Frovatriptan

Identification

Summary

Frovatriptan is a 5-HT1B/1D receptor agonist used to treat migraines.

Brand Names
Frova
Generic Name
Frovatriptan
DrugBank Accession Number
DB00998
Background

Frovatriptan is a triptan drug developed by Vernalis for the treatment of migraine headaches, in particular those associated with menstruation. Frovatriptan causes vasoconstriction of arteries and veins that supply blood to the head.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 243.3043
Monoisotopic: 243.137162181
Chemical Formula
C14H17N3O
Synonyms
  • Frovatriptan
External IDs
  • SB 209509

Pharmacology

Indication

For the acute treatment of migraine attacks with or without aura in adults.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofMenstrual migraine••• •••••
Treatment ofMigraine with aura•••••••••••••••••••••••
Treatment ofMigraine without aura•••••••••••••••••••••••
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Pharmacodynamics

Frovatriptan is a second generation triptan 5-HT receptor agonist that binds with high affinity for 5-HT1B and 5-HT1D receptors. It is structurally distinct from, but pharmacologically related to other selective 5-HT1B/1D receptor agonists. Frovatriptan has no significant effects on GABAA mediated channel activity and has no significant affinity for benzodiazepine binding sites. Frovatriptan is believed to act on extracerebral, intracranial arteries and to inhibit excessive dilation of these vessels in migraine. Research has shown that migraine can be caused by the swelling of blood vessels around the brain. Frovatriptan eases the pain associated with migraine by narrowing these blood vessels. Frovatriptan has one of the highest affinities for the 5-HT1B of the second-generation triptan agonists.

Mechanism of action

Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1D
agonist
Humans
A5-hydroxytryptamine receptor 1B
agonist
Humans
Absorption

Frovatriptan is rapidly absorbed from the duodenum, but has low oral bioavailability.

Volume of distribution
  • 4.2 L/kg [males]
  • 3 L/kg [females]
Protein binding

Binding to serum proteins is low (approximately 15%). Reversible binding to blood cells at equilibrium is approximately 60%.

Metabolism

In vitro, cytochrome P450 1A2 appears to be the principal enzyme involved in the metabolism of frovatriptan to several metabolites including hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, and several other minor metabolites. Desmethyl frovatriptan has lower affinity for 5-HT1B/1D receptors compared to the parent compound. The N-acetyl desmethyl metabolite has no significant affinity for 5-HT receptors. The activity of the other metabolites is unknown.

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Route of elimination

Radiolabeled compounds excreted in urine were unchanged frovatriptan, hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, together with several other minor metabolites. Less than 10% of frovatriptan was excreted in urine after an oral dose.

Half-life

26 hours

Clearance
  • 220 mL/min [male receiving IV dose of 0.8 mg]
  • 130 mL/min [Female receiving IV dose of 0.8 mg]
Adverse Effects
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Toxicity

There is no direct experience of any patient taking an overdose of Frovatriptan. The maximum single dose of frovatriptan given to male and female patients with migraine was 40 mg (16 times the clinical dose) and the maximum single dose given to healthy male subjects was 100 mg (40 times the clinical dose) without significant adverse events.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to frovatriptan when treating (condition: cluster headache).Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Frovatriptan is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Frovatriptan can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Frovatriptan can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Frovatriptan can be increased when it is combined with Abiraterone.
AcebutololFrovatriptan may decrease the antihypertensive activities of Acebutolol.
Food Interactions
  • Take with or without food. Food does not affect bioavailability, but delays maximum concentrations by one hour.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Frovatriptan succinateD28J6W18HY158930-17-7CUETXFMONOSVJA-KLQYNRQASA-N
Frovatriptan succinate anhydrous36K05YF32G158930-09-7WHTHWNUUXINXHN-SBSPUUFOSA-N
Product Images
International/Other Brands
Frova / Miguard
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FrovaTablet, film coated2.5 mg/1OralUnit Dose Services2001-11-082017-12-31US flag
FrovaTablet, film coated2.5 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-08-182017-06-01US flag
FrovaTablet, film coated2.5 mg/1OralStat Rx USA2001-11-08Not applicableUS flag
FrovaTablet2.5 mgOralEndo Pharmaceuticals2008-01-04Not applicableCanada flag
FrovaTablet, film coated2.5 mg/1OralEndo Pharmaceuticals, Inc.2001-11-08Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-frovatriptanTablet2.5 mgOralApotex Corporation2014-08-11Not applicableCanada flag
FrovatriptanTablet, film coated2.5 mg/1OralIngenus Pharmaceuticals, LLC2022-07-22Not applicableUS flag
FrovatriptanTablet, film coated2.5 mg/1OralMylan Pharmaceuticals Inc.2016-04-292023-04-30US flag
FrovatriptanTablet, film coated2.5 mg/1OralAmneal Pharmaceuticals NY LLC2018-11-13Not applicableUS flag
Frovatriptan SuccinateTablet, film coated2.5 mg/1OralGlenmark Pharmaceuticals Inc., USA2016-03-11Not applicableUS flag

