Rizatriptan

Last updated

Rizatriptan
Rizatriptan Structural Formula V.1.svg
Rizatriptan 3D ball-and-stick.png
Clinical data
Trade names Maxalt, Maxalt-MLT, Rizafilm, others
AHFS/Drugs.com Monograph
MedlinePlus a601109
License data
Pregnancy
category
  • AU:B1
Routes of
administration
By mouth
Drug class Triptan
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 45%
Protein binding 14%
Metabolism By monoamine oxidase
Elimination half-life 2–3 hours
Excretion 82% urine; 12% feces
Identifiers
  • N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.243.719 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H19N5
Molar mass 269.352 g·mol−1
3D model (JSmol)
  • n1cncn1Cc2cc3c(cc2)[nH]cc3CCN(C)C
  • 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 Yes check.svgY
  • Key:ULFRLSNUDGIQQP-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches. [1] [3] It is taken by mouth. [1] [3] It can also be applied on the tongue. [2] It is a serotonin (5-HT) 1B/1D receptor agonist (triptan). [1] [2]

Contents

Common side effects include chest pain, dizziness, dry mouth, and tingling. [3] Other side effects may include myocardial infarction, stroke, high blood pressure, serotonin syndrome, and anaphylaxis. [3] Excessive use may result in medication overuse headaches. [3] 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. [3]

Rizatriptan was patented in 1991 and came into medical use in 1998. [5] [6] It is available as a generic medication. [4] In 2021, it was the 159th most commonly prescribed medication in the United States, with more than 3 million prescriptions. [7] [8]

Medical uses

Rizatriptan is indicated to treat acute migraine attacks with or without aura. [1] [2] 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

Mechanism of action

Rizatriptan acts as an agonist at serotonin 5-HT1B and 5-HT1D receptors. [13] 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. [13]

Society and culture

Brand names

Brand names include Rizalt, Rizalt RPD, Rizact (India), Rizafilm, [2] Maxalt, [1] and Maxalt-MLT. [1] [14] [15] [16]

Related Research Articles

<span class="mw-page-title-main">Sumatriptan</span> Medication used for migraines & cluster headaches

Sumatriptan, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches. It is taken orally, intranasally, or by subcutaneous injection. Therapeutic effects generally occur within three hours.

<span class="mw-page-title-main">Ergotamine</span> Chemical compound in the ergot family of alkaloids

Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor. It is used for acute migraines, sometimes with caffeine as the combination ergotamine/caffeine.

<span class="mw-page-title-main">Triptan</span> Class of pharmaceutical drugs

Triptans are a family of tryptamine-based drugs used as abortive medication in the treatment of migraines and cluster headaches. This drug class was first commercially introduced in the 1990s. While effective at treating individual headaches, they do not provide preventive treatment and are not considered a cure. They are not effective for the treatment of tension–type headache, except in persons who also experience migraines. Triptans do not relieve other kinds of pain.

<span class="mw-page-title-main">Zolmitriptan</span> Medication used in treatment of migraines

Zolmitriptan, sold under the brand name Zomig among others, is a triptan used in the acute treatment of migraine attacks with or without aura and cluster headaches. It is a selective serotonin receptor agonist of the 1B and 1D subtypes.

<span class="mw-page-title-main">Prochlorperazine</span> Medication for nausea, psychosis, and anxiety

Prochlorperazine, formerly sold under the brand name Compazine among others, is a medication used to treat nausea, migraines, schizophrenia, psychosis and anxiety. It is a less preferred medication for anxiety. It may be taken by mouth, rectally, injection into a vein, or injection into a muscle.

<span class="mw-page-title-main">Dihydroergotamine</span> An ergot alkaloid used to treat migraines

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan. Nausea is a common side effect.

Ergotamine/caffeine, sold under the brand name Cafergot among others, is a fixed-dose combination medication used for the treatment of migraine. It contains ergotamine, as the tartrate, an alpha adrenergic blocking agent; and caffeine, a cranial vasoconstrictor.

<span class="mw-page-title-main">Methylergometrine</span> Chemical compound

Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.

<span class="mw-page-title-main">Methysergide</span> Chemical compound

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to adverse effects. It is taken by mouth.

