Frovatriptan

Frovatriptan

Systematic (IUPAC) name
(+)-(R)-3-methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole
Clinical data
Trade names	Frova
AHFS/Drugs.com	monograph
MedlinePlus	a604013
Pregnancy cat.	B3 (AU) C (US)
Legal status	Prescription only
Routes	Oral
Pharmacokinetic data
Bioavailability	20–30%
Metabolism	Hepatic
Half-life	26 hours
Excretion	Renal
Identifiers
CAS number	158930-17-7 N
ATC code	N02CC07
PubChem	CID 77992
DrugBank	DB00998
ChemSpider	70378 Y
UNII	H82Q2D5WA7 Y
KEGG	D07997 N
ChEMBL	CHEMBL1279 Y
Synonyms	6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide (6R)-6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide
Chemical data
Formula	C14H17N3O
Mol. mass	243.304 g/mol
SMILES O=C(N)c3ccc1c(c2c(n1)CC[C@@H](NC)C2)c3
InChI InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1 Y Key:XPSQPHWEGNHMSK-SECBINFHSA-N Y
N (what is this?)  (verify)

Frovatriptan (trade name Frova) is a triptan drug developed by Vernalis for the treatment of migraine headaches and for short term prevention of menstrual migraine. The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.

Pharmacology

Frovatriptan inhibits excessive dilation of arteries that supply blood to the head. It is available as 2.5 mg tablets.

Frovatriptan has mean terminal elimination half-life of approximately 26 hours, which is substantially longer than other triptans.

Mechanism of action

Frovatriptan is a 5HT receptor agonist, with high affinity for the 5-HT_1B/1D receptors. It has no significant effects on the GABA_A mediated channel activity and benzodiazepine binding sites.

Adverse effects

Serious but rare cardiac events have been reported in patients with risk factors predictive of CAD. These include: coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia and ventricular fibrillation.

Contraindications

Frovatriptan should not be given to patients with:

• Ischemic heart disease
• Cerebrovascular syndrome
• Peripheral vascular disease
• Uncontrolled hypertension
• Hemiplegic or basilar migraine

US licensing

Frovatriptan is available only by prescription in the United States, and Canada where a secondary New Drug Approval (sNDA) was filed in July 2006, and which is currently pending. The FDA anticipates completing its review of this application on or before the current PDUFA (Prescription Drug User Fee Act) review date of August 19, 2007. If the sNDA is approved, Frova will be the only medication indicated in the U.S. for the short-term prevention of menstrual migraine (MM).

External links

• Frova (manufacturer's website)
• Frovatriptan Succinate (patient information)
• FDA labeling