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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17N3O
Molecular Weight 243.3043
Optical Activity ( + )
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

Molecular Formula C14H17N3O
Molecular Weight 243.3043
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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:
healthy, 21 - 37
Health Status: healthy
Age Group: 21 - 37
Sex: M+F
Sources:
40 mg single, oral
Highest studied dose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
healthy, 21 - 37
Health Status: healthy
Age Group: 21 - 37
Sex: M+F
Sources:
40 mg single, oral
Highest studied dose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
unhealthy, 40.4
Health Status: unhealthy
Age Group: 40.4
Sex: M+F
Sources:
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:
unhealthy
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:
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:
unhealthy
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:
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparative aspects of triptans in treating migraine.
2001
Newer formulations of the triptans: advances in migraine management.
2003
Migraine headache recurrence: relationship to clinical, pharmacological, and pharmacokinetic properties of triptans.
2003 Apr
Patent news.
2003 Dec
[Migraine therapy. new specific triptan frovatriptan--long acting].
2003 Jan
Meta-analysis of oral triptan therapy for migraine: number needed to treat and relative cost to achieve relief within 2 hours.
2003 Jan-Feb
The evolving management of migraine.
2003 Jun
Gateways to clinical trials.
2003 Jun
The truth about frovatriptan.
2003 Jun
Gateways to clinical trials.
2003 Oct
[After the numerous ergotamine preparations are on the way out. Migraine patients to change over to triptans].
2003 Oct 16
Gateways to clinical trials.
2004 Apr
Evaluation of Frova, single-use intubation introducer, in a manikin. Comparison with Eschmann multiple-use introducer and Portex single-use introducer.
2004 Aug
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Cost considerations of acute migraine treatment.
2004 Mar
Gateways to clinical trials.
2004 May
Frovatriptan use in migraineurs with or at high risk of coronary artery disease.
2004 May
[PercuTwist dilational tracheostomy. Prospective evaluation of 54 consecutive patients].
2004 May
Gateways to clinical trials.
2004 Sep
Regulatory and functional interactions of plant growth regulators and plant glutathione S-transferases (GSTs).
2005
The use of triptans in the management of menstrual migraine.
2005
Efficacy and tolerability of frovatriptan in acute migraine treatment: systematic review of randomized controlled trials.
2005 Dec
Frovatriptan-induced hypomania.
2005 Summer
[Clinical use of triptans in the management of migraine].
2006
Tracheal intubation using a classic laryngeal mask airway, Frova introducer, and pediatric bronchoscope.
2006 Dec
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.
2006 Dec 20
Shearing of a Frova Intubating Introducer by a Bronchocath double lumen tube.
2006 Feb
Clinical review: percutaneous dilatational tracheostomy.
2006 Feb
A validated chiral CE method for Frovatriptan, using cyclodextrin as chiral selector.
2006 Jun 16
Gateways to clinical trials.
2006 Nov
Tailoring management strategies for the patient with menstrual migraine: focus on prevention and treatment.
2006 Oct
Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine.
2006 Sep
Editorial foreword.
2006 Sep
Airway management during microlaryngoscopic surgery with a Frova airway intubation catheter.
2006 Sep
Use of the sustained pain-free plus no adverse events endpoint in clinical trials of triptans in acute migraine.
2007
Frovatriptan review.
2007 Dec
Chiral separation of Frovatriptan isomers by HPLC using amylose based chiral stationary phase.
2007 Feb 1
Latest pain relief a combination of new and old.
2007 Jan
New pain management options: drugs.
2007 Jan
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Frovatriptan for the prevention of postdural puncture headache.
2007 Jul
Times to pain relief and pain freedom with rizatriptan 10 mg and other oral triptans.
2007 Jul
Efficacy of frovatriptan.
2007 Jun
Frova intubating catheter position can be determined with aspirating oesophageal detection device.
2007 Jun
Menstrually related migraine: breaking the cycle in your clinical practice.
2007 Oct
Frovatriptan vs. transdermal oestrogens or naproxen sodium for the prophylaxis of menstrual migraine.
2007 Oct
Efficacy of frovatriptan.
2007 Sep
Acute treatment and prevention of menstrually related migraine headache: evidence-based review.
2008 Apr 22
Triptans in pregnancy.
2008 Feb
Evaluation of clinical effectiveness of the Frova single-use tracheal tube introducer.
2008 Feb
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:15:34 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:34 GMT 2025
Record UNII
H82Q2D5WA7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Frovatriptan
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
(R)-Frovatriptan
Preferred 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 Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
WHO-ATC N02CC07
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
NDF-RT N0000175765
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
WHO-VATC QN02CC07
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
NCI_THESAURUS C47794
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
NDF-RT N0000175764
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
LIVERTOX 443
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
Code System Code Type Description
MERCK INDEX
m5571
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C65772
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
SMS_ID
100000080448
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
FDA UNII
H82Q2D5WA7
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
LACTMED
Frovatriptan
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
IUPHAR
7191
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
DAILYMED
H82Q2D5WA7
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
HSDB
7363
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
RXCUI
228783
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00998
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
EVMPD
SUB07817MIG
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
DRUG CENTRAL
1251
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
ChEMBL
CHEMBL1279
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
WIKIPEDIA
FROVATRIPTAN
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
INN
7661
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
PUBCHEM
77992
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
CAS
158747-02-5
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID0023080
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
MESH
C108128
Created by admin on Mon Mar 31 18:15:34 GMT 2025 , Edited by admin on Mon Mar 31 18:15:34 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
pKi
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
oral administration
AMOUNT EXCRETED
FECAL
METABOLIC ENZYME -> SUBSTRATE
MAJOR
EXCRETED UNCHANGED
oral administration
AMOUNT EXCRETED
URINE
EXCRETED UNCHANGED
intravenous administration
AMOUNT EXCRETED
URINE
RACEMATE -> ENANTIOMER
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
FECAL
METABOLITE -> PARENT
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC