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 | monograph |
| MedlinePlus | a601109 |
| Pregnancy cat. | |
| Legal status |
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| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 45% |
| Protein binding | 14% |
| Metabolism | by monoamine oxidase |
| Half-life | 2–3 hours |
| Excretion | 82% urine; 12% faeces |
| Identifiers | |
| CAS number | 145202-66-0 |
| ATC code | N02CC04 |
| PubChem | CID 5078 |
| IUPHAR ligand | 51 |
| DrugBank | DB00953 |
| ChemSpider | 4900 |
| UNII | WR978S7QHH |
| KEGG | D00675 |
| ChEBI | CHEBI:48273 |
| ChEMBL | CHEMBL905 |
| Chemical data | |
| Formula | C15H19N5 |
| Mol. mass | 269.345 g/mol |
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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), Israel (as Rizalt), The Netherlands, Croatia and Spain (as Maxalt).
Contents
Indications[edit]
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[edit]
Adverse effects[edit]
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Severe:
Atypical sensations: Ear, nose, and throat: |
Muscular: Neurological: Respiratory: Skin: Miscellaneous: |
Mechanism of action[edit]
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[edit]
References[edit]
- ^ a b "Rizatriptan". MedlinePlus. U.S. National Library of Medicine.
- ^ a b Wellington, K; Plosker, G. L. (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.
- ^ 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. doi:10.1016/0040-4039(94)88204-5.
External links[edit]
- Maxalt website by Merck & Co.
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