Frovatriptan Succinate

Details

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

SHOW SMILES / InChI

Structure Search

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	C4H6O4
Molecular Weight	118.088
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	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021006s006s009s010lbl.pdf

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	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=5618948.PN.&OS=PN/5618948&RS=PN/5618948	Agonist 2752	62.0 nM [Ki]
Serotonin 1b (5-HT1b) receptor 45 Target ID: CHEMBL1898 Sources: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=5618948.PN.&OS=PN/5618948&RS=PN/5618948	Agonist 2752	10.3 nM [Ki]
Serotonin 1d (5-HT1d) receptor 53 Target ID: CHEMBL1983 Sources: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=5618948.PN.&OS=PN/5618948&RS=PN/5618948	Agonist 2752	4.4 nM [Ki]
Serotonin 1d (5-HT1d) receptor 53 Target ID: CHEMBL1983 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021006s006s009s010lbl.pdf	Agonist 2752
Serotonin 1b (5-HT1b) receptor 45 Target ID: CHEMBL1898 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021006s006s009s010lbl.pdf	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine with aura 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021006s006s009s010lbl.pdf	Primary		Approved 8583	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
Migraine without aura 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021006s006s009s010lbl.pdf	Primary		Approved 8583	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

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf			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: https://pubmed.ncbi.nlm.nih.gov/12028321	healthy, 21 - 37 Health Status: healthy Age Group: 21 - 37 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12028321	Sources: https://pubmed.ncbi.nlm.nih.gov/12028321
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12028321	healthy, 21 - 37 Health Status: healthy Age Group: 21 - 37 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12028321	Sources: https://pubmed.ncbi.nlm.nih.gov/12028321
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/12028323	unhealthy, 40.4 Health Status: unhealthy Age Group: 40.4 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12028323	Sources: https://pubmed.ncbi.nlm.nih.gov/12028323
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021006s019lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8/9 42 CYP2C19 2057 CYP2E1 1060	CYP1A2 1197	CYP1A2 832 CYP4A 14

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 29, 35	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP2C8/9 42	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 29, 35	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP4A 34	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 29, 35	no

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 35.0	no
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-006_Frova_biopharmr.pdf Page: 29.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2U95
Alsachim	4232	http://www.alsachim.com/product-C5550-glo.bal-view.html
AN PharmaTech	AN-5267
Angene	AGN-PC-0Q7KOZ
BLD Pharm	BD131596	http://www.bldpharm.com/products/158747-02-5.html
BOC Sciences	147009-08-3
BOC Sciences	158930-09-7
BOC Sciences	158930-17-7
Chem Scene	CS-0021309
Chemieliva Pharmaceutical Co., Ltd	PBCM1202367
ChemMol	44000939	http://www.chemmol.com/chemmol/44000939.html
ChemMol	49400089	http://www.chemmol.com/chemmol/49400089.html
ChemShuttle	159065
Compound Cloud	152943
Compound Cloud	77992
DC Chemicals	DC22890	http://www.dcchemicals.com/product_show-DC22890.html
eMolecules	225791104
eMolecules	300452900
eMolecules	45916583
eMolecules	48667526
eMolecules	76760210
eNovation Chemicals	D380881
Hangzhou APIChem Technology	AC-4258
Molnova	M12269
MolPort	MolPort-046-196-805
MuseChem	M105240	https://www.musechem.com/product/M105240.html
Norris Pharm	NSZB-A219176
NovoSeek	77992
Parchem	29025	http://www.parchem.com/chemical-supplier-distributor/Frovatriptan-019025.aspx
Selleck Chemicals	S5848
Sigma Aldrich	1286413
Sigma Aldrich	1286413\|USP
Sigma Aldrich	SML1291
Sigma Aldrich	SML1291\|SIGMA
Smolecule	S528497	http://www.smolecule.com/products/s528497
THE BioTek	bt-268779	https://www.thebiotek.com/product/inhibitors/bt-268779
THE BioTek	bt-406286	https://www.thebiotek.com/product/others/bt-406286
Toronto Research Chemicals	M198100
Wonderchem	WD05AWA
Wonderchem	WD05AWB
ZINC	ZINC000000018635	http://zinc15.docking.org/substances/ZINC000000018635

