ContaminantDB: Frovatriptan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (27)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:08 UTC

Update Date

2026-05-14 16:55:21 UTC

Accession Number

CHEM002317

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 Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

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

Pathways

Name	SMPDB Link	KEGG Link
Frovatriptan Mechanism of Action Action Pathway	SMP0126999	Not Available
Frovatriptan Drug Metabolism Action Pathway	SMP0143428	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-3690000000-20d2133e95fbc6b1f414	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-fc527e672048d9bf866c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0490000000-09182e67659519af87e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0l1i-0910000000-81f4aa818323e96b5464	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-bd79ad698f8bd9fbb84b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2490000000-4632cbf11a6dc353d2cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-948170ac23122892a5ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-168fda82142bf345541b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0090000000-3dac4efa84856ab16486	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0910000000-bdfabb283d321aa1d9e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-932ee60351365d51e611	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1190000000-c3fd5753f8f9a8a098eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-4910000000-8fac1192455fd2253b72	Spectrum

Toxicity Profile

Route of Exposure

Frovatriptan is rapidly absorbed from the duodenum, but has low oral bioavailability.

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.

Metabolism

In vitro, cytochrome P450 1A2 appears to be the principal enzyme involved in the metabolism of frovatriptan to several metabolites including hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, and several other minor metabolites. Desmethyl frovatriptan has lower affinity for 5-HT_1B/1D receptors compared to the parent compound. The N-acetyl desmethyl metabolite has no significant affinity for 5-HT receptors. The activity of the other metabolites is unknown. Route of Elimination: Radiolabeled compounds excreted in urine were unchanged frovatriptan, hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, together with several other minor metabolites. Less than 10% of frovatriptan was excreted in urine after an oral dose. Half Life: 26 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

For the acute treatment of migraine attacks with or without aura in adults.

Minimum Risk Level

Not Available

Health Effects

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)

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

1. 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.

2. Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8.

3. Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705.

4. Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65.

5. Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33.

6. 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.

Frovatriptan (CHEM002317)

Structure for CHEM002317: Frovatriptan