Rizatriptan
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Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches.<ref name="Maxalt FDA label" /><ref name=AHFS2019/> It is taken by mouth.<ref name="Maxalt FDA label" /><ref name=AHFS2019>Template:Cite web</ref> It can also be applied on the tongue.<ref name="Rizafilm FDA label" /> It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).<ref name="Maxalt FDA label" /><ref name="Rizafilm FDA label" />
Common side effects include chest pain, dizziness, dry mouth, and tingling.<ref name=AHFS2019/> Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis.<ref name=AHFS2019/> Excessive use may result in medication overuse headaches.<ref name=AHFS2019/> Use is not recommended during pregnancy and breastfeeding is not recommended within 24 hours after taking a dose.<ref name=BNF76/> Rizatriptan is in the triptan class and is believed to work by activating the 5-HT1 receptor.<ref name=AHFS2019/>
Rizatriptan was patented in 1991 and came into medical use in 1998.<ref name="FDA2001">Template:Cite web</ref><ref name=Fis2006>Template:Cite book</ref> It is available as a generic medication.<ref name=BNF76>Template:Cite book</ref> In 2023, it was the 208th most commonly prescribed medication in the United States, with more than 2Template:Nbspmillion prescriptions.<ref>Template:Cite web</ref><ref>Template:Cite web</ref> Rizatriptan is available in combination with meloxicam as meloxicam/rizatriptan.
Medical uses
Rizatriptan is indicated to treat acute migraine attacks with or without aura.<ref name="Maxalt FDA label" /><ref name="Rizafilm FDA label" /> It does not prevent future migraine attacks.<ref name="MedlinePlus">Template:Cite web</ref> A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.<ref name="rizavssuma">Template:Cite journal</ref>
Contraindications
Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.<ref name="tenyears"/>
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).<ref name="tenyears">Template:Cite journal</ref>
Interactions
Rizatriptan has an important but complex interaction with a metabolite of the beta blocker propranolol.<ref name="MillsonTepperRapoport2000">Template:Cite journal</ref> This interaction involves the enzyme monoamine oxidase A (MAO-A).<ref name="MillsonTepperRapoport2000" /> Due to the interaction, the dose of rizatriptan should be reduced to 5Template:Nbspmg when it is combined with propranolol.<ref name="MillsonTepperRapoport2000" />
Pharmacology
Mechanism of action
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 48–500 (Ki) >10,000 (Template:Abbrlink) 40% (Template:Abbrlink) |
| 5-HT1B | 3–138 (Ki) 1.4–234 (Template:Abbr) 74–99% (Template:Abbr) |
| 5-HT1D | 1.5–138 (Ki) 1.6–16 (Template:Abbr) 83–105% (Template:Abbr) |
| 5-HT1E | 87–316 (Ki) 6.8–870 (Template:Abbr) 107% (Template:Abbr) |
| 5-HT1F | 138–5,370 (Ki) 4.2–2,540 (Template:Abbr) 93% (Template:Abbr) |
| 5-HT2A | >10,000 (Ki) >10,000 (Template:Abbr) |
| 5-HT2B | 257–3,090 (Ki) 3,240 (Template:Abbr) |
| 5-HT2C | >3,160 (Ki) Template:Abbr (Template:Abbr) |
| 5-HT3 | >3,160 (mouse) |
| 5-HT4 | >3,160 (guinea pig) |
| 5-HT5A | 5,500 (rat) |
| 5-HT6 | >3,160 |
| 5-HT7 | 1,860–>10,000 (Ki) >10,000 (Template:Abbr) |
| α1A–α1D | Template:Abbr |
| α2A–α2C | Template:Abbr |
| β1–β3 | Template:Abbr |
| D1–D5 | Template:Abbr |
| H1–H4 | Template:Abbr |
| M1–M5 | Template:Abbr |
| I1, I2 | Template:Abbr |
| σ1, σ2 | Template:Abbr |
| Template:Abbrlink | Template:Abbr |
| Template:Abbrlink | Template:Abbr |
| Template:Abbrlink | Template:Abbr |
| Template:Abbrlink | Template:Abbr |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="BindingDB">Template:Cite web</ref><ref name="DeVriesVillalónSaxena1999">Template:Cite journal</ref><ref name="Tfelt-HansenDeVriesSaxena2000">Template:Cite journal</ref><ref name="DeleuHanssens2000">Template:Cite journal</ref><ref name="SaxenaTfelt-Hansen2001">Template:Cite journal</ref><ref name="Brink1999">Template:Cite web</ref><ref name="Broek2002">Template:Cite web</ref> <ref name="PauwelsTardifPalmier1997">Template:Cite journal</ref><ref name="NelsonPhebusJohnson2010">Template:Cite journal</ref><ref name="Rubio-BeltránLabastida-RamírezHaanes2019">Template:Cite journal</ref><ref name="PerezHalazyPauwels1999">Template:Cite journal</ref><ref name="ReuterNeeb2012">Template:Cite journal</ref><ref name="MitsikostasWard2024">Template:Cite book</ref><ref name="Comer2002">Template:Cite journal</ref> | |
Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.<ref name="Wellington 2002">Template:Cite journal</ref> 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.<ref name="Wellington 2002"/>
Chemistry
Rizatriptan, also known as 5-(1H-1,2,4-triazol-1-ylmethyl)-N,N-dimethyltryptamine, is a tryptamine derivative and a 5-substituted derivative of the psychedelic drug dimethyltryptamine (DMT).<ref name="PubChem" />
The experimental log P of rizatriptan is 1.4 and its predicted log P is 1.67 to 1.77.<ref name="PubChem">Template:Cite web</ref><ref name="DrugBank">Template:Cite web</ref>
History
Rizatriptan was patented in 1991 and was introduced for medical use in 1998.<ref name="FDA2001" /><ref name="Fis2006" />
Society and culture
Brand names
Brand names include Rizalt, Rizalt RPD, Rizact (India), Rizafilm,<ref name="Rizafilm FDA label" /> Maxalt,<ref name="Maxalt FDA label" /> and Maxalt-MLT.<ref name="Maxalt FDA label" /><ref>Template:Cite web</ref><ref>Template:Cite web</ref><ref>Template:Cite web</ref>
References
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