Rizatriptan

Rizatriptan

Rizatriptan
Systematic (IUPAC) name
N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
Clinical data
Trade names Maxalt
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
Legal status
  • (Prescription only)
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability 45%
Protein binding 14%
Metabolism by monoamine oxidase
Biological half-life 2–3 hours
Excretion 82% urine; 12% faeces
Identifiers
CAS Registry Number  Y
ATC code N02
PubChem CID:
IUPHAR/BPS
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  N
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C15H19N5
Molecular mass 269.345 g/mol
 N   

Rizatriptan (trade name Maxalt) is a 5-HT1 receptor agonist of the triptan class of drugs developed by Merck & Co. for the treatment of migraine headaches.[1] It is available in strengths of 5 and 10 mg as tablets and orally disintegrating tablets (Maxalt-MLT).

Maxalt obtained approval by the United States Food and Drug Administration (FDA) on June 29, 1998. It is a second-generation triptan.

Rizatriptan is available only by prescription in Australia, Finland, the United States, Canada and New Zealand. Similarly, it is classed as a POM (Prescription Only Medicine) in the United Kingdom, Italy (as Rizaliv), France, Israel (as Rizalt), The Netherlands, Croatia and Spain (as Maxalt).

Contents

  • Indications 1
  • Contraindications 2
  • Adverse effects 3
  • Mechanism of action 4
  • Synthesis 5
  • References 6
  • External links 7

Indications

Rizatriptan is FDA-approved to treat acute migraine attacks with or without aura. It does not prevent future migraine attacks.[1] Rizatriptan is also used off-label to treat cluster headaches.

Contraindications

Adverse effects

Mechanism of action

Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.[2] 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.[2]

Synthesis

Rizatriptan synthesis:[3]

References

  1. ^ a b "Rizatriptan". MedlinePlus. U.S. National Library of Medicine. 
  2. ^ a b Wellington, K; Plosker, G. L. (2002). "Rizatriptan: An update of its use in the management of migraine". Drugs 62 (10): 1539–74.  
  3. ^ Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J.; Cottrell, I. F.; Houghton, P. G. (1994). "Synthesis of the 5-HT1D receptor agonist MK-0462 via a Pd-catalyzed coupling reaction". Tetrahedron Letters 35 (38): 6981.  

External links