FROVATRIPTAN

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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 172	Agonist 2,678	62.0 nM [Ki]
Serotonin 1b (5-HT1b) receptor 46	Agonist 2,678	10.3 nM [Ki]
Serotonin 1d (5-HT1d) receptor 52	Agonist 2,678	4.4 nM [Ki]
Serotonin 1d (5-HT1d) receptor 52	Agonist 2,678
Serotonin 1b (5-HT1b) receptor 46	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine with aura 11	Primary		Approved 8,429	FROVA
Migraine without aura 7	Primary		Approved 8,429	FROVA

C_max

Value	Dose	Co-administered	Analyte	Population
2.44 ng/mL	2.5 mg single, oral		FROVATRIPTAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
50.7 ng × h/mL	2.5 mg single, oral		FROVATRIPTAN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
29.3 h	2.5 mg single, oral		FROVATRIPTAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
85%			FROVATRIPTAN serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
0.8 mg single, intravenous Highest studied dose	healthy, 21 - 37
40 mg single, oral Highest studied dose	healthy, 21 - 37
40 mg single, oral Highest studied dose	unhealthy, 40.4
7.5 mg 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Arrhythmia, Cerebral hemorrhage... Other AEs: Myocardial ischemia, Myocardial infarction...
7.5 mg 3 times / day multiple, oral Recommended	unhealthy	Disc. AE: Splenic infarction, Raynaud's syndrome...

Showing 1 to 5 of 5 entries

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AEs

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AE	Dose	Population
Chest pain	7.5 mg 3 times / day multiple, oral Recommended	unhealthy
Chest tightness	7.5 mg 3 times / day multiple, oral Recommended	unhealthy
Jaw pain	7.5 mg 3 times / day multiple, oral Recommended	unhealthy
Myocardial infarction	7.5 mg 3 times / day multiple, oral Recommended	unhealthy
Myocardial ischemia	7.5 mg 3 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 inducer 781 substrate 1,737	substrate 1,037	inhibitor 1,852 substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C8/9 44 CYP2C19 1,478 CYP2E1 882	CYP1A2 1,054	CYP1A2 701 CYP4A 14

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	no
CYP2C8/9 44	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	no

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Drug as victim

Show entries

Target	Modality	Activity
CYP2C9 1,037	substrate 3,367	no
CYP2D6 1,217	substrate 3,367	no
CYP3A4 1,737	substrate 3,367	no
CYP1A2 1,054	substrate 3,367	yes

Showing 1 to 4 of 4 entries

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Sourcing

Sourcing

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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

Showing 1 to 5 of 41 entries

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PubMed

Show entries

Title	Date	PubMed
Frovatriptan.	2001	11735616
Oral triptans (serotonin 5-HT(1B/1D) agonists) in acute migraine treatment: a meta-analysis of 53 trials.	2001 Nov 17	11728541
Frovatriptan: a review of drug-drug interactions.	2002 Apr	12028322
Clinical pharmacokinetics of frovatriptan.	2002 Apr	12028321
[Treatment of migraine in patients with hypertension and ischemic heart disease].	2002 Jan 20	12122940

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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