Chemistry:Rizatriptan

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Short description: Medication used for the treatment of migraine headaches
Rizatriptan
Rizatriptan Structural Formula V.1.svg
Rizatriptan 3D ball-and-stick.png
Clinical data
Trade namesMaxalt, Maxalt-MLT, Rizafilm, others
AHFS/Drugs.comMonograph
MedlinePlusa601109
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classTriptan
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability45%
Protein binding14%
MetabolismBy monoamine oxidase
Elimination half-life2–3 hours
Excretion82% urine; 12% feces
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC15H19N5
Molar mass269.352 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (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 2020, it was the 134th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[7][8]

Medical uses

Rizatriptan is indicated to treat acute migraine attacks with or without aura.[1][2] It does not prevent future migraine attacks.[9] A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.[10]

Contraindications

Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.[11]

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).[11]

Interactions

Mechanism of action

Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.[13] 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.[13]

Society and culture

Brand names

Brand names include Rizalt, Rizalt RPD, Rizact (India), Rizafilm,[2] Maxalt,[1] and Maxalt-MLT.[1][14][15][16]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Maxalt- rizatriptan benzoate tablet; Maxalt-MLT- rizatriptan benzoate tablet, orally disintegrating". 1 June 2022. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=007b4644-e0e7-4863-9ae3-fe09676b3f5f. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Archived copy". https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/205394s000lbl.pdf. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Rizatriptan Benzoate Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/rizatriptan-benzoate.html. 
  4. ↑ 4.0 4.1 British National Formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 473. ISBN 9780857113382. 
  5. ↑ "Drug Approval Package: Maxalt/Rizatritan Benzoate NDA# 20864 & 20865". 30 March 2001. https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20864-20865.cfm. 
  6. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 531. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531. 
  7. ↑ "The Top 300 of 2020". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  8. ↑ "Rizatriptan - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Rizatriptan. 
  9. ↑ "Rizatriptan". U.S. National Library of Medicine. https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601109.html. 
  10. ↑ "Efficacy and tolerability of rizatriptan 10 mg compared with sumatriptan 100 mg: an evidence-based analysis.". Expert Rev Neurother 10 (4): 499–506. 2010. doi:10.1586/ern.10.24. PMID 20367203. 
  11. ↑ 11.0 11.1 "Ten years of rizatriptan: from development to clinical science and future directions.". Headache 49: S3–S20. 2009. doi:10.1111/j.1526-4610.2008.01335.x. PMID 19161563. 
  12. ↑ "Migraine pharmacotherapy with oral triptans: a rational approach to clinical management". Expert Opinion on Pharmacotherapy 1 (3): 391–404. March 2000. doi:10.1517/14656566.1.3.391. PMID 11249525. 
  13. ↑ 13.0 13.1 "Rizatriptan: an update of its use in the management of migraine". Drugs 62 (10): 1539–74. 2002. doi:10.2165/00003495-200262100-00007. PMID 12093318. 
  14. ↑ "Rishum01_5_982075622.pdf". https://mohpublic.z6.web.core.windows.net/IsraelDrugs/Rishum01_5_982075622.pdf. 
  15. ↑ "Maxalt Oral: Uses, Side Effects, Interactions, Pictures, Warnings & More". https://www.webmd.com/drugs/2/drug-8440/maxalt-oral/details. 
  16. ↑ "Rizact 10 mg Tablet - Uses, Dosage, Side Effects, Composition". https://www.practo.com/medicine-info/rizact-10-mg-tablet-36132. 



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