Rizatriptan

Rizatriptan
Names
Trade namesMaxalt, others
IUPAC name
  • N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
Clinical data
Drug classTriptan
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • B1 (Au), C (U.S.)
Routes of
use
By mouth
Defined daily dose10 mg[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa601109
Legal
License data
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetics
Bioavailability45%
Protein binding14%
Metabolismby monoamine oxidase
Elimination half-life2–3 hours
Excretion82% urine; 12% faeces
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

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches.[2] It should be used as soon as the headache starts.[3] It is taken by mouth.[2]

Common side effects include chest pain, dizziness, dry mouth, and tingling.[2] Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis.[2] Excessive use may result in medication overuse headaches.[2] Use is not recommended during pregnancy and breastfeeding is not recommended within 24 hours after taking a dose.[3] Rizatriptan is in the triptan class and is believed to work by activating the 5-HT1 receptor.[2]

Rizatriptan was patented in 1991 and came into medical use in 1998.[4] It is available as a generic medication.[3] A dose in the United Kingdom costs the NHS about 3.10 £ as of 2019.[3] In the United States the wholesale cost of this amount is about US$0.73.[5] In 2017, it was the 204th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

Medical uses

Rizatriptan is used to treat acute migraine attacks with or without aura. It does not prevent future migraine attacks.[8] A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.[9]

Dosage

The defined daily dose is 10 mg by mouth.[1]

Side effects

Frequent side effects (incidence less than 10%) are dizziness, drowsiness, asthenia/fatigue, and nausea. Clinical adverse experiences were typically mild and short-lasting (2–3 hours).[10]

Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.[10]

Interactions

Mechanism of action

Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.[12] 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.[12]

Society and culture

It is typically by prescription except in Brazil.

Cost

A dose in the United Kingdom costs the NHS about 3.10 £ as of 2019.[3] In the United States the wholesale cost of this amount is about US$0.73.[5] In 2017, it was the 204th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

Names

Brandnames include Bizaliv, Rizalt, and Maxalt.

References

  1. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 20 October 2020. Retrieved 7 September 2020.
  2. 1 2 3 4 5 6 "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.
  3. 1 2 3 4 5 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 473. ISBN 9780857113382.
  4. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495. Archived from the original on 2019-03-06. Retrieved 2019-03-02.
  5. 1 2 "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 2019-03-06. Retrieved 3 March 2019.
  6. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 11 April 2020.
  7. 1 2 "Rizatriptan Benzoate - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 11 April 2020.
  8. "Rizatriptan". MedlinePlus. U.S. National Library of Medicine. Archived from the original on 2016-07-05. Retrieved 2018-03-21.
  9. 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.{{cite journal}}: CS1 maint: uses authors parameter (link)
  10. 1 2 Hargreaves RJ, Lines CR, Rapoport AM, Ho TW, Sheftell FD. (2009). "Ten years of rizatriptan: from development to clinical science and future directions". Headache. doi:10.1111/j.1526-4610.2008.01335.x. PMID 19161563.{{cite journal}}: CS1 maint: uses authors parameter (link)
  11. 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.
  12. 1 2 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.
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