alt2               = 

<!-- Clinical data -->
| tradename          = Maxalt, Maxalt-MLT, Rizafilm, others
| Drugs.com          = {{drugs.com|monograph|rizatriptan-benzoate}}
| MedlinePlus        = a601109
| DailyMedID         = Rizatriptan
| pregnancy_AU       = B1
| pregnancy_AU_comment = 
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]]
| class              = [[Triptan]]
| ATC_prefix         = N02
| ATC_suffix         = CC04
| ATC_supplemental   = 

<!-- Legal status -->
| legal_AU           = S4
| legal_AU_comment   = /&nbsp;S3
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment  = 
| legal_CA           = Rx-only
| legal_CA_comment  = 
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  = 
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  = 
| legal_UK          = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment  = 
| legal_US          = Rx-only
| legal_US_comment  = <ref name="Maxalt FDA label">{{cite web | title=Maxalt- rizatriptan benzoate tablet; Maxalt-MLT- rizatriptan benzoate tablet, orally disintegrating | website=DailyMed | date=1 June 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=007b4644-e0e7-4863-9ae3-fe09676b3f5f | access-date=25 December 2023 | archive-date=23 March 2023 | archive-url=https://web.archive.org/web/20230323070601/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=007b4644-e0e7-4863-9ae3-fe09676b3f5f | url-status=live }}</ref><ref name="Rizafilm FDA label">{{Cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/205394s000lbl.pdf |title=Archived copy |access-date=25 December 2023 |archive-date=2 August 2023 |archive-url=https://web.archive.org/web/20230802162757/https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/205394s000lbl.pdf |url-status=dead }}</ref>
| legal_EU          = 
| legal_EU_comment  = 
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  = 
| legal_status       = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability    = 45%
| protein_bound      = 14%
| metabolism         = By [[monoamine oxidase]]
| elimination_half-life = 2–3 hours
| excretion          = 82% [[urine]]; 12% [[feces]]

<!-- Identifiers -->
| CAS_number_Ref     = {{cascite|correct|??}}
| CAS_number         = 145202-66-0
| PubChem            = 5078
| IUPHAR_ligand      = 51
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB00953
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 4900
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = WR978S7QHH
| KEGG_Ref           = {{keggcite|changed|kegg}}
| KEGG               = D00675
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 48273
| ChEMBL_Ref         = {{ebicite|correct|EBI}}
| ChEMBL             = 905

<!--Chemical data-->
| IUPAC_name         = ''N'',''N''-dimethyl-2-[5-(1''H''-1,2,4-triazol-1-ylmethyl)-1''H''-indol-3-yl]ethanamine
| C                  = 15
| H                  = 19
| N                  = 5
| smiles             = n1cncn1Cc2cc3c(cc2)[nH]cc3CCN(C)C
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C15H19N5/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = ULFRLSNUDGIQQP-UHFFFAOYSA-N
}}

<!-- Definition and medical uses -->
'''Rizatriptan''', sold under the brand name '''Maxalt''' among others, is a [[medication]] used for the treatment of [[migraine headache]]s.<ref name="Maxalt FDA label" /><ref name=AHFS2019/> It is taken [[Oral administration|by mouth]].<ref name="Maxalt FDA label" /><ref name=AHFS2019>{{cite web |title=Rizatriptan Benzoate Monograph for Professionals |url=https://www.drugs.com/monograph/rizatriptan-benzoate.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=18 March 2019 |archive-date=23 October 2020 |archive-url=https://web.archive.org/web/20201023130856/https://www.drugs.com/monograph/rizatriptan-benzoate.html |url-status=live }}</ref> It can also be applied on the tongue.<ref name="Rizafilm FDA label" /> It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).<ref name="Maxalt FDA label" /><ref name="Rizafilm FDA label" />

<!-- Side effects and mechanisms -->
Common side effects include [[chest pain]], dizziness, dry mouth, and tingling.<ref name=AHFS2019/> Other side effects may include [[myocardial infarction]], [[stroke]], [[high blood pressure]], [[serotonin syndrome]], and [[anaphylaxis]].<ref name=AHFS2019/> Excessive use may result in [[medication overuse headache]]s.<ref name=AHFS2019/> Use is not recommended during [[pregnancy]] and [[breastfeeding]] is not recommended within 24 hours after taking a dose.<ref name=BNF76/> Rizatriptan is in the [[triptan]] class and is believed to work by activating the [[5-HT1 receptor|5-HT<sub>1</sub> receptor]].<ref name=AHFS2019/>

<!-- Society and culture -->
Rizatriptan was patented in 1991 and came into medical use in 1998.<ref>{{cite web |title=Drug Approval Package: Maxalt/Rizatritan Benzoate NDA# 20864 & 20865 |publisher=U.S. [[Food and Drug Administration]] (FDA) |date=30 March 2001 |url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20864-20865.cfm |access-date=25 December 2023 |archive-date=6 December 2022 |archive-url=https://web.archive.org/web/20221206085052/https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20864-20865.cfm |url-status=dead }}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title= Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=531 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531 }}</ref> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British National Formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=473|edition=76}}</ref> In 2022, it was the 190th most commonly prescribed medication in the United States, with more than two million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Rizatriptan Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Rizatriptan | access-date = 30 August 2024 }}</ref> Rizatriptan is available in combination with [[meloxicam]] as [[meloxicam/rizatriptan]].

