Rizatriptan

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 category	B1 (Au), C (U.S.)
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	45%
Protein binding	14%
Metabolism	by monoamine oxidase
Biological half-life	2–3 hours
Excretion	82% urine; 12% faeces
Identifiers
CAS Number	145202-66-0 Y
ATC code	N02CC04 (WHO)
PubChem	CID: 5078
IUPHAR/BPS	51
DrugBank	DB00953 Y
ChemSpider	4900 Y
UNII	WR978S7QHH Y
KEGG	D00675 N
ChEBI	CHEBI:48273 Y
ChEMBL	CHEMBL905 Y
Chemical data
Formula	C15H19N5
Molecular mass	269.345 g/mol
SMILES n1cn(nc1)Cc2cc3c(cc2)ncc3CCN(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)

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. 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), France, Israel (as Rizalt), The Netherlands, Croatia and Spain (as Maxalt).

Indications

Rizatriptan is FDA-approved to treat acute migraine attacks with or without aura. It does not prevent future migraine attacks. Rizatriptan is also used off-label to treat cluster headaches.

Contraindications

• coronary artery disease
• use of monoamine oxidase inhibitors

Adverse effects

Severe:

• serotonin syndrome when used with MAOIs
• coronary artery vasospasm
• transient myocardial ischemia           
• myocardial infarction
• ventricular tachycardia
• ventricular fibrillation
• hypertensive crisis

Atypical sensations:

• paresthesia

Cardiovascular:

• palpitations
• syncope
• hypertension
• hypotension

Ear, nose, and throat:

• tinnitus
• sinusitis
• allergic rhinitis
• upper respiratory tract inflammation

Gastrointestinal:

• diarrhea

Muscular:

• myalgia

Neurological:

• phonophobia
• photophobia

Respiratory:

• dyspnea

Skin:

• sweating

Miscellaneous:

• hypersensitivity

Mechanism of action

Main article: Serotonin receptor agonist

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

External links

• Maxalt website by Merck & Co.