rizatriptan

{{Short description|Medication used for the treatment of migraine headaches}}

{{Use dmy dates|date=December 2023}}

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| image = Rizatriptan Structural Formula V.1.svg

| alt =

| image2 = Rizatriptan 3D ball-and-stick.png

| alt2 =

| 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 = By mouth

| class = Triptan

| ATC_prefix = N02

| ATC_suffix = CC04

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| legal_AU = S4

| legal_AU_comment = / S3

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| legal_BR_comment =

| legal_CA = Rx-only

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| legal_DE_comment =

| legal_NZ =

| legal_NZ_comment =

| legal_UK =

| legal_UK_comment =

| legal_US = Rx-only

| legal_US_comment = {{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 }}{{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 }}

| legal_EU =

| legal_EU_comment =

| legal_UN =

| legal_UN_comment =

| legal_status = Rx-only

| bioavailability = 45%

| protein_bound = 14%

| metabolism = By monoamine oxidase

| elimination_half-life = 2–3 hours

| excretion = 82% urine; 12% feces

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 145202-66-0

| PubChem = 5078

| IUPHAR_ligand = 51

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00953

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| ChemSpiderID = 4900

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = WR978S7QHH

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| KEGG = D00675

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| ChEBI = 48273

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 905

| IUPAC_name = N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine

| C = 15

| H = 19

| N = 5

| smiles = n1cncn1Cc2cc3c(cc2)[nH]cc3CCN(C)C

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| 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

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Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches. It is taken by mouth.{{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 }} It can also be applied on the tongue. It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).

Common side effects include chest pain, dizziness, dry mouth, and tingling. Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis. Excessive use may result in medication overuse headaches. Use is not recommended during pregnancy and breastfeeding is not recommended within 24 hours after taking a dose. Rizatriptan is in the triptan class and is believed to work by activating the 5-HT₁ receptor.

Rizatriptan was patented in 1991 and came into medical use in 1998.{{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 }}{{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 }} It is available as a generic medication.{{cite book|title=British National Formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=473|edition=76}} In 2022, it was the 190th most commonly prescribed medication in the United States, with more than two million prescriptions.{{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 }}{{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 }} Rizatriptan is available in combination with meloxicam as meloxicam/rizatriptan.