Categories

ATC Codes
N02CC07 — Frovatriptan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Carbazoles
Direct Parent
Carbazoles
Alternative Parents
Indolecarboxamides and derivatives / 3-alkylindoles / Aralkylamines / Benzenoids / Pyrroles / Heteroaromatic compounds / Primary carboxylic acid amides / Amino acids and derivatives / Dialkylamines / Azacyclic compounds
show 4 more
Substituents
3-alkylindole / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbazole / Carboxamide group / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
H82Q2D5WA7
CAS number
158747-02-5
InChI Key
XPSQPHWEGNHMSK-SECBINFHSA-N
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
IUPAC Name
(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide
SMILES
CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O

References

Synthesis Reference

Samir Naik, Anthony Crasto, Narendra Joshi, Sachin Srivastava, "Amorphous frovatriptan succinate and process for the preparation thereof." U.S. Patent US20070299123, issued December 27, 2007.

US20070299123
General References
  1. Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [Article]
  2. Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [Article]
  3. Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [Article]
  4. Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [Article]
  5. Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [Article]
  6. Jhee SS, Shiovitz T, Crawford AW, Cutler NR: Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review. Clin Pharmacokinet. 2001;40(3):189-205. [Article]
Human Metabolome Database
HMDB0015133
KEGG Drug
D07997
PubChem Compound
77992
PubChem Substance
46506288
ChemSpider
70378
BindingDB
50073689
RxNav
228783
ChEBI
134991
ChEMBL
CHEMBL1279
ZINC
ZINC000000018635
Therapeutic Targets Database
DAP000063
PharmGKB
PA164754891
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Frovatriptan
FDA label
Download (871 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionMigraine1
4CompletedTreatmentMenstrual Migraine (MM) Headaches1
3CompletedNot AvailableMigraine1
3CompletedPreventionMenstrually Associated Migraine1
3CompletedTreatmentMigraine2

