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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17N3O.C4H6O4
Molecular Weight 361.3923
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FROVATRIPTAN SUCCINATE ANHYDROUS

SMILES

OC(=O)CCC(O)=O.CN[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)C(N)=O

InChI

InChIKey=WHTHWNUUXINXHN-SBSPUUFOSA-N
InChI=1S/C14H17N3O.C4H6O4/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13;5-3(6)1-2-4(7)8/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18);1-2H2,(H,5,6)(H,7,8)/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

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Comparative aspects of triptans in treating migraine.
2001
Spotlight on rizatriptan in 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
Clinical pharmacokinetics of frovatriptan.
2002 Apr
[Treatment of migraine in patients with hypertension and ischemic heart disease].
2002 Jan 20
Gateways to Clinical Trials. June 2002.
2002 Jun
Gateways to clinical trials.
2002 Nov
Newer formulations of the triptans: advances in migraine management.
2003
Pharmacological approaches to migraine.
2003
[Migraine therapy. new specific triptan frovatriptan--long acting].
2003 Jan
Frovatriptan: a review.
2003 Jan
The truth about frovatriptan.
2003 Jun
Gateways to clinical trials.
2004 Apr
Tracheostomy must be individualized!
2004 Oct
The use of triptans in the management of menstrual migraine.
2005
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.
2005 Jan
A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine.
2005 Mar 8
[Tracheotomy and tracheostomy techniques].
2005 May
Tracheal intubation using a classic laryngeal mask airway, Frova introducer, and pediatric bronchoscope.
2006 Dec
A validated chiral CE method for Frovatriptan, using cyclodextrin as chiral selector.
2006 Jun 16
Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine.
2006 Sep
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
Frovatriptan vs. transdermal oestrogens or naproxen sodium for the prophylaxis of menstrual migraine.
2007 Oct
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 Sat Dec 16 05:59:32 GMT 2023
Edited
by admin
on Sat Dec 16 05:59:32 GMT 2023
Record UNII
36K05YF32G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FROVATRIPTAN SUCCINATE ANHYDROUS
MI  
Common Name English
FROVATRIPTAN SUCCINATE ANHYDROUS [MI]
Common Name English
BUTANEDIOIC ACID, COMPD. WITH (3R)-2,3,4,9-TETRAHYDRO-3-(METHYLAMINO)-1H-CARBAZOLE-6-CARBOXAMIDE (1:1)
Common Name English
(+)-(R)-2,3,4,9-TETRAHYDRO-3-(METHYLAMINO)-1H-CARBAZOLE-6-CARBOXAMIDE BUTANEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000088414
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
CAS
158930-09-7
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
DRUG BANK
DBSALT001957
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
PUBCHEM
152944
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
MERCK INDEX
m5571
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID90166543
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
FDA UNII
36K05YF32G
Created by admin on Sat Dec 16 05:59:32 GMT 2023 , Edited by admin on Sat Dec 16 05:59:32 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS