Chemistry:Frovatriptan

Short description: Chemical compound

Frovatriptan

Clinical data
Trade names	Frova
Other names	6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide (6R)-6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide
AHFS/Drugs.com	Monograph
MedlinePlus	a604013
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N02CC07 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20–30%
Metabolism	Hepatic
Elimination half-life	26 hours
Excretion	Renal
Identifiers
IUPAC name (+)-(R)-3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole
CAS Number	158747-02-5 Y succinate: 158930-17-7 Y
PubChem CID	77992
IUPHAR/BPS	7191
DrugBank	DB00998 Y
ChemSpider	70378 Y
UNII	H82Q2D5WA7 succinate: D28J6W18HY Y
KEGG	D07997 N
ChEMBL	ChEMBL1279 Y
Chemical and physical data
Formula	C14H17N3O
Molar mass	243.310 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN[C@@H]3CCc2[nH]c1ccc(C(N)=O)cc1c2C3
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
NY (what is this?)  (verify)

Frovatriptan, sold under the brand 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.

Medical uses

Frovatriptan is used in the treatment of migraine.

Available forms

It is available as 2.5 mg tablets.

Contraindications

Frovatriptan should not be given to patients with:

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

Side effects

Rare, but serious 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.

Pharmacology

Pharmacodynamics

Frovatriptan is a serotonin 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. Frovatriptan inhibits excessive dilation of arteries that supply blood to the head.

Pharmacokinetics

Frovatriptan has a terminal elimination half-life of approximately 26 hours, making it the longest within its class.

Society and culture

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.

External links

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