Pharmacoeconomics

Manufacturers
  • Endo pharmaceuticals inc
Packagers
  • DispenseXpress Inc.
  • Elan Pharmaceuticals Inc.
  • Endo Pharmaceuticals Inc.
  • Pharmaceutical Development and Manufacturing Services Ltd.
  • Stat Rx Usa
  • Warner Chilcott Co. Inc.
Dosage Forms
FormRouteStrength
TabletOral2.5 mg
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral
TabletOral
Tablet, film coatedOral2.5 MG
Prices
Unit descriptionCostUnit
Frova 9 2.5 mg tablet Box262.31USD box
Frova 2.5 mg tablet33.73USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5962501No1999-10-052013-12-16US flag
CA2113726No2008-02-192012-06-17Canada flag
CA2152630No2005-07-262013-12-16Canada flag
US5464864No1995-11-072015-11-07US flag
US5827871No1998-10-272015-10-27US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.123 mg/mLALOGPS
logP1.2ALOGPS
logP1.08Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)14.54Chemaxon
pKa (Strongest Basic)10.42Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area70.91 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity71.84 m3·mol-1Chemaxon
Polarizability27.63 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier+0.986
Caco-2 permeable-0.5794
P-glycoprotein substrateSubstrate0.602
P-glycoprotein inhibitor INon-inhibitor0.8862
P-glycoprotein inhibitor IINon-inhibitor0.7244
Renal organic cation transporterNon-inhibitor0.6147
CYP450 2C9 substrateNon-substrate0.7785
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.6997
CYP450 2C9 inhibitorNon-inhibitor0.8842
CYP450 2D6 inhibitorNon-inhibitor0.8614
CYP450 2C19 inhibitorNon-inhibitor0.6656
CYP450 3A4 inhibitorNon-inhibitor0.5316
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5744
Ames testNon AMES toxic0.7623
CarcinogenicityNon-carcinogens0.9456
BiodegradationNot ready biodegradable0.9406
Rat acute toxicity1.9582 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9878
hERG inhibition (predictor II)Inhibitor0.6428
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-3690000000-20d2133e95fbc6b1f414
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-0090000000-22692ba065a6b315c9cd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0090000000-210f69a36d2eac8a9969
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0290000000-bdc6cd115757ee576770
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-c86eb1a80ee9fe73c149
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1910000000-4c03aff9c8c6e4123a0a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01vk-0940000000-a8cc7402b35923ab13cb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-168.4135289
predicted
DarkChem Lite v0.1.0
[M-H]-168.2481289
predicted
DarkChem Lite v0.1.0
[M-H]-155.1603
predicted
DeepCCS 1.0 (2019)
[M+H]+169.4572289
predicted
DarkChem Lite v0.1.0
[M+H]+169.2161289
predicted
DarkChem Lite v0.1.0
[M+H]+157.5183
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.4824289
predicted
DarkChem Lite v0.1.0
[M+Na]+168.3196289
predicted
DarkChem Lite v0.1.0
[M+Na]+163.9811
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
Learn more
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [Article]
  3. Comer MB: Pharmacology of the selective 5-HT(1B/1D) agonist frovatriptan. Headache. 2002 Apr;42 Suppl 2:S47-53. [Article]
  4. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [Article]
  5. Deleu D, Hanssens Y: Current and emerging second-generation triptans in acute migraine therapy: a comparative review. J Clin Pharmacol. 2000 Jul;40(7):687-700. [Article]
  6. Jahnichen S, Radtke OA, Pertz HH: Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):54-63. Epub 2004 Jun 8. [Article]
  7. Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [Article]
  8. Parsons AA, Raval P, Smith S, Tilford N, King FD, Kaumann AJ, Hunter J: Effects of the novel high-affinity 5-HT(1B/1D)-receptor ligand frovatriptan in human isolated basilar and coronary arteries. J Cardiovasc Pharmacol. 1998 Aug;32(2):220-4. [Article]
  9. Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [Article]
  10. Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [Article]
  11. Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [Article]
  3. Comer MB: Pharmacology of the selective 5-HT(1B/1D) agonist frovatriptan. Headache. 2002 Apr;42 Suppl 2:S47-53. [Article]
  4. Parsons AA, Raval P, Smith S, Tilford N, King FD, Kaumann AJ, Hunter J: Effects of the novel high-affinity 5-HT(1B/1D)-receptor ligand frovatriptan in human isolated basilar and coronary arteries. J Cardiovasc Pharmacol. 1998 Aug;32(2):220-4. [Article]
  5. Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [Article]
  6. Dodick DW, Sandrini G, Williams P: Use of the sustained pain-free plus no adverse events endpoint in clinical trials of triptans in acute migraine. CNS Drugs. 2007;21(1):73-82. [Article]
  7. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [Article]
  8. Deleu D, Hanssens Y: Current and emerging second-generation triptans in acute migraine therapy: a comparative review. J Clin Pharmacol. 2000 Jul;40(7):687-700. [Article]
  9. Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [Article]
  10. Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [Article]
  11. Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [Article]
  12. Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [Article]
  2. Buchan P, Keywood C, Wade A, Ward C: Clinical pharmacokinetics of frovatriptan. Headache. 2002 Apr;42 Suppl 2:S54-62. [Article]
  3. Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [Article]
  4. Fovatriptan FDA label [File]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48