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外観
白色～ほとんど白色粉末～結晶
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用途
スクアレンエポキシダーゼの
選択的阻害作用を示します。
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用途
スクアレンエポキシダーゼ選
択的阻害作用を示します。
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効能
抗真菌薬, エルゴステロール合成阻害薬
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商品名
テルビナフィン (岩城製薬); テルビナフィン塩酸塩 (岩城製薬); ラミシール (サンファーマ); ラミシール (サンファーマ); ラミシール (サンファーマ); ラミシール (サンファーマ)
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説明
Terbinafine hydrochloride is the first orally active allylamine antifungal with 30-fold
greater antifungal activity than naftifine. The compound is indicated for the treatment
of ringworm and fungal nail infections. Terbinatine hydrochloride acts on a single
fungal enzyme, squalene epoxidase, interfering with the biosynthesis of ergosterols in
cell membranes. Unlike other antifungal agents, it does not inhibit cytochrome P450
enzymes.
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化学的特性
Terbinafine hydrochloride is an off-white crystalline material that is soluble in polar organic solventssuch as methanol, ethanol, and methylene chloride but isonly slightly soluble in water. The highly lipophilic freebase is insoluble in water.
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定義
ChEBI: A hydrochloride obtained by reaction of terbinafine with one molar equivalent of hydrogen chloride.
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適応症
Terbinafine Hydrochloride is a synthetic allylamine antifungal
agent, structurally related to naftifine. It inhibits fungal sterol biosynthesis
by inhibiting the enzyme squalene 2,3-epoxidase. The deficiency of
ergosterol and concomitant accumulation of squalene within the fungal
cell results in cell death. It can be fungicidal or fungistatic, depending on
the concentration used, and is effective against dermatophytes, Aspergillus,
blastomycosis, and histoplasmosis. It is only minimally effective against
Candida.
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一般的な説明
Terbinafine Hydrochloride is a synthetic allylamine derivative structurally related to naftifine, antifungal Terbinafine Hydrochloride blocks ergosterol biosynthesis by inhibition of squalene epoxidase, part of the sterol synthesis pathway for the fungal cell membrane.
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生物活性
Terbinafine is a broad-spectrum antifungal agent that has activity against T. rubrum, T. metagrophytes, T. verrucosum, E. floccosum, M. canis, A. fumigatus, and S. schenckii (MIC50s = 0.003-0.8 μg/ml). It selectively inhibits C. albicans squalene epoxidase over rat liver epoxidase (IC50s = 0.03 and 77 μM, respectively). Terbinafine (90-120 μM) induces cell cycle arrest at the G0/G1 phase in COLO 205 tumor cells and human umbilical vein endothelial cells (HUVECs). Formulations containing terbinafine have been used in the treatment of nail and skin fungal infections.
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Biochem/physiol Actions
Mode of Action: Inhibits squalene epoxidase, preventing biosynthesis of ergosterol.
Antimicrobial spectrum: Antifungal and antimycotic. Fungicidal against dermatopytes and some yeasts; fungistatic against Candida albicans.
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副作用
Adverse reactions include lens and retinal disturbances (red/green visual
perception), metallic taste disturbance that may last up to 4 weeks after
medication discontinuation, hepatoxicity, and pancytopenia. Five percent of
patients will experience delayed gastric emptying with symptoms of nausea,
fullness, and/or dyspepsia. Terbinafine does not appear to have any effect on
the cytochrome P-450 systems (Check baseline CBC and LFTs; repeat if taken
for >6 weeks).
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合成
Terbinafine is produced from olefin metathesis of 1,3-dichloropropene and neohexene followed by reaction with N-methyl-1-naphthalenemethanamine.
