Frovatriptan

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Frovatriptan
Clinical data
Trade namesFrova
Other namesSB-209509; SB209509; EN-3266; EN3266; VML-251; VML251
AHFS/Drugs.comMonograph
MedlinePlusa604013
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Oral
Drug classSerotonin 5-HT1B, 5-HT1D, 5-HT1F, and 5-HT7 receptor agonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability20–30%
MetabolismLiver
Elimination half-life26–30 hours[1]
ExcretionKidney
Identifiers
  • (+)-(R)-3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC14H17N3O
Molar mass243.310 g·mol−1
3D model (JSmol)
  • CN[C@@H]3CCc2[nH]c1ccc(C(N)=O)cc1c2C3
  • 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 checkY
  • Key:XPSQPHWEGNHMSK-SECBINFHSA-N checkY
  (verify)

Frovatriptan, sold under the brand name Frova among others, is a triptan medication developed by Vernalis for the treatment of migraine headaches[2] and for short term prevention of menstrual migraine.[3][4] The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.[5]

Medical uses

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Frovatriptan is used in the treatment of migraine.

Available forms

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It is available as 2.5 mg tablets.

Contraindications

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Frovatriptan should not be given to patients with:

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

Side effects

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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

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Pharmacodynamics

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Further information: Serotonin receptor agonist and Triptan § Mechanism of action
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: [6][7][1][8][4][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.[citation needed] Frovatriptan inhibits excessive dilation of arteries that supply blood to the head.[citation needed] 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

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

Chemistry

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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

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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

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

See also

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References

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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).
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