Frovatriptan (CED0010031)

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:08 UTC

Update Date

2026-05-14 16:55:21 UTC

SynCED ID

CED0010031

Secondary Accession Numbers

CHEM002317
T3D2954

Identification

Common Name

Frovatriptan

Class

Small Molecule

Description

Frovatriptan is an exogenous organic compound with the formula C14H17N3O and an average molecular weight of 243.30 g/mol. It exists as a solid at room temperature. Frovatriptan belongs to the carbazoles, a subclass of indoles and derivatives within the organic compounds. This compound is recorded as being found in or released from five sources, including analgesics within healthcare, pharmaceuticals and veterinary products, household cleaning and consumer products such as other smoking requisites and non electric simulated smoking devices, and electrical and electronic equipment including television systems and electric hearing aids. The recorded exposure route is oral. Frovatriptan targets the 5-hydroxytryptamine receptor 1B (HTR1B) and 5-hydroxytryptamine receptor 1D (HTR1D). Three distinct pharmacological actions are implicated in the antimigraine effect of triptans: the stimulation of presynaptic 5-HT1D receptors, which inhibits dural inflammation and vasodilation; direct inhibition of trigeminal nuclei cell excitability through 5-HT1B/1D receptor agonism in the brainstem; and vasoconstriction of pial, cerebral, dural, or meningeal vessels resulting from vascular 5-HT1B receptor agonism.

Contaminant Type

Amide
Amine
Anti-Inflammatory Agent
Anti-Migraine Agent
Drug
Ester
Metabolite
Organic Compound
Serotonin Agonist
Serotonin Receptor Agonist
Synthetic Compound
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Allergo filmtabletten	Kegg
Frovatriptan succinate	HMDB
3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole	HMDB
Frovelan	HMDB
VML-251	HMDB
Allegro	HMDB
Frova	HMDB
(+)-(R)-5,6,7,8-Tetrahydro-6-(methylamino)carbazole-3-carboxamide succinate (1:1), monohydrate	HMDB

Chemical Formula

C₁₄H₁₇N₃O

Average Molecular Mass

243.304 g/mol

Monoisotopic Mass

243.137 g/mol

CAS Registry Number

158747-02-5

IUPAC Name

(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide

Traditional Name

frovatriptan

SMILES

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

InChI Identifier

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

InChI Key

XPSQPHWEGNHMSK-SECBINFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indolecarboxamide derivative
Indolecarboxylic acid derivative
3-alkylindole
Indole
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.54	ChemAxon
pKa (Strongest Basic)	10.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.84 m³·mol⁻¹	ChemAxon
Polarizability	27.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-3690000000-20d2133e95fbc6b1f414	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0190000000-fc527e672048d9bf866c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0490000000-09182e67659519af87e7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0l1i-0910000000-81f4aa818323e96b5464	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-bd79ad698f8bd9fbb84b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2490000000-4632cbf11a6dc353d2cf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9200000000-948170ac23122892a5ad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-168fda82142bf345541b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-0090000000-3dac4efa84856ab16486	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0910000000-bdfabb283d321aa1d9e3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-932ee60351365d51e611	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1190000000-c3fd5753f8f9a8a098eb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-4910000000-8fac1192455fd2253b72	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
254.0 Log mg/kg [140:450]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT_1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT_1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT_1B receptor agonism.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

There is no direct experience of any patient taking an overdose of Frovatriptan. The maximum single dose of frovatriptan given to male and female patients with migraine was 40 mg (16 times the clinical dose) and the maximum single dose given to healthy male subjects was 100 mg (40 times the clinical dose) without significant adverse events.

Treatment

As with other 5-HT1 receptor agonists, there is no specific antidote for frovatriptan. The elimination half-life of frovatriptan is 26 hours, therefore if overdose occurs, the patient should be monitored closely for at least 48 hours and be given any necessary symptomatic treatment. (8)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000370	Analgesics?Analgesics are a class of synthetic chemicals designed to alleviate pain.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000516	Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000592	Marine Propulsion Or Steering?Marine propulsion and steering systems often rely on various synthetic chemicals, including lubricants, fuels, and hydraulic fluids.	Marine, shipping & aquaculture	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000651	Purses Money Bags Wallets?Purses, money bags, and wallets are often manufactured using synthetic materials, including plastics, polyurethanes, and various treated fabrics.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Frovatriptan Mechanism of Action Action Pathway

