Tìm theo
Terbinafine
Các tên gọi khác (4 ) :
  • (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine
  • (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine
  • Terbinafina
  • Terbinafinum
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 91161-71-6
ATC: D01AE15, D01BA02
ĐG : Actavis Group , http://www.actavis.com
CTHH: C21H25N
PTK: 291.4299
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H25N
Phân tử khối
291.4299
Monoisotopic mass
291.198699805
InChI
InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+
InChI Key
InChIKey=DOMXUEMWDBAQBQ-WEVVVXLNSA-N
IUPAC Name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Traditional IUPAC Name
terbinafine
SMILES
CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12
Độ tan chảy
195-198 °C
Độ hòa tan
Slightly soluble
logP
5.9
logS
-5.6
pKa (Strongest Basic)
8.94
PSA
3.24 Å2
Refractivity
98.08 m3·mol-1
Polarizability
35.83 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
1
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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. 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.
Dược Động Học :
▧ Absorption :
Readily absorbed from gastrointestinal tract.
▧ Protein binding :
>99%
▧ Metabolism :
Hepatic
▧ Route of Elimination :
Prior to excretion, terbinafine is extensively metabolized.
▧ Half Life :
36 hours
Chỉ Định : 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).
Tương Tác Thuốc :
  • 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.
  • Rifampicin 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.
Liều Lượng & Cách Dùng : Cream - Topical
Spray - Topical
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Lamasil
  • Công ty :
    Sản phẩm biệt dược : Lamisil
  • Công ty :
    Sản phẩm biệt dược : Terbinex
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00857
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C08079
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02375
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-5710-93
PharmGKB
http://www.pharmgkb.org/drug/PA451614
Wikipedia
http://en.wikipedia.org/wiki/Terbinafine
RxList
http://www.rxlist.com/cgi/generic/terbin.htm
Drugs.com
http://www.drugs.com/cdi/terbinafine.html
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