frovatriptan
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461114004
| IUPAC_name = (+)-(R)-3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole
| image = Frovatriptan structure.svg
| image2 = Frovatriptan 3D BS.png
| tradename = Frova
| Drugs.com = {{drugs.com|monograph|frova}}
| MedlinePlus = a604013
| pregnancy_US = C
| pregnancy_AU = B3
| legal_status = Prescription only
| routes_of_administration = Oral
| bioavailability = 20–30%
| metabolism = Hepatic
| elimination_half-life = 26 hours
| excretion = Renal
| IUPHAR_ligand = 7191
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 158747-02-5
| ATC_prefix = N02
| ATC_suffix = CC07
| PubChem = 77992
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00998
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 70378
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H82Q2D5WA7
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D07997
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1279
| index2_label = succinate
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 158930-17-7
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = D28J6W18HY
| synonyms = 6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide
(6R)-6-methylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide
| C=14 | H=17 | N=3 | O=1
| SMILES = CN[C@@H]3CCc2[nH]c1ccc(C(N)=O)cc1c2C3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XPSQPHWEGNHMSK-SECBINFHSA-N
}}
Frovatriptan, sold under the brand name Frova, is a triptan drug developed by Vernalis for the treatment of migraine headaches{{cite journal | vauthors = Allais G, Benedetto C | title = Spotlight on frovatriptan: a review of its efficacy in the treatment of migraine | journal = Drug Design, Development and Therapy | volume = 10 | issue = | pages = 3225–3236 | date = 2016 | pmid = 27757013 | pmc = 5055118 | doi = 10.2147/DDDT.S105932 | url = | doi-access = free }} and for short term prevention of menstrual migraine.{{cite journal | vauthors = MacGregor EA | title = A review of frovatriptan for the treatment of menstrual migraine | journal = International Journal of Women's Health | volume = 6 | issue = | pages = 523–35 | date = 2014 | pmid = 24904224 | pmc = 4039425 | doi = 10.2147/IJWH.S63444 | doi-access = free }} The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.{{cite web|title=Frova |url=http://www.vernalis.com/ver/rdc2/pain/frovatriptan/ |publisher=Vernalis |access-date=2007-11-28 |archive-url=https://web.archive.org/web/20070927225521/http://www.vernalis.com/ver/rdc2/pain/frovatriptan/ |archive-date=2007-09-27 |url-status=dead }}
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=
{{Further|Serotonin receptor agonist|Triptan#Mechanism_of_action}}
Frovatriptan is a serotonin receptor agonist, with high affinity for the 5-HT1B/1D receptors. It has no significant effects on the GABAA 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.{{Cite journal|last=Balbisi|first=Ebrahim|date=September 2006|title=Frovatriptan: A Review of Pharmacology, Pharmacokinetics and Clinical Potential in the Treatment of Menstrual Migraine|journal=Therapeutics and Clinical Risk Management|volume=2|issue=3|pages=303–308|doi=10.2147/tcrm.2006.2.3.303|pmid=18360605|pmc=1936266 |doi-access=free }}
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.{{cite web|title=Patient Information Sheet -- Frovatriptan succinate (marketed as Frova) |url=https://www.fda.gov/cder/drug/InfoSheets/patient/frovatripanPIS.htm |date=July 2006 |publisher=Food and Drug Administration |access-date=2007-11-28 |archive-url=https://web.archive.org/web/20070929141557/https://www.fda.gov/cder/drug/InfoSheets/patient/frovatripanPIS.htm |archive-date=2007-09-29 |url-status=dead }}
References
{{Reflist}}
External links
- [http://www.frova.com/ Frova] (manufacturer's website)
- [http://www.healthcentral.com/migraine/r/medications/frova-oral-22253/uses Frovatriptan Succinate] (patient information)
- [https://web.archive.org/web/20090413231807/http://129.128.185.122/drugbank2/drugs/DB00998/fda_labels/907 FDA labeling]
{{Antimigraine preparations}}
{{Serotonin receptor modulators}}
{{Tryptamines}}