Frovatriptan Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.471 Applicability Domain 0.857 Statistical Significance 0.0085 Supporting Reference Compounds 953 E-value 66.2497
Click to view 3D structure	5-hydroxytryptamine receptor 1E	P28566	Humans	Predicted (SEA)	Prediction Confidence Score 0.469 Applicability Domain 0.857 Statistical Significance 2.60e-04 Supporting Reference Compounds 139 E-value 2.02408
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.453 Applicability Domain 0.857 Statistical Significance 0.0057 Supporting Reference Compounds 565 E-value 44.5298
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	Prediction Confidence Score 0.444 Applicability Domain 0.857 Statistical Significance 0.0028 Supporting Reference Compounds 337 E-value 21.8756
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.412 Applicability Domain 0.857 Statistical Significance 0.0188 Supporting Reference Compounds 1103 E-value 146.357
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.406 Applicability Domain 0.46 Statistical Significance 0.0041 Supporting Reference Compounds 365 E-value 31.9182
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 0.394 Statistical Significance 0.0154 Supporting Reference Compounds 541 E-value 120.121
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.372 Applicability Domain 0.857 Statistical Significance 0.0289 Supporting Reference Compounds 527 E-value 225.374
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	Prediction Confidence Score 0.367 Applicability Domain 0.857 Statistical Significance 0.0077 Supporting Reference Compounds 298 E-value 60.0996
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	Prediction Confidence Score 0.367 Applicability Domain 0.857 Statistical Significance 0.008 Supporting Reference Compounds 308 E-value 62.3572
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.357 Applicability Domain 0.857 Statistical Significance 0.0199 Supporting Reference Compounds 524 E-value 154.686
Click to view 3D structure	Vacuolar protein sorting-associated protein 4B	O75351	Humans	Predicted (SEA)	Prediction Confidence Score 0.353 Applicability Domain 0.353 Statistical Significance 6.00e-05 Supporting Reference Compounds 1 E-value 0.467095
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.46 Statistical Significance 0.0363 Supporting Reference Compounds 823 E-value 282.982
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	Prediction Confidence Score 0.324 Applicability Domain 0.46 Statistical Significance 0.0106 Supporting Reference Compounds 225 E-value 82.5202
Click to view 3D structure	Adhesion G-protein coupled receptor F1	Q5T601	Humans	Predicted (SEA)	Prediction Confidence Score 0.313 Applicability Domain 0.857 Statistical Significance 2.00e-05 Supporting Reference Compounds 24 E-value 0.155698
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 0.46 Statistical Significance 0.0435 Supporting Reference Compounds 686 E-value 338.956
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.299 Applicability Domain 0.394 Statistical Significance 0.0317 Supporting Reference Compounds 297 E-value 247.016
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.295 Applicability Domain 0.339 Statistical Significance 0.0499 Supporting Reference Compounds 536 E-value 388.779
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.29 Applicability Domain 0.339 Statistical Significance 0.102 Supporting Reference Compounds 955 E-value 794.218
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.279 Applicability Domain 0.305 Statistical Significance 0.083 Supporting Reference Compounds 593 E-value 646.382
Click to view 3D structure	Tyrosine-protein kinase JAK3	P52333	Humans	Predicted (SEA)	Prediction Confidence Score 0.279 Applicability Domain 0.328 Statistical Significance 0.1871 Supporting Reference Compounds 961 E-value 1456.71
Click to view 3D structure	Tyrosine-protein kinase JAK2	O60674	Humans	Predicted (SEA)	Prediction Confidence Score 0.279 Applicability Domain 0.328 Statistical Significance 0.1947 Supporting Reference Compounds 1022 E-value 1515.41
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	Prediction Confidence Score 0.279 Applicability Domain 0.328 Statistical Significance 0.1492 Supporting Reference Compounds 763 E-value 1161.9
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.31 Statistical Significance 0.0682 Supporting Reference Compounds 380 E-value 531.087
Click to view 3D structure	5-hydroxytryptamine receptor 1F	P30939	Humans	Predicted (SEA)	Prediction Confidence Score 0.272 Applicability Domain 0.46 Statistical Significance 0.0073 Supporting Reference Compounds 45 E-value 57.1413
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Known	Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT_1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT_1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT_1B receptor agonism.
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Known	Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT_1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT_1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT_1B receptor agonism.

Concentrations

Not Available

External Links

DrugBank ID

DB00998

HMDB ID

HMDB0015133

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Samir Naik, Anthony Crasto, Narendra Joshi, Sachin Srivastava, “Amorphous frovatriptan succinate and process for the preparation thereof.” U.S. Patent US20070299123, issued December 27, 2007.

MSDS

Not Available

General References

Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [PubMed: 11735616]
Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [PubMed: 15311727]
Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [PubMed: 18001261]
Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [PubMed: 18360605]
Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [PubMed: 15342617]
Jhee SS, Shiovitz T, Crawford AW, Cutler NR: Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review. Clin Pharmacokinet. 2001;40(3):189-205. [PubMed: 11327198]
Drugs.com - http://www.drugs.com/cons/Frovatriptan.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Frovatriptan (CED0010031)

Structure for CHEM002317: Frovatriptan

Structure