药品详细

Terbinafine(特比萘芬)

基本信息
剂型规格
适应症
药理
临床
理化性质
相互作用
文档
专利
Pathway
文献
序列

化学结构式图

中文名

特比萘芬

英文名

Terbinafine

分子式

C₂₁H₂₅N

化学名

(6,6-dimethylhept-2-en-4-yn-1-yl)(methyl)(naphthalen-1-ylmethyl)amine

分子量

Average: 291.4299
Monoisotopic: 291.198699805

CAS号

91161-71-6

ATC分类

D01A 未知;D01B 未知

药物类型

small molecule

阶段

approved

商品名

同义名

基本介绍

Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting the fungal squalene monooxygenase (squalene 2,3-epoxidase), an enzyme that is part of the fungal cell wall synthesis pathway.

生产厂家

Apotex corp
Aurobindo pharma ltd
Breckenridge pharmaceutical inc
Dr reddys laboratories inc
Gedeon richter usa inc
Genpharm inc
Glenmark generics ltd
Harris pharmaceutical inc
Invagen pharmaceuticals inc
Mylan pharmaceuticals inc
Novartis consumer health inc
Novartis pharmaceuticals corp
Orchid healthcare
Roxane laboratories inc
Taro pharmaceuticals usa inc
Teva pharmaceuticals usa inc
Watson laboratories inc
Wockhardt ltd

封装厂家

Actavis Group
Apotex Inc.
A-S Medication Solutions LLC
Aurobindo Pharma Ltd.
Blu Pharmaceuticals LLC
Bryant Ranch Prepack
Camber Pharmaceuticals Inc.
Cipla Ltd.
CVS Pharmacy
Diversified Healthcare Services Inc.
Doctor Reddys Laboratories Ltd.
Glenmark Generics Ltd.
Harris Pharmaceutical Inc.
InvaGen Pharmaceuticals Inc.
JSJ Pharmaceuticals Inc.
Kaiser Foundation Hospital
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Northstar Rx LLC
Novartis AG
Orchid Healthcare
Patheon Inc.
Pharmacy Service Center
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Rebel Distributors Corp.
Resource Optimization and Innovation LLC
Roxane Labs
Sandoz
Southwood Pharmaceuticals
Sunmark
Target Corp.
Teva Pharmaceutical Industries Ltd.
The Jay Group Inc.
Wockhardt Ltd.

参考

Synthesis Reference

Not Available

General Reference

Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. Pubmed
Klobucnikova V, Kohut P, Leber R, Fuchsbichler S, Schweighofer N, Turnowsky F, Hapala I: Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene. Biochem Biophys Res Commun. 2003 Sep 26;309(3):666-71. Pubmed
Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. Pubmed
Birnbaum JE: Pharmacology of the allylamines. J Am Acad Dermatol. 1990 Oct;23(4 Pt 2):782-5. Pubmed
McClellan KJ, Wiseman LR, Markham A: Terbinafine. An update of its use in superficial mycoses. Drugs. 1999 Jul;58(1):179-202. Pubmed
Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. Pubmed
Gianni C: Update on antifungal therapy with Terbinafine. G Ital Dermatol Venereol. 2010 Jun;145(3):415-23. Pubmed
Korting HC, Kiencke P, Nelles S, Rychlik R: Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis. Am J Clin Dermatol. 2007;8(6):357-64. Pubmed

剂型

规格

化合物类型

Type	small molecule

Classes

Naphthalenes

Substructures

Alkanes and Alkenes
Naphthalenes
Alkynes
Benzene and Derivatives
Aliphatic and Aryl Amines
Aromatic compounds

适应症

药理

Indication

For the treatment of dermatophyte infections of the toenail or fingernail caused by susceptible fungi. Also for the treatment of tinea capitis (scalp ringworm) and tinea corporis (body ringworm) or tinea cruris (jock itch).

Pharmacodynamics

Terbinafine is an allylamine antifungal agent and acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. In vitro, mammalian squalene monooxygenase (squalene 2,3-epoxidase) is only inhibited at higher (4000 fold) concentrations than is needed for inhibition of the dermatophyte enzyme. Depending on the concentration of the drug and the fungal species test in vitro, Terbinafine may be fungicidal. However, the clinical significance of in vitro data is unknown.

