U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of FROVATRIPTAN

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

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FROVA

Approved Use

FROVA 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 Date

2001
Primary
FROVA

Approved Use

FROVA 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 Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.44 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
50.7 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
29.3 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
FROVATRIPTAN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Cerebral hemorrhage
Subarachnoid hemorrhage
Stroke
Gastrointestinal ischemia
Peripheral vasoconstriction
Serotonin syndrome
Other AEs:
Myocardial ischemia
Myocardial infarction
Prinzmetal angina
Chest pain
Throat pain
Neck pain
Jaw pain
Chest tightness
Throat tightness
Pressure
Sources: Page: p.1
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
Raynaud's syndrome
Blood pressure high (grade 3)
Hypertensive crisis
Anaphylactic reaction (grade 4-5)
Anaphylactoid reaction (grade 4-5)
Angioedema (grade 4-5)
Sources: Page: p.3
AEs

AEs

AESignificanceDosePopulation
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

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

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
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
Name Type Language
FROVATRIPTAN
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
FROVATRIPTAN [HSDB]
Common Name English
FROVATRIPTAN [VANDF]
Common Name English
FROVATRIPTAN [MI]
Common Name English
FROVATRIPTAN [MART.]
Common Name English
frovatriptan [INN]
Common Name English
Frovatriptan [WHO-DD]
Common Name English
(R)-5,6,7,8-TETRAHYDRO-6-(METHYLAMINO)CARBAZOLE-3-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175763
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
WHO-ATC N02CC07
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
NDF-RT N0000175765
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
WHO-VATC QN02CC07
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
NDF-RT N0000175764
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
LIVERTOX 443
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
Code System Code Type Description
MERCK INDEX
m5571
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C65772
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
SMS_ID
100000080448
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
FDA UNII
H82Q2D5WA7
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
LACTMED
Frovatriptan
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
IUPHAR
7191
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
DAILYMED
H82Q2D5WA7
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
HSDB
7363
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
RXCUI
228783
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00998
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
EVMPD
SUB07817MIG
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
DRUG CENTRAL
1251
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL1279
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
WIKIPEDIA
FROVATRIPTAN
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
INN
7661
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
PUBCHEM
77992
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
CAS
158747-02-5
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID0023080
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY
MESH
C108128
Created by admin on Fri Dec 15 15:59:27 GMT 2023 , Edited by admin on Fri Dec 15 15:59:27 GMT 2023
PRIMARY