Rizatriptan
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Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches.[1][2] It is taken by mouth.[1][2] It can also be applied on the tongue.[3] It is a serotonin (5-HT) 1B/1D receptor agonist (triptan).[1][3]
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.[4] 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.[5][6] It is available as a generic medication.[4] In 2023, it was the 208th most commonly prescribed medication in the United States, with more than 2Script error: No such module "String".million prescriptions.[7][8] Rizatriptan is available in combination with meloxicam as meloxicam/rizatriptan.
Medical uses
Rizatriptan is indicated to treat acute migraine attacks with or without aura.[1][3] It does not prevent future migraine attacks.[9] A 2010 review found rizatriptan to be more efficacious and tolerable than sumatriptan.[10]
Contraindications
Rizatriptan and other triptans can cause vasoconstriction, they are contraindicated in people with cardiovascular conditions.[11]
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).[11]
Interactions
Rizatriptan has an important but complex interaction with a metabolite of the beta blocker propranolol.[12] This interaction involves the enzyme monoamine oxidase A (MAO-A).[12] Due to the interaction, the dose of rizatriptan should be reduced to 5Script error: No such module "String".mg when it is combined with propranolol.[12]
Pharmacology
Mechanism of action
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| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 48–500 (Ki) >10,000 (EC50) 40% (Emax) |
| 5-HT1B | 3–138 (Ki) 1.4–234 (EC50) 74–99% (Emax) |
| 5-HT1D | 1.5–138 (Ki) 1.6–16 (EC50) 83–105% (Emax) |
| 5-HT1E | 87–316 (Ki) 6.8–870 (EC50) 107% (Emax) |
| 5-HT1F | 138–5,370 (Ki) 4.2–2,540 (EC50) 93% (Emax) |
| 5-HT2A | >10,000 (Ki) >10,000 (EC50) |
| 5-HT2B | 257–3,090 (Ki) 3,240 (EC50) |
| 5-HT2C | >3,160 (Ki) ND (EC50) |
| 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 (EC50) |
| α1A–α1D | ND |
| α2A–α2C | ND |
| β1–β3 | ND |
| D1–D5 | ND |
| H1–H4 | ND |
| M1–M5 | ND |
| I1, I2 | ND |
| σ1, σ2 | ND |
| TAAR1 | ND |
| SERT | ND |
| NET | ND |
| DAT | ND |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [13][14][15][16][17][18][19] [20][21][22][23][24][25][26] | |
Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors.[27] 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.[27]
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).[28]
The experimental log P of rizatriptan is 1.4 and its predicted log P is 1.67 to 1.77.[28][29]
History
Rizatriptan was patented in 1991 and was introduced for medical use in 1998.[5][6]
Society and culture
Brand names
Brand names include Rizalt, Rizalt RPD, Rizact (India), Rizafilm,[3] Maxalt,[1] and Maxalt-MLT.[1][30][31][32]
References
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