Mechanism of action

Terbinafine is hypothesized to act by inhibiting squalene monooxygenase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. This inhibition also results in an accumulation of squalene, which is a substrate catalyzed to 2,3-oxydo squalene by squalene monooxygenase. The resultant high concentration of squalene and decreased amount of ergosterol are both thought to contribute to terbinafine's antifungal activity.

Absorption

Readily absorbed from gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

>99%

Metabolism

Hepatic

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

Substrate	Enzymes	Product
Terbinafine	Cytochrome P450 2C9 Cytochrome P450 2C8 Cytochrome P450 1A2 Cytochrome P450 2C19	Hydroxyterbinafine	Details
Terbinafine	Cytochrome P450 2C9 Cytochrome P450 2C8 Cytochrome P450 1A2	N-Desmethylterbinafine	Details
Terbinafine	Cytochrome P450 3A4	1-Naphtaldehyde	Details

Route of elimination

Prior to excretion, terbinafine is extensively metabolized.

Half life

36 hours

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Fungi

Pathways

Not Available

理化性质

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	195-198 °C	Not Available
water solubility	Slightly soluble	Not Available
logP	5.9	Not Available

Predicted Properties

Property	Value	Source
water solubility	7.38e-04 g/l	ALOGPS
logP	5.51	ALOGPS
logP	5.53	ChemAxon
logS	-5.6	ALOGPS
pKa (strongest basic)	8.94	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	3.24	ChemAxon
rotatable bond count	6	ChemAxon
refractivity	98.08	ChemAxon
polarizability	35.83	ChemAxon

