Frovatriptan

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| _other_data=(+)-(R)-3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole

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Frovatriptan, sold under the brand name Frova among others, is a triptan medication developed by Vernalis for the treatment of migraine headaches[1] and for short term prevention of menstrual migraine.[2][3] The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.[4]

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

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Frovatriptan activities
Target Affinity (Ki, nM)
5-HT1A 50–62 (Ki)
759–>10,000 (EC50Tooltip half-maximal effective concentration)
38% (EmaxTooltip maximal efficacy)
5-HT1B 2.5–46 (Ki)
6.3–20 (EC50)
92% (Emax)
5-HT1D 1.7–10 (Ki)
2–5 (EC50)
98% (Emax)
5-HT1E >1,000 (Ki)
6,610–>10,000 (EC50)
44% (Emax)
5-HT1F 63–120 (Ki)
79–447 (EC50)
46% (Emax)
5-HT2A >10,000 (Ki)
>10,000 (EC50)
5-HT2B >10,000 (Ki)
>10,000 (EC50)
5-HT2C >5,000 (Ki)
ND (EC50)
5-HT3 >1,000 (mouse/rat)
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 107–200 (Ki)
38 (EC50)
α1 >10,000 (rat)
α1A–α1D ND
α2A–α2C ND
β1–β3 ND
D1 >10,000
D2 >10,000
D3 >10,000
D4–D5 ND
H1 >10,000 (guinea pig)
H2–H4 ND
M1–M5 ND
I1, I2 ND
σ1, σ2 ND
TAAR1Tooltip Trace amine-associated receptor 1 ND
SERTTooltip Serotonin transporter ND
NETTooltip Norepinephrine transporter ND
DATTooltip Dopamine transporter ND
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [5][6][7][8][3][9][10]
[11][12][13][14][15]

Frovatriptan is a serotonin receptor agonist, with high affinity for the serotonin 5-HT1B and 5-HT1D receptors and with weaker activity at the serotonin 5-HT1F receptor.[12] It has no significant effects on the GABAA mediated channel activity and benzodiazepine binding sites.Script error: No such module "Unsubst". Frovatriptan inhibits excessive dilation of arteries that supply blood to the head.Script error: No such module "Unsubst". Uniquely among most triptans, frovatriptan is also a relatively potent serotonin 5-HT7 receptor agonist.[12] It is inactive at the serotonin 5-HT2A and 5-HT2B receptors.[12]

Pharmacokinetics

Frovatriptan has a terminal elimination half-life of approximately 26 hours, making it the longest within its class.[16]

Chemistry

Frovatriptan's chemical structure is unusual among triptans, with other triptans being simple tryptamines or closely related compounds but frovatriptan instead being a tricyclic cyclized tryptamine and tetrahydrocarbazolamine derivative.[17] It can be thought of as a 5-substituted and side chain-cyclized derivative of N-methyltryptamine (NMT).[17]

The experimental log P of frovatriptan is 0.9 and its predicted log P is 1.2.[18]

History

Frovatriptan was first described in the scientific literature by 1997.[19][20][21] It was approved for medical use in the United States in 2001.[22]

Society and culture

Legal status

Frovatriptan is available only by prescription in the United States and Canada.[23]

See also

References

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  1. ↑ Script error: No such module "Citation/CS1".
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  19. ↑ Brown, A. M., Parsons, A. A., Raval, P., Porter, R., Tilford, N. S., Gager, T. L., ... & King, F. D. (1996, October). SB 209509 (VML 251), a potent constrictor of rabbit basilar artery with high affinity and selectivity for human 5-HT1D receptors. In BRITISH JOURNAL OF PHARMACOLOGY (Vol. 119, pp. P110-P110).
  20. ↑ Script error: No such module "Citation/CS1".
  21. ↑ Script error: No such module "Citation/CS1".
  22. ↑ Script error: No such module "citation/CS1".
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