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HCID 77992Erstellt: 3. November 2026

Frovatriptan

Sb 209509 · Hsdb 7363 · FROVATRIPTAN · Iloperidone-d · R-Frovatriptan · Unii-H82Q2D5wa7 · Frovatriptan 13CD3 · 1H-Carbazole-6-carboxamide, 2,3,4,9-tetrahydro-3-(methylamino)-, (R)-

https://huagongshe.com/de/chemical/77992

Molekülstruktur von Frovatriptan

Identifikatoren & physikalische Daten

CAS No.158747-02-5
SummenformelC14H17N3O
Durchschnittliche Molmasse243,3 g/mol
Monoisotopische Masse243,13716216 g/mol
SMILESCN[C@@H]1CCc2[nH]c3ccc(C(N)=O)cc3c2C1
InChIKeyXPSQPHWEGNHMSK-SECBINFHSA-N
PubChem CID77992
ChEMBLCHEMBL1279
ChEBICHEBI:134991
DTXSIDDTXSID0023080

Chemische & physikalische Eigenschaften

XLogP1,2
Polarare Oberfläche (TPSA)70,9
H-Brücken-Donoren3
H-Brücken-Akzeptoren2
Frei drehbare Bindungen2
Schwere Atome18
Formalladung0
Komplexität333
ArzneimittelPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)0.9
LöslichkeitSoluble1.23e-01 g/L
Human DrugsBreast FeedingLactationMilk, HumanSerotonin Receptor AgonistsSerotonin 5-HT1 Receptor AgonistsTriptansVasoconstrictor Agents
Physical DescriptionSolid
Other Experimental PropertiesMW = 379.4 ... white to off-white powder ... soluble in water /Succinate/
Siedepunkt515.2±50.0 °C(Predicted)
Dichte1.27±0.1 g/cm3(Predicted)
pKa (Säurekonstante)16.39±0.40(Predicted)

Sicherheit & Vorschriften

FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl frovatriptan succinate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Frovatriptan Succinate/
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
TreatmentAs 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. (L1712)
WechselwirkungenConcurrent use /of frovatriptan/ with oral contraceptives has resulted in a 30% increase in the area under the plasma concentration-time curve (AUC) and peak plasma concentration of frovatriptan.Concurrent use /of frovatriptan/ with ergotamine tartrate has resulted in a 25% decrease in the area under the plasma concentration-time curve (AUC) and peak plasma concentration of frovatriptan.Concurrent use /of frovatriptan with selective serotonin reuptake inhibitors, such as: fluoxetine, fluvoxamine, paroxetine or sertraline/ may result in weakness, hyperreflexia, and incoordinationcareful observation of the patients is recommended.Concurrent use /of frovatriptan/ with propranolol increased the area under the plasma concentration-time curve (AUC) in males by 60% and in females by 29%. the peak plasma concentration was increased by 23% in males and 16% in femaleshowever the half-life of frovatriptan in both populations, though slightly longer in females was not affected by concomitant administration of propranolol.A delay of 24 hours between administration of dihydroergotamine, ergotamine, or methylsergide or other 5-hydroxytryptamine agonists and frovatriptan is recommended because of the possibility of additive and/or prolonged vasoconstriction.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6200(SRC), determined from a structure estimation method(2), indicates that frovatriptan is expected to be immobile in soil(SRC). An estimated pKa value of 10.6 (secondary amine)(3) indicates that frovatriptan will exist primarily as a cation in the environment. Volatilization of frovatriptan from moist soil surfaces is not expected to be an important fate process(SRC) because cations do not volatilize. Frovatriptan is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6200(SRC), determined from a structure estimation method(2), indicates that frovatriptan is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa value of 10.6 (secondary amine)(3) indicates that frovatriptan will primarily exist in cation form in the environment. Volatilization from water surfaces is not expected(SRC) because cations do not volatilize. According to a classification scheme(4), an estimated BCF of 2(SRC), from an estimated log Kow of 1.3(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), frovatriptan, which has an estimated vapor pressure of 3.7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase frovatriptan may be removed from the air by wet or dry deposition(SRC). Frovatriptan contains the indole chromophore which absorbs at wavelengths > 290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
ExpositionspfadeFrovatriptan is rapidly absorbed from the duodenum, but has low oral bioavailability.
Milk ConcentrationsIt is not known whether frovatriptan is distributed into human breast milk. However, frovatriptan is distributed into the milk of lactating rats with the maximum concentration being four times higher than that seen in blood.
ToxizitätsübersichtThree distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT<sub>1D</sub> receptors, which serves to inhibit both dural vasodilation and inflammation(2) direct inhibition of trigeminal nuclei cell excitability via 5-HT<sub>1B/1D</sub> receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT<sub>1B</sub> receptor agonism.
Signs and SymptomsThere 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.
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of frovatriptan can be estimated to be 6200(SRC). According to a classification scheme(2), this estimated Koc value suggests that frovatriptan is expected to be immobile in soil. An estimated pKa value of 10.6 (secondary amine)(3) indicates that frovatriptan will exist primarily as a cation in the environment and cations generally adsorb to soil and sediment more strongly than their neutral counterparts(4).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Cerebral hemorrhage, subarachnoid hemorrhage, stroke and other cerebrovascular events have been reported in patients treated with 5-HT1 agonistsand some have resulted in fatalities. In a number of cases, it appears possible that the cerebrovascular events were primary, the agonist having been administered in the incorrect belief that the symptoms experienced were a consequence of migraine, when they were not. It should be noted that patients with migraine may be at increased risk of certain cerebrovascular events (e.g. stroke, hemorrhage, transient ischemic attack)./SIGNS AND SYMPTOMS/ Risk of coronary vasospasm, myocardial ischemia and/or infarction, life-threatening cardiac rhythm disturbances, and death associated with use of 5-HT1 receptor agonists. Use of frovatriptan not recommended in patients with known or suspected ischemic or vasospastic heart disease (see Cautions: Contraindications) or in patients in whom unrecognized coronary artery disease is likely (e.g., postmenopausal women, men older than 40 years of age, patients with risk factors such as hypertension, hypercholesterolemia, smoking, obesity, diabetes, family history of coronary artery disease) unless a prior cardiovascular evaluation provides satisfactory evidence that the patient does not have coronary artery disease, ischemic heart disease, or other underlying cardiovascular disease.
Artificial Pollution SourcesFrovatriptan's production and use as a drug for the treatment of migraine headaches(1) may result in its release to the environment through various waste streams(SRC).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)frovatriptanDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022
Gefahrstoffdaten158747-02-5(Hazardous Substances Data)