药物相互作用

Drug	Interaction
Aminophylline	Terbinafine increases the effect and toxicity of theophylline
Amitriptyline	Terbinafine may reduce the metabolism and clearance of Amitryptyline. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Terbinafine is initiated, discontinued or dose changed.
Amoxapine	Terbinafine may reduce the metabolism and clearance of Amoxapine. Consider alternate therapy or monitor for therapeutic/adverse effects of Amoxapine if Terbinafine is initiated, discontinued or dose changed.
Aripiprazole	Terbinafine may reduce the metabolism and clearance of Aripiprazole. Consider alternate therapy or monitor for therapeutic/adverse effects of Aripiprazole if Terbinafine is initiated, discontinued or dose changed.
Atomoxetine	Terbinafine, a CYP2D6 inhibitor, may reduce the metabolism and clearance of Atomoxetine. Consider alternate therapy or monitor for therapeutic/adverse effects of Atomoxetine if Terbinafine is initiated, discontinued or dose changed.
Caffeine	Terbinafine may increase the plasma concentration of Caffeine.
Captopril	Terbinafine may reduce the metabolism and clearance of Captopril. Consider alternate therapy or monitor for therapeutic/adverse effects of Captopril if Terbinafine is initiated, discontinued or dose changed.
Carvedilol	Terbinafine may reduce the metabolism and clearance of Carvedilol. Consider alternate therapy or monitor for therapeutic/adverse effects of Carvedilol if Terbinafine is initiated, discontinued or dose changed.
Chloroquine	Terbinafine may reduce the metabolism and clearance of Chloroquine. Consider alternate therapy or monitor for therapeutic/adverse effects of Chloroquine if Terbinafine is initiated, discontinued or dose changed.
Chlorpromazine	Terbinafine may reduce the metabolism and clearance of Chlorpromazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Chlorpromazine if Terbinafine is initiated, discontinued or dose changed.
Clomipramine	Terbinafine may reduce the metabolism and clearance of Clomipramine. Consider alternate therapy or monitor for therapeutic/adverse effects of Clomipramine if Terbinafine is initiated, discontinued or dose changed.
Codeine	Terbinafine may decrease the efficacy of Codeine by inhibiting active metabolite production. Consider an alternate analgesic or monitor for effectiveness of Codeine.
Cyclosporine	Terbinafine may decrease the plasma concentration and therapeutic effect of cyclosporine.
Desipramine	Terbinafine may increase the effect and toxicity of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of desipramine if terbinafine is initiated, discontinued or dose changed.
Dextromethorphan	Terbinafine may reduce the metabolism and clearance of Dextromethorphan. Consider alternate therapy or monitor for therapeutic/adverse effects of Dextromethorphan if Terbinafine is initiated, discontinued or dose changed.
Doxepin	Terbinafine may reduce the metabolism and clearance of Doxepin. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Doxepin is initiated, discontinued or dose changed.
Doxorubicin	Terbinafine may reduce the metabolism and clearance of Doxorubicin. Consider alternate therapy or monitor for therapeutic/adverse effects of Doxorubicin if Terbinafine is initiated, discontinued or dose changed.
doxorubicin TransDrug	Terbinafine may reduce the metabolism and clearance of Doxorubicin. Consider alternate therapy or monitor for therapeutic/adverse effects of Doxorubicin if Terbinafine is initiated, discontinued or dose changed.
Duloxetine	Terbinafine may reduce the metabolism and clearance of Duloxetine. Consider alternate therapy or monitor for therapeutic/adverse effects of Duloxetine if Terbinafine is initiated, discontinued or dose changed.
Dyphylline	Terbinafine increases the effect and toxicity of theophylline
Flecainide	Terbinafine may reduce the metabolism and clearance of Flecainide. Consider alternate therapy or monitor for therapeutic/adverse effects of Flecainide if Terbinafine is initiated, discontinued or dose changed.
Fluoxetine	Terbinafine may reduce the metabolism and clearance of Fluoxetine. Consider alternate therapy or monitor for therapeutic/adverse effects of Fluoxetine if Terbinafine is initiated, discontinued or dose changed.
Fluphenazine	Terbinafine may reduce the metabolism and clearance of Fluphenazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Fluphenazine if Terbinafine is initiated, discontinued or dose changed.
Fluvoxamine	Terbinafine may reduce the metabolism and clearance of Fluvoxamine. Consider alternate therapy or monitor for therapeutic/adverse effects of Fluvoxamine if Terbinafine is initiated, discontinued or dose changed.
Haloperidol	Terbinafine may reduce the metabolism and clearance of Haloperidol. Consider alternate therapy or monitor for therapeutic/adverse effects of Haloperidol if Terbinafine is initiated, discontinued or dose changed.
Imipramine	Terbinafine may increase the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if terbinafine is initiated, discontinued or dose changed.
Lidocaine	Terbinafine may reduce the metabolism and clearance of Lidocaine. Consider alternate therapy or monitor for therapeutic/adverse effects of Lidocaine if Terbinafine is initiated, discontinued or dose changed.
Lomustine	Terbinafine may reduce the metabolism and clearance of Lomustine. Consider alternate therapy or monitor for therapeutic/adverse effects of Lomustine if Terbinafine is initiated, discontinued or dose changed.
Maprotiline	Terbinafine may reduce the metabolism and clearance of Maprotiline. Consider alternate therapy or monitor for therapeutic/adverse effects of Maprotiline if Terbinafine is initiated, discontinued or dose changed.
Methamphetamine	Terbinafine may reduce the metabolism and clearance of Methamphetamine. Consider alternate therapy or monitor for therapeutic/adverse effects of Methamphetamine if Terbinafine is initiated, discontinued or dose changed.
