Rizatriptan

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]

Rizatriptan

Clinical data
Trade names	Maxalt, Maxalt-MLT, Rizafilm, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601109
License data	US DailyMed: Rizatriptan
Pregnancy category	AU: B1
Routes of administration	By mouth
Drug class	Triptan
ATC code	N02CC04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) / S3 CA: ℞-only US: ℞-only[1][2] In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	45%
Protein binding	14%
Metabolism	By monoamine oxidase
Elimination half-life	2–3 hours
Excretion	82% urine; 12% feces
Identifiers
IUPAC name N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine
CAS Number	145202-66-0 Y
PubChem CID	5078
IUPHAR/BPS	51
DrugBank	DB00953 Y
ChemSpider	4900 Y
UNII	WR978S7QHH
KEGG	D00675 N
ChEBI	CHEBI:48273 Y
ChEMBL	ChEMBL905 Y
CompTox Dashboard (EPA)	DTXSID2023565
ECHA InfoCard	100.243.719
Chemical and physical data
Formula	C15H19N5
Molar mass	269.352 g·mol−1
3D model (JSmol)	Interactive image
SMILES n1cncn1Cc2cc3c(cc2)[nH]cc3CCN(C)C
InChI 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 Y Key:ULFRLSNUDGIQQP-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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 2022, it was the 190th most commonly prescribed medication in the United States, with more than two 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][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

• Propranolol^{[12][further explanation needed]}

Mechanism of action

Further information: Serotonin receptor agonist and Triptan § Mechanism of action

Rizatriptan acts as an agonist at serotonin 5-HT_1B and 5-HT_1D 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]}