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HCID 3348Erstellt: 4. November 2026

Fexofenadine

Carnipure tartrate · Methyl 4-[4-[4-(Hydroxy Diphenyl Methyl)-1-Piperidinyl]-1-Oxobutyl]-A,A-Dimethyl Phenylacetate · FEX-12 · mdl16455 · FEXOFENADINE · Fexafenadine · Fexofenadine-D5 · Fexofenadinebase

https://huagongshe.com/de/chemical/3348

Molekülstruktur von Fexofenadine

Identifikatoren & physikalische Daten

CAS No.83799-24-0
SummenformelC32H39NO4
Durchschnittliche Molmasse501,7 g/mol
Monoisotopische Masse501,28790873 g/mol
SMILESCC(C)(C(=O)O)c1ccc(C(O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1
InChIKeyRWTNPBWLLIMQHL-UHFFFAOYSA-N
PubChem CID3348
ChEMBLCHEMBL914
ChEBICHEBI:5050
EC No.801-893-7
DTXSIDDTXSID00861411

Chemische & physikalische Eigenschaften

XLogP3
Polarare Oberfläche (TPSA)81
H-Brücken-Donoren3
H-Brücken-Akzeptoren5
Frei drehbare Bindungen10
Schwere Atome37
Formalladung0
Komplexität678
StoffklassenPharmaceutical
ArzneimittelPharmaceuticalsPharmaceuticals -> Used in Switzerland
Color/FormCrystals from methanol-butanone
LöslichkeitSlightly solubleMethanol (Slightly, Heated, Sonicated)
Human DrugsBreast FeedingLactationMilk, HumanAntihistaminesNonsedating AntihistaminesPharmaceuticalsAntiallergics and medicines used in anaphylaxis
Schmelzpunkt195-197 °C142.5 °C218-220°C
Physical DescriptionSolid
Stability/Shelf LifeCommercially available fexofenadine hydrochloride capsules have an expiration date of 18 or 24 months after the date of manufacture when packaged in the manufacturer's unopened blister packages or high-density polyethylene bottles, respectively. Commercially available fexofenadine hydrochloride 30-mg conventional tablets have an expiration date of 18 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles, whereas the commercially available fexofenadine hydrochloride 60-mg conventional tablets have an expiration date of 30 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles. In addition, fexofenadine hydrochloride 180-mg conventional tablets have an expiration date of 18 or 30 months after the date of manufacture when packaged either in the manufacturer's unopened blister packages or high-density polyethylene bottles, respectively.
Collision Cross Section226.9 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]225.55 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental PropertiesMolecular weight is 538.13. Fexofenadine hydrochloride is a white to off-white crystalline powder. It is freely soluble in methanol and ethanol, slightly soluble in chloroform and water, and insoluble in hexane. Fexofenadine hydrochloride is a racemate and exists as a zwitterion in aqueous media at physiological pH /Hydrochloride/
Siedepunkt697.3±55.0 °C(Predicted)
Dichte1.171±0.06 g/cm3(Predicted)
LagerbedingungenSealed in dry,Store in freezer, under -20°C
AggregatzustandSolid
pKa (Säurekonstante)4.43±0.10(Predicted)
FarbeWhite to Off-White
BCS Class1,3
LogP (Verteilungskoeffizient)2.81
CAS Datenbank83799-24-0(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungNot Classified
Regulatorische InformationenStatus: Active Update: 13-03-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/7116
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fexofenadine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /fexofenadine hydrochloride/
Hazard Classes and CategoriesNot Classified
LagerbedingungenFexofenadine hydrochloride capsules, conventional tablets, and the extended-release tablets containing fexofenadine hydrochloride in fixed combination with pseudoephedrine hydrochloride should be stored at controlled room temperature between 20-25 °Cfoil-backed blister packages containing the drug should be protected from excessive moisture.
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
TreatmentIn the event of overdose, consider standard measures to remove any unabsorbed drug. Symptomatic and supportive treatment is recommended. (L1712)
WechselwirkungenIncreased concentrations of fexofenadine have been reported in 2 controlled drug interaction studies in healthy individuals receiving 120 mg of fexofenadine hydrochloride twice daily concomitantly with erythromycin dosages of 500 mg every 8 hours or ketoconazole 400 mg once daily. In these studies, area under the plasma-concentration time curve (AUC) of fexofenadine increased by 109 or 164% following concomitant administration with erythromycin or ketoconazole, respectively, while peak plasma concentrations of fexofenadine increased by 82 or 135%, respectively. However, no clinically important adverse effects or changes in the QT interval corrected for rate (QTc) were reported after concomitant administration of erythromycin or ketoconazole with fexofenadine.Administration of a single 120-mg dose (2 capsules of 60 mg) of fexofenadine hydrochloride within 15 minutes of administration of an aluminum and magnesium hydroxides antacid (Maalox) decreased the AUC and peak plasma concentration of fexofenadine by 41 and 43%, respectively. Therefore, the manufacturer states that fexofenadine (alone or in fixed combination with pseudoephedrine hydrochloride) should not be taken closely in time with antacids containing aluminum and magnesium.