<span class="mw-page-title-main">Almotriptan</span> Chemical compound

Almotriptan is a triptan medication discovered and developed by Almirall for the treatment of heavy migraine headache.

<span class="mw-page-title-main">Eletriptan</span> Chemical compound

Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc.

<span class="mw-page-title-main">Cyproheptadine</span> Antihistamine medication

Cyproheptadine, sold under the brand name Periactin among others, is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Antimigraine drug</span> Medication intended to reduce the effects or intensity of migraine headache

Antimigraine drugs are medications intended to reduce the effects or intensity of migraine headache. They include drugs for the treatment of acute migraine symptoms as well as drugs for the prevention of migraine attacks.

<span class="mw-page-title-main">Naratriptan</span> Chemical compound

Naratriptan (trade names include Amerge) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It is a selective 5-HT1 receptor subtype agonist.

Sumatriptan/naproxen, sold under the brand name Treximet among others, is a fixed-dose combination medication used to treat migraines. It is taken by mouth. It contains sumatriptan, as the succinate, a serotonin 5-hydroxytryptamine (5-HT) 1b/1d receptor agonist (triptan); and naproxen as the sodium salt, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs).

Triptans are a family of tryptamine-based drugs used as abortive medication in the treatment of migraines and cluster headaches. They are selective 5-hydroxytryptamine/serotonin1B/1D (5-HT1B/1D) agonists. Migraine is a complex disease which affects about 15% of the population and can be highly disabling. Triptans have advantages over ergotamine and dihydroergotamine, such as selective pharmacology, well established safety record and evidence-based prescribing instructions. Triptans are therefore often preferred treatment in migraine.

<span class="mw-page-title-main">Lasmiditan</span> Chemical compound

Lasmiditan, sold under the brand name Reyvow, is a medication used for the acute treatment of migraine with or without aura in adults. It is not useful for prevention. It is taken by mouth.

Migraine may be treated either prophylactically (preventive) or abortively (rescue) for acute attacks. Migraine is an complex condition; there are various preventive treatments which disrupt different links in the chain of events that occur during a migraine attack. Rescue treatments also target and disrupt different processes occurring during migraine.

<span class="mw-page-title-main">Ditan</span> Drug class

Ditans are a class of abortive medication for the treatment of migraines. The first ditan, Eli Lilly's lasmiditan, was approved by the FDA in 2019.

References

  1. 1 2 3 4 5 6 7 "Maxalt- rizatriptan benzoate tablet; Maxalt-MLT- rizatriptan benzoate tablet, orally disintegrating". DailyMed. 1 June 2022. Archived from the original on 23 March 2023. Retrieved 25 December 2023.
  2. 1 2 3 4 5 "Archived copy" (PDF). Archived (PDF) from the original on 2 August 2023. Retrieved 25 December 2023.{{cite web}}: CS1 maint: archived copy as title (link)
  3. 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.
  4. 1 2 British National Formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 473. ISBN   9780857113382.
  5. "Drug Approval Package: Maxalt/Rizatritan Benzoate NDA# 20864 & 20865". U.S. Food and Drug Administration (FDA). 30 March 2001. Archived from the original on 6 December 2022. Retrieved 25 December 2023.
  6. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN   9783527607495.
  7. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  8. "Rizatriptan - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  9. "Rizatriptan". MedlinePlus. U.S. National Library of Medicine. Archived from the original on 5 July 2016. Retrieved 21 March 2018.
  10. 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. S2CID   43395810.
  11. 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. 49: S3–S20. doi:10.1111/j.1526-4610.2008.01335.x. PMID   19161563. S2CID   23587019.
  12. 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. S2CID   36053513.
  13. 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. S2CID   195693597.
  14. "Rishum01_5_982075622.pdf" (PDF). Mohpublic.z6.web.core.windows.net. Retrieved 21 December 2023.
  15. "Maxalt Oral: Uses, Side Effects, Interactions, Pictures, Warnings & More". WebMD. Archived from the original on 21 December 2023. Retrieved 21 December 2023.
  16. "Rizact 10 mg Tablet - Uses, Dosage, Side Effects, Composition". Practo. Archived from the original on 21 December 2023. Retrieved 21 December 2023.