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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17N3O.C4H6O4.H2O
Molecular Weight 379.4076
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FROVATRIPTAN SUCCINATE

SMILES

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

InChI

InChIKey=CUETXFMONOSVJA-KLQYNRQASA-N
InChI=1S/C14H17N3O.C4H6O4.H2O/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);1H2/t9-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.0051776E12
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

1.0051776E12
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.
2001
Acute treatment of migraine and the role of triptans.
2001 Mar
Comparative effects of frovatriptan and sumatriptan on coronary and internal carotid vascular haemodynamics in conscious dogs.
2001 Mar
Advances in pharmacological treatment of migraine.
2001 Oct
Triptans are all different.
2001 Sep
Spotlight on rizatriptan in migraine.
2002
Clinical efficacy of frovatriptan: placebo-controlled studies.
2002 Apr
New medications show promise for migraine sufferers.
2002 Oct
Frovatriptan Vernalis.
2002 Sep
Newer formulations of the triptans: advances in migraine management.
2003
Patent news.
2003 Dec
New drugs 2003, part I.
2003 Feb
Frovatriptan: a review.
2003 Jan
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
Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine.
2004 Jul
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine.
2004 Jul 27
Menstrual migraine: timing is everything.
2004 Jul 27
Cost considerations of acute migraine treatment.
2004 Mar
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
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
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.
2005 Jan
Gateways to clinical trials.
2005 Mar
The use of multiattribute decision models in evaluating triptan treatment options in migraine.
2005 Sep
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.
2006 Dec 20
Frovatriptan review.
2007 Dec
Latest pain relief a combination of new and old.
2007 Jan
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 Fri Dec 16 18:48:06 UTC 2022
Edited
by admin
on Fri Dec 16 18:48:06 UTC 2022
Record UNII
D28J6W18HY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FROVATRIPTAN SUCCINATE
MART.   ORANGE BOOK   USAN   USP-RS  
USAN  
Official Name English
FROVATRIPTAN SUCCINATE MONOHYDRATE
MI   WHO-DD  
Common Name English
SB 209509-AX
Code English
SB 209509 AX
Code English
FROVA
Code English
MIGUARD
Brand Name English
FROVELAN
Brand Name English
(+)-(R)-2,3,4,9-TETRAHYDRO-3-(METHYLAMINO)-1H-CARBAZOLE-6-CARBOXAMIDE BUTANEDIOATE (1:1), MONOHYDRATE
Systematic Name English
SB-209509-AX
Code English
FROVATRIPTAN SUCCINATE [USP-RS]
Common Name English
FROVATRIPTAN SUCCINATE MONOHYDRATE [MI]
Common Name English
FROVATRIPTAN SUCCINATE [MART.]
Common Name English
VML 251
Code English
(+)-(R)-5,6,7,8-TETRAHYDRO-6-(METHYLAMINO)CARBAZOLE-3-CARBOXAMIDE SUCCINATE (1:1), MONOHYDRATE
Systematic Name English
FROVATRIPTAN SUCCINATE [USAN]
Common Name English
SB-209509AX
Code English
MIGARD
Brand Name English
FROVATRIPTAN SUCCINATE HYDRATE
Common Name English
BUTANEDIOIC ACID, COMPD. WITH (R)-2,3,4,9-TETRAHYDRO-3-(METHYLAMINO)-1H-CARBAZOLE-6-CARBOXAMIDE (1:1), MONOHYDRATE
Systematic Name English
Frovatriptan succinate monohydrate [WHO-DD]
Common Name English
VML-251
Code English
FROVATRIPTAN SUCCINATE [ORANGE BOOK]
Common Name English
NSC-760422
Code English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
Code System Code Type Description
RS_ITEM_NUM
1286413
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
RXCUI
322249
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M5571
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY Merck Index
NCI_THESAURUS
C47544
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
ChEMBL
CHEMBL1279
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
USAN
KK-26
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
FDA UNII
D28J6W18HY
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
DRUG BANK
DBSALT001958
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
CAS
158930-17-7
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
WIKIPEDIA
Frovatriptan succinate
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
PUBCHEM
152943
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
DAILYMED
D28J6W18HY
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
EPA CompTox
DTXSID2049056
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
EVMPD
SUB22174
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
NSC
760422
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
EVMPD
SUB127149
Created by admin on Fri Dec 16 18:48:06 UTC 2022 , Edited by admin on Fri Dec 16 18:48:06 UTC 2022
PRIMARY
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