Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H17N3O |
Molecular Weight | 243.3043 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)C(N)=O
InChI
InChIKey=XPSQPHWEGNHMSK-SECBINFHSA-N
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
Frovatriptan succinate (trade name Frova) is a selective 5-hydroxytryptamine1 (5-HT1B/1D) receptor subtype agonist, and is used for the treatment of migraine attacks with or without aura in adults. 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. Serious but rare cardiac events have been reported in patients with risk factors predictive of coronary artery disease (CAD). These include coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia and ventricular fibrillation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
62.0 nM [Ki] | |||
10.3 nM [Ki] | |||
4.4 nM [Ki] | |||
Target ID: CHEMBL1983 |
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Target ID: CHEMBL1898 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date2001 |
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Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.44 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85% |
FROVATRIPTAN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 mg single, intravenous Highest studied dose Dose: 0.8 mg Route: intravenous Route: single Dose: 0.8 mg Sources: Page: S56 |
healthy, 21 - 37 n = 12 Health Status: healthy Age Group: 21 - 37 Sex: M+F Population Size: 12 Sources: Page: S56 |
|
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: S56 |
healthy, 21 - 37 n = 12 Health Status: healthy Age Group: 21 - 37 Sex: M+F Population Size: 12 Sources: Page: S56 |
|
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: S76 |
unhealthy, 40.4 n = 207 Health Status: unhealthy Condition: Migraine Age Group: 40.4 Sex: M+F Population Size: 207 Sources: Page: S76 |
|
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Disc. AE: Arrhythmia, Cerebral hemorrhage... Other AEs: Myocardial ischemia, Myocardial infarction... AEs leading to discontinuation/dose reduction: Arrhythmia Other AEs:Cerebral hemorrhage Subarachnoid hemorrhage Stroke Gastrointestinal ischemia Peripheral vasoconstriction Serotonin syndrome Myocardial ischemia Sources: Page: p.1Myocardial infarction Prinzmetal angina Chest pain Throat pain Neck pain Jaw pain Chest tightness Throat tightness Pressure |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Disc. AE: Splenic infarction, Raynaud's syndrome... AEs leading to discontinuation/dose reduction: Splenic infarction Sources: Page: p.3Raynaud's syndrome Blood pressure high (grade 3) Hypertensive crisis Anaphylactic reaction (grade 4-5) Anaphylactoid reaction (grade 4-5) Angioedema (grade 4-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chest pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Chest tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Jaw pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Myocardial infarction | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Myocardial ischemia | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Neck pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Pressure | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Prinzmetal angina | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Throat pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Throat tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Arrhythmia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Cerebral hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Gastrointestinal ischemia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Peripheral vasoconstriction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Serotonin syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Stroke | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Subarachnoid hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Hypertensive crisis | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Raynaud's syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Splenic infarction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Blood pressure high | grade 3 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Anaphylactic reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Anaphylactoid reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Angioedema | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Frovatriptan: pharmacological differences and clinical results. | 2001 |
|
Rizatriptan: an update of its use in the management of migraine. | 2002 |
|
Tolerability and safety of frovatriptan with short- and long-term use for treatment of migraine and in comparison with sumatriptan. | 2002 Apr |
|
Clinical efficacy of frovatriptan: placebo-controlled studies. | 2002 Apr |
|
Dose range-finding studies with frovatriptan in the acute treatment of migraine. | 2002 Apr |
|
[Migraine has many faces. Success in differential diagnosis]. | 2002 Aug 8 |
|
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials. | 2002 Oct |
|
Newer formulations of the triptans: advances in migraine management. | 2003 |
|
New drugs 2003, part I. | 2003 Feb |
|
[Also keeps long migraine attacks in check. A new triptan]. | 2003 Feb 6 |
|
[Migraine therapy. new specific triptan frovatriptan--long acting]. | 2003 Jan |
|
Frovatriptan: a review. | 2003 Jan |
|
The evolving management of migraine. | 2003 Jun |
|
Gateways to clinical trials. | 2003 Jun |
|
Gateways to clinical trials. | 2004 Jun |
|
Frovatriptan use in migraineurs with or at high risk of coronary artery disease. | 2004 May |
|
Tracheostomy must be individualized! | 2004 Oct |
|
Pharmacokinetics of frovatriptan in adolescent migraineurs. | 2004 Oct |
|
Randomized, placebo-controlled comparison of early use of frovatriptan in a migraine attack versus dosing after the headache has become moderate or severe. | 2004 Sep |
|
Gateways to clinical trials. | 2005 Mar |
|
Advanced strategies of short-term prophylaxis in menstrual migraine: state of the art and prospects. | 2005 May |
|
Frovatriptan-induced hypomania. | 2005 Summer |
|
Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. | 2006 Sep |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Efficacy of frovatriptan. | 2007 Jun |
|
Frova intubating catheter position can be determined with aspirating oesophageal detection device. | 2007 Jun |
|
Efficacy of frovatriptan. | 2007 Sep |
|
Acute treatment and prevention of menstrually related migraine headache: evidence-based review. | 2008 Apr 22 |
Sample Use Guides
The recommended dose is a single tablet of FROVA (frovatriptan 2.5 mg) taken orally with fluids. If the headache recurs after initial relief, a second tablet may be taken, providing there is an interval of at least 2 hours between doses. The total daily dose of frovatriptan should not exceed 3 tablets (3 x 2.5 mg per day). The safety of treating an average of more than 4 migraine attacks in a 30-day period has not been established.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9700983
Curator's Comment: Frovatriptan was investigated in human isolated basilar and coronary arteries in which the endothelium had been removed. Basilar arteries were obtained post mortem, and coronary arteries were obtained from patients undergoing heart transplant (recipient) or from donor hearts that were not suitable for transplant. Frovatriptan was a potent contractile agent in isolated basilar artery with a -log mean effective concentration (EC50) value of 7.86 +/- 0.07 and intrinsic activity of 1.25 +/- 0.10 relative to 5-HT (n = 4). In coronary arteries, frovatriptan produced contraction with -log EC50 values of 7.38 +/- 0.12 and 7.81 +/- 0.2 in recipient (n = 7) and donor (n = 3) arteries, respectively. The relative degree of contraction of frovatriptan was lower than that of 5-HT, with relative intrinsic activities of 0.42 +/- 0.06 and 0.40 +/- 0.09, respectively.
Unknown
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175763
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WHO-ATC |
N02CC07
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NDF-RT |
N0000175765
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WHO-VATC |
QN02CC07
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NCI_THESAURUS |
C47794
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NDF-RT |
N0000175764
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LIVERTOX |
443
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m5571
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C65772
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100000080448
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H82Q2D5WA7
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Frovatriptan
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DB00998
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C108128
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)