terfenadine

E850017

Terfenadine is a withdrawn second-generation antihistamine formerly used to treat allergy symptoms but discontinued due to its risk of causing serious cardiac arrhythmias.

All labels observed (1)

Label Occurrences
terfenadine canonical 1

How this entity was disambiguated

Statements (50)

Predicate Object
instanceOf H1 receptor antagonist
piperidine derivative
second-generation antihistamine
withdrawn drug
actsOn histamine H1 receptor
affectsIonChannel hERG potassium channel
belongsToATCClass R06AX12
contraindicatedWith CYP3A4 inhibitors
clarithromycin
erythromycin
grapefruit juice
itraconazole
ketoconazole
crossesBloodBrainBarrier minimally
developedBy Marion Merrell Dow
hasActiveMetabolite fexofenadine
hasAdverseEffect cardiac arrhythmia
dizziness
dry mouth
headache
palpitations
sedation (low incidence)
syncope
hasBioavailability low due to first-pass metabolism
hasCASNumber 50679-08-8
hasDrugBankID DB00342
hasIUPACName (±)-4-[1-(4-tert-butylphenyl)-4-(hydroxydiphenylmethyl)piperidin-4-ylidene]butanoic acid
hasLogP high lipophilicity
hasMeltingPoint 150-153 °C (approximate)
hasMolecularFormula C32H41NO2
hasPharmacologicalEffect anti-allergic effect
antihistamine effect
hasProteinBinding high
hasPubChemCID 5405
hasRisk QT interval prolongation
sudden cardiac death
torsades de pointes
ventricular arrhythmia
hasUNIIs 0H73WJJ391
introducedIn 1980s
isProdrugOf fexofenadine
metabolizedBy CYP3A4
routeOfAdministration oral
usedFor allergic rhinitis
chronic idiopathic urticaria
seasonal allergic rhinitis
withdrawnFromMarketIn European Union
United States
withdrawnIn 1990s
withdrawnReason risk of serious cardiac arrhythmias

How these facts were elicited

Referenced by (1)

Full triples — surface form annotated when it differs from this entity's canonical label.

CYP2J2 metabolizes terfenadine