==Medical uses==
Rizatriptan is [[indicated]] to treat acute [[migraine]] attacks with or without [[aura (symptom)|aura]].<ref name="Maxalt FDA label" /><ref name="Rizafilm FDA label" /> It does not prevent future migraine attacks.<ref name="MedlinePlus">{{cite web|title=Rizatriptan|url=https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601109.html|website=MedlinePlus|publisher=U.S. National Library of Medicine|access-date=21 March 2018|archive-date=5 July 2016|archive-url=https://web.archive.org/web/20160705113031/https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601109.html|url-status=live}}</ref> A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.<ref name="rizavssuma">{{cite journal | vauthors = Göbel H | title = Efficacy and tolerability of rizatriptan 10 mg compared with sumatriptan 100 mg: an evidence-based analysis.| journal = Expert Rev Neurother | volume = 10 | issue = 4 | pages = 499–506| date = 2010 | pmid = 20367203| doi = 10.1586/ern.10.24| s2cid = 43395810}}</ref>

==Contraindications==
Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.<ref name="tenyears"/>

==Adverse effects==
Frequent adverse effects (incidence less than 10%) are dizziness, drowsiness, asthenia/fatigue, and nausea. Clinical adverse experiences were typically mild and short-lasting (2–3 hours).<ref name="tenyears">{{cite journal | vauthors = Hargreaves RJ, Lines CR, Rapoport AM, Ho TW, Sheftell FD | title = Ten years of rizatriptan: from development to clinical science and future directions.| journal = Headache | date = 2009 | volume = 49| pages = S3–S20| pmid = 19161563| doi = 10.1111/j.1526-4610.2008.01335.x| s2cid = 23587019}}</ref>

== Interactions==
* [[Propranolol]]<ref name="Millson 2000">{{cite journal | vauthors = Millson DS, Tepper SJ, Rapoport AM | title = Migraine pharmacotherapy with oral triptans: a rational approach to clinical management | journal = Expert Opinion on Pharmacotherapy | volume = 1 | issue = 3 | pages = 391–404 | date = March 2000 | pmid = 11249525 | doi = 10.1517/14656566.1.3.391 | s2cid = 36053513 }}</ref>{{Explain|date=October 2024}}

==Pharmacology==
===Mechanism of action===
{{Further|Serotonin receptor agonist|Triptan#Mechanism of action}}

Rizatriptan acts as an agonist at serotonin [[5-HT1B|5-HT<sub>1B</sub>]] and [[5-HT1D|5-HT<sub>1D</sub>]] receptors.<ref name="Wellington 2002">{{cite journal | vauthors = Wellington K, Plosker GL | title = Rizatriptan: an update of its use in the management of migraine | journal = Drugs | volume = 62 | issue = 10 | pages = 1539–74 | year = 2002 | pmid = 12093318 | doi = 10.2165/00003495-200262100-00007 | s2cid = 195693597 }}</ref> Like the other [[triptans]] [[sumatriptan]] and [[zolmitriptan]], rizatriptan induces [[vasoconstriction]]—possibly by inhibiting the release of [[calcitonin gene-related peptide]] from sensory neurons in the [[trigeminal nerve]].<ref name="Wellington 2002"/>

==Chemistry==
The experimental [[log P]] is 1.4 and its predicted log P is 1.67 to 1.77.<ref name="PubChem">{{cite web | title=Rizatriptan | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/5078 | access-date=27 June 2025}}</ref><ref name="DrugBank">{{cite web | title=Rizatriptan: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=14 June 2012 | url=https://go.drugbank.com/drugs/DB00953 | access-date=27 June 2025}}</ref>

== Society and culture ==
===Brand names===
Brand names include Rizalt, Rizalt RPD, Rizact (India), Rizafilm,<ref name="Rizafilm FDA label" /> Maxalt,<ref name="Maxalt FDA label" /> and Maxalt-MLT.<ref name="Maxalt FDA label" /><ref>{{Cite web |title=Rishum01_5_982075622.pdf |url=https://mohpublic.z6.web.core.windows.net/IsraelDrugs/Rishum01_5_982075622.pdf |access-date=December 21, 2023 |website=Mohpublic.z6.web.core.windows.net}}</ref><ref>{{Cite web |title=Maxalt Oral: Uses, Side Effects, Interactions, Pictures, Warnings & More |url=https://www.webmd.com/drugs/2/drug-8440/maxalt-oral/details |access-date=December 21, 2023 |website=WebMD |archive-date=21 December 2023 |archive-url=https://web.archive.org/web/20231221221212/https://www.webmd.com/drugs/2/drug-8440/maxalt-oral/details |url-status=live }}</ref><ref>{{Cite web |title=Rizact 10 mg Tablet - Uses, Dosage, Side Effects, Composition |url=https://www.practo.com/medicine-info/rizact-10-mg-tablet-36132 |access-date=December 21, 2023 |website=Practo |archive-date=21 December 2023 |archive-url=https://web.archive.org/web/20231221221212/https://www.practo.com/medicine-info/rizact-10-mg-tablet-36132 |url-status=live }}</ref>

== References ==
{{reflist}}

{{Triptans}}
{{Serotonergics}}
{{Tryptamines}}
{{Merck&Co}}
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{{Authority control}}

[[Category:5-HT1D agonists]]
[[Category:N,N-Dialkyltryptamines]]
[[Category:Drugs developed by Merck & Co.]]
[[Category:Headaches]]
[[Category:Triazoles]]
[[Category:Triptans]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Dimethylamino compounds]]