PubMed

Title	Date	PubMed
Acute treatment and prevention of menstrually related migraine headache: evidence-based review.	2008-04-22	18427072
Triptans in pregnancy.	2008-02	18223456
Evaluation of clinical effectiveness of the Frova single-use tracheal tube introducer.	2008-02	18211451
Frovatriptan review.	2007-12	18001261
Menstrually related migraine: breaking the cycle in your clinical practice.	2007-10	17977161
Frovatriptan vs. transdermal oestrogens or naproxen sodium for the prophylaxis of menstrual migraine.	2007-10	17955167
Efficacy of frovatriptan.	2007-09	17883538
Frovatriptan for the prevention of postdural puncture headache.	2007-07	17598763
Times to pain relief and pain freedom with rizatriptan 10 mg and other oral triptans.	2007-07	17537184
Efficacy of frovatriptan.	2007-06	17578554
Frova intubating catheter position can be determined with aspirating oesophageal detection device.	2007-06	17564685
Chiral separation of Frovatriptan isomers by HPLC using amylose based chiral stationary phase.	2007-02-01	16962393
Latest pain relief a combination of new and old.	2007-01	17198336
New pain management options: drugs.	2007-01	17198138
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007-01	17003167
Use of the sustained pain-free plus no adverse events endpoint in clinical trials of triptans in acute migraine.	2007	17190530
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.	2006-12-20	17183637
Tracheal intubation using a classic laryngeal mask airway, Frova introducer, and pediatric bronchoscope.	2006-12	17122292
Gateways to clinical trials.	2006-11	17200730
Tailoring management strategies for the patient with menstrual migraine: focus on prevention and treatment.	2006-10	17044843
Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine.	2006-09	18360605
Editorial foreword.	2006-09	18360597
Airway management during microlaryngoscopic surgery with a Frova airway intubation catheter.	2006-09	16980166
A validated chiral CE method for Frovatriptan, using cyclodextrin as chiral selector.	2006-06-16	16672183
Shearing of a Frova Intubating Introducer by a Bronchocath double lumen tube.	2006-02	16430585
Clinical review: percutaneous dilatational tracheostomy.	2006-02	16356203
[Clinical use of triptans in the management of migraine].	2006	16841523
Efficacy and tolerability of frovatriptan in acute migraine treatment: systematic review of randomized controlled trials.	2005-12	16336284
The use of multiattribute decision models in evaluating triptan treatment options in migraine.	2005-09	15761676
Advanced strategies of short-term prophylaxis in menstrual migraine: state of the art and prospects.	2005-05	15926009
[Tracheotomy and tracheostomy techniques].	2005-05	15827706
A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine.	2005-03-08	15753451
Gateways to clinical trials.	2005-03	15834466
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.	2005-01	15726452
Regulatory and functional interactions of plant growth regulators and plant glutathione S-transferases (GSTs).	2005	16492471
The use of triptans in the management of menstrual migraine.	2005	16268666
Frovatriptan-induced hypomania.	2005	16179674
Frovatriptan for the treatment of cluster headaches.	2004-12	15566418
Tracheostomy must be individualized!	2004-10	15469591
Pharmacokinetics of frovatriptan in adolescent migraineurs.	2004-10	15342617
[Meta-analysis of triptan treatment in migraine].	2004-09	15552863
Gateways to clinical trials.	2004-09	15538546
Randomized, placebo-controlled comparison of early use of frovatriptan in a migraine attack versus dosing after the headache has become moderate or severe.	2004-09	15383196
Evaluation of Frova, single-use intubation introducer, in a manikin. Comparison with Eschmann multiple-use introducer and Portex single-use introducer.	2004-08	15270974
A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine.	2004-07-27	15277618
Menstrual migraine: timing is everything.	2004-07-27	15277607
Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine.	2004-07	15311727
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.	2004-07	15185063
Gateways to clinical trials.	2004-06	15319815
Gateways to clinical trials.	2004-05	15319808

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:44 GMT 2025`
Record UNII	D28J6W18HY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Frovatriptan succinate monohydrate

Preferred Name

English

Frovatriptan Succinate

Official 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