Metoprolol	Terbinafine may reduce the metabolism and clearance of Metoprolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Metoprolol if Terbinafine is initiated, discontinued or dose changed.
Mexiletine	Terbinafine may reduce the metabolism and clearance of Mexiletine. Consider alternate therapy or monitor for therapeutic/adverse effects of Mexiletine if Terbinafine is initiated, discontinued or dose changed.
Mirtazapine	Terbinafine may reduce the metabolism and clearance of Mirtazapine. Consider alternate therapy or monitor for therapeutic/adverse effects of Mirtazapine if Terbinafine is initiated, discontinued or dose changed.
Moclobemide	Terbinafine may reduce the metabolism and clearance of Moclobemide. Consider alternate therapy or monitor for therapeutic/adverse effects of Moclobemide if Terbinafine is initiated, discontinued or dose changed.
Nefazodone	Terbinafine may reduce the metabolism and clearance of Nefazodone. Consider alternate therapy or monitor for therapeutic/adverse effects of Nefazodone if Terbinafine is initiated, discontinued or dose changed.
Nortriptyline	Terbinafine may increase the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if terbinafine is initiated, discontinued or dose changed.
Oxtriphylline	Terbinafine increases the effect and toxicity of theophylline
Paroxetine	Terbinafine may reduce the metabolism and clearance of Paroxetine. Consider alternate therapy or monitor for therapeutic/adverse effects of Paroxetine if Terbinafine is initiated, discontinued or dose changed.
Perphenazine	Terbinafine may reduce the metabolism and clearance of Perphenazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Perphenazine if Terbinafine is initiated, discontinued or dose changed.
Pipotiazine	Terbinafine may reduce the metabolism and clearance of Pipotiazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Pipotiazine if Terbinafine is initiated, discontinued or dose changed.
Procainamide	Terbinafine may reduce the metabolism and clearance of Procainamide. Consider alternate therapy or monitor for therapeutic/adverse effects of Procainamide if Terbinafine is initiated, discontinued or dose changed.
Promethazine	Terbinafine may reduce the metabolism and clearance of Promethazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Promethazine if Terbinafine is initiated, discontinued or dose changed.
Propafenone	Terbinafine may reduce the metabolism and clearance of Propafenone. Consider alternate therapy or monitor for therapeutic/adverse effects of Propafenone if Terbinafine is initiated, discontinued or dose changed.
Propranolol	Terbinafine may reduce the metabolism and clearance of Propranolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Propranolol if Terbinafine is initiated, discontinued or dose changed.
Protriptyline	Terbinafine may reduce the metabolism and clearance of Protriptyline. Consider alternate therapy or monitor for therapeutic/adverse effects of Protriptyline if Terbinafine is initiated, discontinued or dose changed.
Rifabutin	Rifabutin may increase the metabolism and clearance of Terbinafine. To avoid Terbinafine treatment failure, co-administration should be avoided.
Rifampin	Rifampin may increase the metabolism and clearance of Terbinafine. Co-administration may result in Terbinafine treatment failure.
Rifapentine	Rifapentine may increase the metabolism and clearance of Terbinafine. To avoid Terbinafine treatment failure, co-administration should be avoided.
Risperidone	Terbinafine may reduce the metabolism and clearance of Risperidone. Consider alternate therapy or monitor for therapeutic/adverse effects of Risperidone if Terbinafine is initiated, discontinued or dose changed.
Sertraline	Terbinafine may reduce the metabolism and clearance of Sertraline. Consider alternate therapy or monitor for therapeutic/adverse effects of Sertraline if Terbinafine is initiated, discontinued or dose changed.
Tamoxifen	Terbinafine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
Tamsulosin	Terbinafine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Consider alternate therapy or monitor for changes in therapeutic/adverse effects of Tamsulosin if Terbinafine is initiated, discontinued, or dose changed.
Tetrabenazine	Terbinafine may reduce the metabolism and clearance of Tetrabenazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Tetrabenazine if Terbinafine is initiated, discontinued or dose changed.
Theophylline	Terbinafine increases the effect and toxicity of theophylline
Thioridazine	Terbinafine may increase serum concentrations of Thioridazine. Concomitant therapy is contraindicated.
Timolol	Terbinafine may reduce the metabolism and clearance of Timolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Amytriptyline if Timolol is initiated, discontinued or dose changed.
Tolterodine	Terbinafine may reduce the metabolism and clearance of Tolterodine. Consider alternate therapy or monitor for therapeutic/adverse effects of Tolterodine if Terbinafine is initiated, discontinued or dose changed.
Tramadol	Terbinafine may decrease the effect of Tramadol by decreasing active metabolite production.
Trimipramine	Terbinafine may decrease the metabolism and clearance of Trimipramine. Consider alternate therapy or monitor for changes in Trimipramine efficacy and toxicity if Terbinafine is initiated, discontinued or dose changed. Alteration in Trimipramine dose may be required.
Venlafaxine	Terbinafine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Terbinafine is initiated, discontinued, or dose changed.
Zuclopenthixol	Terbinafine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if terbinafine is initiated, discontinued or dose changed.

食物相互作用

Not Available

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