Rizatriptan

From Wikipedia, the free encyclopedia
Rizatriptan
Rizatriptan Structural Formula V.1.svg
Rizatriptan 3D ball-and-stick.png
Clinical data
Trade namesMaxalt, others
AHFS/Drugs.comMonograph
MedlinePlusa601109
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classTriptan
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S3
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability45%
Protein binding14%
MetabolismBy monoamine oxidase
Elimination half-life2–3 hours
Excretion82% urine; 12% faeces
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 Edit this at Wikidata
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 checkY
  • Key:ULFRLSNUDGIQQP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches.[1] It is taken by mouth.[1]

Common side effects include chest pain, dizziness, dry mouth, and tingling.[1] Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis.[1] Excessive use may result in medication overuse headaches.[1] Use is not recommended during pregnancy and breastfeeding is not recommended within 24 hours after taking a dose.[2] Rizatriptan is in the triptan class and is believed to work by activating the 5-HT1 receptor.[1]

Rizatriptan was patented in 1991 and came into medical use in 1998.[3] It is available as a generic medication.[2] In 2019, it was the 162nd most commonly prescribed medication in the United States, with more than 3 million prescriptions.[4][5]

Medical uses[]

Rizatriptan is used to treat acute migraine attacks with or without aura. It does not prevent future migraine attacks.[6] A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.[7]

Contraindications[]

Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.[8]

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).[8]

Interactions[]

Mechanism of action[]

Further information: Serotonin receptor agonist and Triptan § Mechanism_of_action

Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.[10] 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.[10]

Names[]

Brand names include Bizaliv, Rizalt, Rizact (India) and Maxalt.

References[]

  1. ^ a b c d e f "Rizatriptan Benzoate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 18 March 2019.
  2. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 473. ISBN 9780857113382.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.
  4. ^ "The Top 300 of 2019". ClinCalc. Retrieved 16 October 2021.
  5. ^ "Rizatriptan - Drug Usage Statistics". ClinCalc. Retrieved 16 October 2021.
  6. ^ "Rizatriptan". MedlinePlus. U.S. National Library of Medicine.
  7. ^ Göbel H (2010). "Efficacy and tolerability of rizatriptan 10 mg compared with sumatriptan 100 mg: an evidence-based analysis". Expert Rev Neurother. 10 (4): 499–506. doi:10.1586/ern.10.24. PMID 20367203. S2CID 43395810.CS1 maint: uses authors parameter (link)
  8. ^ a b Hargreaves RJ, Lines CR, Rapoport AM, Ho TW, Sheftell FD. (2009). "Ten years of rizatriptan: from development to clinical science and future directions". Headache. 49: S3–S20. doi:10.1111/j.1526-4610.2008.01335.x. PMID 19161563. S2CID 23587019.CS1 maint: uses authors parameter (link)
  9. ^ Millson DS, Tepper SJ, Rapoport AM (March 2000). "Migraine pharmacotherapy with oral triptans: a rational approach to clinical management". Expert Opinion on Pharmacotherapy. 1 (3): 391–404. doi:10.1517/14656566.1.3.391. PMID 11249525. S2CID 36053513.
  10. ^ a b Wellington K, Plosker GL (2002). "Rizatriptan: an update of its use in the management of migraine". Drugs. 62 (10): 1539–74. doi:10.2165/00003495-200262100-00007. PMID 12093318.

External links[]

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