Terbinafine Hydrochloride
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Terbinafine Hydrochloride ??
- ???
- 204-208°C
- ?? ??
- 15-25°C
- ???
- ???: ???50mg/mL
- ??? ??
- ??
- ??
- ???
- Merck
- 14,9156
- BCS Class
- 1
- InChI
- InChI=1S/C21H25N.ClH/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;1H/b9-5+;
- InChIKey
- BWMISRWJRUSYEX-SZKNIZGXSA-N
- SMILES
- C12C=CC=CC1=CC=CC=2CN(C)C/C=C/C#CC(C)(C)C.Cl
- CAS ??????
- 78628-80-5(CAS DataBase Reference)
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- ?? ? ???? ?? (GHS)
| ??? ?? | Xi,N | ||
|---|---|---|---|
| ?? ???? ?? | 36/37/38-50/53 | ||
| ????? | 26-36/37/39-61-60 | ||
| ????(UN No.) | UN 3077 9/PG 3 | ||
| WGK ?? | 3 | ||
| RTECS ?? | QJ8600100 | ||
| HS ?? | 29214990 | ||
| ?? | LD50 in mice, rats (mg/kg): 4000, 4000 orally; 393, 213 i.v. (Ganzinger) |
Terbinafine Hydrochloride C??? ??, ??, ??
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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.??? ??
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.??
ChEBI: A hydrochloride obtained by reaction of terbinafine with one molar equivalent of hydrogen chloride.Indications
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.?? ??
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.???? ??
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.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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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).Synthesis
Terbinafine is produced from olefin metathesis of 1,3-dichloropropene and neohexene followed by reaction with N-methyl-1-naphthalenemethanamine.Terbinafine Hydrochloride ?? ?? ? ???
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N-??-1-???????? ?????
N-Methyl-1-naphthalenemethanamine
1,3-???????
3.3-???-1-??
(2E)-N,6,6-trimethyl-2-Hepten-4-yn-1-amine
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Terbinafine Hydrochloride ?? ??
???( 975)?? ??
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Terbinafine Hydrochloride ?? ??:
N,N-????????? 3,3-???-1-?? N-??-1-???????? ????? ???? ????? ??? ??? ???? ????? ?? ???? ????????? ????? ???? ???? ???????(??????) ????? ????
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1-Chloro-6,6-dimethyl-2-heptene-4-yne
Topotecan hydrochloride
Meglumine
N-[(2E)-6,6-DiMethyl-2-hepten-4-yn-1-yl]-N,4-diMethyl-1-naphthaleneMethanaMine Hydrochloride