Rizatriptan

Rizatriptan
Clinical data
Trade namesMaxalt, Maxalt-MLT, Rizafilm, others
Other namesL-705126; L705126; MK-0462; MK0462; MK-462; MK462; 5-(1H-1,2,4-Triazol-1-ylmethyl)-N,N-dimethyltryptamine; 5-(1H-1,2,4-Triazol-1-ylmethyl)-DMT
AHFS/Drugs.comMonograph
MedlinePlusa601109
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classSerotonin 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptor agonist; Antimigraine agent; Triptan
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability45%
Protein binding14%
MetabolismBy monoamine oxidase
Elimination half-life2–3 hours
Excretion82% urine; 12% feces
Identifiers
IUPAC name
  • N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.243.719
Chemical and physical data
FormulaC15H19N5
Molar mass269.352 g·mol−1
3D model (JSmol)
SMILES
  • n1cncn1Cc2cc3c(cc2)[nH]cc3CCN(C)C
InChI
  • InChI=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 Y
  • Key:ULFRLSNUDGIQQP-UHFFFAOYSA-N Y
  (verify)

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches.[1][3] It is taken by mouth.[1][3] It can also be applied on the tongue.[2] It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).[1][2]

Common side effects include chest pain, dizziness, dry mouth, and tingling.[3] Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis.[3] Excessive use may result in medication overuse headaches.[3] Use is not recommended during pregnancy and breastfeeding is not recommended within 24 hours after taking a dose.[4] Rizatriptan is in the triptan class and is believed to work by activating the 5-HT1 receptor.[3]

Rizatriptan was patented in 1991 and came into medical use in 1998.[5][6] It is available as a generic medication.[4] In 2022, it was the 190th most commonly prescribed medication in the United States, with more than two million prescriptions.[7][8] Rizatriptan is available in combination with meloxicam as meloxicam/rizatriptan.

  1. ^ a b c d "Maxalt- rizatriptan benzoate tablet; Maxalt-MLT- rizatriptan benzoate tablet, orally disintegrating". DailyMed. 1 June 2022. Archived from the original on 23 March 2023. Retrieved 25 December 2023.
  2. ^ a b c "Archived copy" (PDF). Archived from the original (PDF) on 2 August 2023. Retrieved 25 December 2023.{{cite web}}: CS1 maint: archived copy as title (link)
  3. ^ a b c d e f "Rizatriptan Benzoate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 23 October 2020. Retrieved 18 March 2019.
  4. ^ a b British National Formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 473. ISBN 9780857113382.
  5. ^ "Drug Approval Package: Maxalt/Rizatritan Benzoate NDA# 20864 & 20865". U.S. Food and Drug Administration (FDA). 30 March 2001. Archived from the original on 6 December 2022. Retrieved 25 December 2023.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.
  7. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ^ "Rizatriptan Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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