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药品详细

Terfenadine(特非那定)

化学结构式图
中文名
特非那定
英文名
Terfenadine
分子式
C32H41NO2
化学名
1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol
分子量
Average: 471.6734
Monoisotopic: 471.313729561
CAS号
50679-08-8
ATC分类
R06A 未知
药物类型
small molecule
阶段
approved, withdrawn
商品名
同义名
基本介绍

In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.

生产厂家
    封装厂家
    • Pharmaceutical Utilization Management Program VA Inc.
    • Pharmedix
    • Veratex Corp.
    参考
    Synthesis Reference Not Available
    General Reference Not Available
    剂型
    规格
    化合物类型
    Type small molecule
    Classes
    • Diphenylmethanes
    Substructures
    • Hydroxy Compounds
    • Benzyl Alcohols and Derivatives
    • Benzene and Derivatives
    • Cumenes and Derivatives
    • Aliphatic and Aryl Amines
    • Alcohols and Polyols
    • Diphenylmethanes
    • Heterocyclic compounds
    • Aromatic compounds
    • Piperidines
    适应症
    药理
    Indication For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
    Pharmacodynamics 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 depression is minimal.
    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%
    Volume of distribution Not Available
    Protein binding 70%
    Metabolism
    Hepatic

    Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

    Substrate Enzymes Product
    Terfenadine
    		fexofenadine Details
    Route of elimination Not Available
    Half life 3.5 hours
    Clearance Not Available
    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
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 147 °C PhysProp
    water solubility 0.0963 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001)
    logP 7.1 Not Available
    Predicted Properties
    Property Value Source
    water solubility 4.58e-04 g/l ALOGPS
    logP 5.89 ALOGPS
    logP 6.48 ChemAxon
    logS -6 ALOGPS
    pKa (strongest acidic) 13.2 ChemAxon
    pKa (strongest basic) 9.02 ChemAxon
    physiological charge 1 ChemAxon
    hydrogen acceptor count 3 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 43.7 ChemAxon
    rotatable bond count 9 ChemAxon
    refractivity 146.27 ChemAxon
    polarizability 56.45 ChemAxon
    药物相互作用
    Drug Interaction
    Acetophenazine Increased risk of cardiotoxicity and arrhythmias
    Amiodarone Increased risk of cardiotoxicity and arrhythmias
    Amitriptyline Increased risk of cardiotoxicity and arrhythmias
    Amoxapine Increased risk of cardiotoxicity and arrhythmias
    Amprenavir Increased risk of cardiotoxicity and arrhythmias
    Aprepitant Increased risk of cardiotoxicity and arrhythmias
    Bepridil Increased risk of cardiotoxicity and arrhythmias
    Chlorpromazine Increased risk of cardiotoxicity and arrhythmias
    Cimetidine Increased risk of cardiotoxicity and arrhythmias
    Cisapride Increased risk of cardiotoxicity and arrhythmias
    Clarithromycin Increased risk of cardiotoxicity and arrhythmias
    Clomipramine Increased risk of cardiotoxicity and arrhythmias
    Delavirdine Increased risk of cardiotoxicity and arrhythmias
    Desipramine Increased risk of cardiotoxicity and arrhythmias
    Diltiazem Increased risk of cardiotoxicity and arrhythmias
    Disopyramide Increased risk of cardiotoxicity and arrhythmias
    Doxepin Increased risk of cardiotoxicity and arrhythmias
    Efavirenz Increased risk of cardiotoxicity and arrhythmias
    Erythromycin Increased risk of cardiotoxicity and arrhythmias
    Flecainide Increased risk of cardiotoxicity and arrhythmias
    Fluconazole Increased risk of cardiotoxicity and arrhythmias
    Fluoxetine Increased risk of cardiotoxicity and arrhythmias
    Fluphenazine Increased risk of cardiotoxicity and arrhythmias
    Fluvoxamine Increased risk of cardiotoxicity and arrhythmias
    Fosamprenavir Increased risk of cardiotoxicity and arrhythmias
    Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
    Imipramine Increased risk of cardiotoxicity and arrhythmias
    Indinavir Increased risk of cardiotoxicity and arrhythmias
    Itraconazole Increased risk of cardiotoxicity and arrhythmias
    Josamycin Increased risk of cardiotoxicity and arrhythmias
    Ketoconazole Increased risk of cardiotoxicity and arrhythmias
    Mesoridazine Increased risk of cardiotoxicity and arrhythmias
    Methdilazine Increased risk of cardiotoxicity and arrhythmias
    Methotrimeprazine Increased risk of cardiotoxicity and arrhythmias
    Mexiletine Increased risk of cardiotoxicity and arrhythmias
    Mibefradil Increased risk of cardiotoxicity and arrhythmias
    Nefazodone Increased risk of cardiotoxicity and arrhythmias
    Nelfinavir Increased risk of cardiotoxicity and arrhythmias
    Nicardipine Increased risk of cardiotoxicity and arrhythmias
    Nortriptyline Increased risk of cardiotoxicity and arrhythmias
    Perphenazine Increased risk of cardiotoxicity and arrhythmias
    Posaconazole Contraindicated co-administration
    Procainamide Increased risk of cardiotoxicity and arrhythmias
    Prochlorperazine Increased risk of cardiotoxicity and arrhythmias
    Promazine Increased risk of cardiotoxicity and arrhythmias
    Promethazine Increased risk of cardiotoxicity and arrhythmias
    Propafenone Increased risk of cardiotoxicity and arrhythmias.
    Propericiazine Increased risk of cardiotoxicity and arrhythmias
    Propiomazine Increased risk of cardiotoxicity and arrhythmias
    Protriptyline Increased risk of cardiotoxicity and arrhythmias
    Quinidine Increased risk of cardiotoxicity and arrhythmias
    Quinine Increased risk of cardiotoxicity and arrhythmias
    Quinupristin This combination presents an increased risk of toxicity
    Ritonavir Increased risk of cardiotoxicity and arrhythmias
    Saquinavir Increased risk of cardiotoxicity and arrhythmias
    Sotalol Increased risk of cardiotoxicity and arrhythmias
    Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
    Telavancin Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
    Telithromycin Increased risk of cardiotoxicity and arrhythmias
    Thiethylperazine Increased risk of cardiotoxicity and arrhythmias
    Thioridazine Increased risk of cardiotoxicity and arrhythmias
    Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Terfenadine. Concomitant therapy is contraindicated.
    Tocainide Increased risk of cardiotoxicity and arrhythmias
    Trifluoperazine Increased risk of cardiotoxicity and arrhythmias
    Triflupromazine Increased risk of cardiotoxicity and arrhythmias
    Trimeprazine Increased risk of cardiotoxicity and arrhythmias
    Trimipramine Increased risk of cardiotoxicity and arrhythmias
    Troleandomycin Increased risk of cardiotoxicity and arrhythmias
    Verapamil Increased risk of cardiotoxicity and arrhythmias
    Voriconazole Increased risk of cardiotoxicity and arrhythmias
    食物相互作用
    Not Available

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