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QuickView for Terfenadine (compound)


PubChem
Name: Terfenadine
PubChem Compound ID: 5405
Description: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.
Molecular formula: C32H41NO2
Molecular weight: 471.673 g/mol
Synonyms:
RMI-9918; Seldane (TN); MDL 9918; Triludan; DivK1c_001011; alpha-(p-tert-Butylphenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; Terfenadine (JAN/USAN); alpha-(4-(1,1-Dimethylethyl)phenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; NSC665802; Nebralin.
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DrugBank
Identification
Name: Terfenadine
Name (isomeric): DB00342
Drug Type: small molecule
Description: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.
Synonyms:
Ternadin
Brand: Allerplus, Terdin, Teldanex, Cyater, Seldane, Aldaban, Terfex, Teldane, Triludan
Category: Antihistamines, Antiarrhythmic Agents, Anti-Allergic Agents, Histamine H1 Antagonists, Non-Sedating
CAS number: 50679-08-8
Pharmacology
Indication: For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
Pharmacology: Terfenadine, an H1-receptor antagonist antihistamine, is similar in structure to astemizole and haloperidol, a butyrophenone antipsychotic. The active metabolite of terfenadine is fexofenadine.
Mechanism of Action:
Terfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS dep...
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Absorption: On the basis of a mass balance study using 14C labeled terfenadine the oral absorption of terfenadine was estimated to be at least 70%
Protein binding: 70%
Biotransformation: Hepatic
Half Life: 3.5 hours
Toxicity: Mild (e.g., headache, nausea, confusion), but adverse cardiac events including cardiac arrest, ventricular arrhythmias including torsades de pointes and QT prolongation have been reported. LD50=mg/kg (orally in mice)
Affected organisms: Humans and other mammals
Interactions
Drug interaction:
FosamprenavirIncreased risk of cardiotoxicity and arrhythmias
ErythromycinIncreased risk of cardiotoxicity and arrhythmias
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
TrimipramineIncreased risk of cardiotoxicity and arrhythmias
TelithromycinIncreased risk of cardiotoxicity and arrhythmias
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