Anwendungen & Verwendung

Beschreibung

Fexofenadine, the carboxylic acid metabolite of terfenadine, is widely available. It accounts for the antihistaminic properties of terfenadine, which is very rapidly metabolized via CYP3A4-catalyzed processes. Members of the organic anion transporter protein family and the drug efflux transporter P-glycoprotein are involved in the disposition of fexofenadine. Fexofenadine does not have the antiarrhythmic side effects of terfenadine.

Verwenden

A metabolite of of terfenadine, a H1-Histamine receptor antagonist

Fruit (grapefruit, orange, apple) juices may reduce bioavailability and systemic exposure of fexofenadine. In clinical studies, the size of wheal and flare was substantially larger when fexofenadine hydrochloride was administered with grapefruit juice or orange juice compared with water
based on literature reports, the same effects may be extrapolated to other fruit juices such as apple juice. The clinical importance of these observations is unknown. Based on a population pharmacokinetic analysis of combined data from the studies using concomitant grapefruit juice or orange juice with data from a bioequivalence study, bioavailability of fexofenadine was reduced by 36%. Therefore, to maximize the effects of fexofenadine, the manufacturer recommends that the drug be administered with water.
HepatotoxicityFexofenadine use is not generally associated with liver enzyme elevations but terfenadine, a second generation antihistamine that is metabolized in part to fexofenadine, was the attributed cause of several reported cases of clinically apparent liver injury. Terfenadine was also linked to cardiac arrhythmias and prolongation of the QTc interval for which reason it was withdrawn from use in 1997, just as fexofenadine was introduced. Liver injury from terfenadine typically arose after 1 to 5 months and was associated with a hepatocellular pattern of liver enzyme abnormalities without immunoallergic or autoimmune features. Fexofenadine has not been linked to similar cases of cardiac arrhythmias or liver injury.
Unerwünschte WirkungenThe most common dose-dependent adverse drug reactions associated with fexofenadine include drowsiness, fatigue, and dry mouth. In addition, post-marketing surveillance has reported rare occurrences of Stevens-Johnson syndrome or toxic epidermal necrolysis induced by fexofenadine.
ExpositionspfadeOral. 33%
Milk ConcentrationsIt is not known if fexofenadine hydrochloride is distributed into breast milk
ToxizitätsübersichtSigns and Symptoms of OverdoseLike other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects.
Signs and SymptomsSide effects include dizziness, drowsiness, and dry mouth.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)fexofenadineDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ No evidence of carcinogenesis was seen in mice and rats receiving oral terfenadine (the parent drug of fexofenadineno longer commercially available in the US) dosages up to 150 mg/kg daily for 18 and 24 months, respectively, resulting in fexofenadine exposure levels calculated to be of 2-3 times the maximum recommended daily oral human dosage.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in rats and rabbits using oral terfenadine dosages up to 300 mg/kg resulting in fexofenadine exposure levels calculated to be about 3-4 and 25-31 times, respectively, those resulting from the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults have not revealed evidence of teratogenicity.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in mice receiving fexofenadine doses up to 3730 mg/kg (approximately 10-15 times the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults) have not revealed evidence of adverse or teratogenic effects during gestation.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproduction studies in male and female mice receiving fexofenadine doses up to 4438 mg/kg (approximately 10-15 times the maximum recommended daily oral human dosage of fexofenadine hydrochloride in adults) have not revealed evidence of impaired fertility. Reproduction studies in rats using terfenadine dosages of 150 mg/kg (resulting in fexofenadine exposure levels calculated to be about 3-4 times those resulting from the maximum recommended daily oral human dosage of fexofenadine hydrochloride), revealed dose-related decreases in implantation and an increased incidence of postimplantation losses.[McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 34]For more Non-Human Toxicity Excerpts (Complete) data for FEXOFENADINE (6 total), please visit the HSDB record page.
Populations at Special RiskSafety and efficacy of fexofenadine hydrochloride have not been established in children younger than 6 years of age.
Gefahrstoffdaten83799-24-0(Hazardous Substances Data)