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Terbinafine HCl

CAS# 78628-80-5

Terbinafine HCl

2D Structure

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Terbinafine HCl

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Chemical Properties of Terbinafine HCl

Cas No. 78628-80-5 SDF Download SDF
PubChem ID 5282481 Appearance Powder
Formula C21H26ClN M.Wt 327.89
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 60 mg/mL (182.99 mM; Need ultrasonic)
Chemical Name (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine;hydrochloride
SMILES [H+].[Cl-].CN(CC=CC#CC(C)(C)C)Cc1cccc2ccccc12
Standard InChIKey BWMISRWJRUSYEX-SZKNIZGXSA-N
Standard 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+;
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Terbinafine HCl

DescriptionSelective TASK3 activator (pEC50 = 6.2). Exhibits >10-fold selectivity for TASK3 over TREK2, TRESK, THIK1 and TASK2. Also inhibits TWIK1 (pIC50 = 5.69). Also antifungal; inhibits fungal sterol biosynthesis by inhibition of squalene epoxidase.

Terbinafine HCl Dilution Calculator

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Preparing Stock Solutions of Terbinafine HCl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0498 mL 15.249 mL 30.498 mL 60.9961 mL 76.2451 mL
5 mM 0.61 mL 3.0498 mL 6.0996 mL 12.1992 mL 15.249 mL
10 mM 0.305 mL 1.5249 mL 3.0498 mL 6.0996 mL 7.6245 mL
50 mM 0.061 mL 0.305 mL 0.61 mL 1.2199 mL 1.5249 mL
100 mM 0.0305 mL 0.1525 mL 0.305 mL 0.61 mL 0.7625 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Terbinafine HCl

Terbinafine hydrochloride is a synthetic allylamine antifungal, which is highly active against dermatophytes, mold, other basic fungi, and some strains of yeast.

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References on Terbinafine HCl

Preparation, characterization, and in vitro permeation study of terbinafine HCl in poloxamer 407-based thermogelling formulation for topical application.[Pubmed:21479748]

AAPS PharmSciTech. 2011 Jun;12(2):496-506.

Upon topical administration, a high penetration rate of antifungal drug into the infected site is desirable to reduce treatment length and systemic side effects which occur especially after a prolonged peroral administration. Thermogelling formulations composed of poloxamer 407, medium chain triglycerides, isopropyl alcohol, dimethyl isosorbide, and water for topical application were developed, and a lipophilic drug Terbinafine HCl (TBF) was incorporated. Previously, a remarkable high permeation rate of a hydrophilic drug 5-aminolevulinic acid from this vehicle was evident compared to different creams from German Pharmacopoeia. By varying the composition of vehicle constituents, a broad range of consistencies and appearances was obtained. Up to 4% TBF could be solubilized in the vehicle. TBF fluxes at steady state across human stratum corneum from these formulations were higher than those from the German Pharmacopoeia Basiscreme Deutscher Arzneimittel Codex and a marketed product at similar concentration of 1%. TBF fluxes increased along with a higher content of TBF in the formulation. The amount of TBF retained in stratum corneum was higher compared to those from both standards of comparison (p < 0.01). The thermodynamic activity of TBF in the thermogelling formulation was lower compared to those in other formulations. Therefore, the nature of the vehicle and its interaction with TBF are suggested to play a significant role in explaining higher fluxes along with higher TBF content. Differential scanning calorimetry measurements revealed comparable T2 and T3 endothermic shifts from all examined formulations suggesting equal influences to the skin lipids.

Formulation, characterization and ex vivo studies of terbinafine HCl liposomes for cutaneous delivery.[Pubmed:24410098]

Curr Drug Deliv. 2014;11(4):521-30.

BACKGROUND: The goal of effective treatment for dermal fungal infections could be highly beneficial by the delivery of antifungal drugs on skin from liposomal application. Topical delivery involves minimizing the flux of the drug through the skin while maximizing its retention on the skin. The aim of the present work was the investigation of the effects of lipids and cholesterol for the development of liposomal formulations as potential carriers for antifungal agent Terbinafine HCl. Phospholipon 90H (hydrogenated phosphatidylcholine) and dimyristoylglycero-3-phosphocholine (DMPC) along with cholesterol were used for preparation of liposomes by ethanol injection method and characterized for drug content, entrapment efficiency, size, zetapotential, vesicle morphology, stability, FTIR, in vitro and ex vivo drug retention studies. RESULTS: Drug entrapment ranged between 39.46+/-0.91% to 70.39+/-0.71%. Vesicles showed good morphological characters with a narrow size distribution, in the size range of 206.9 to 344.8 nm. Gum karaya gel loaded with liposomal dispersion showed prolonged drug retention on the rat skin during ex vivo studies compared to liposomal dispersion and gum karaya plain gel loaded with drug. CONCLUSION: The prolonged retention of drug by the gum karaya gel loaded with liposomal dispersion could effectively exhibit the antifungal activity for prolonged periods for cutaneous delivery.

Iontophoretic terbinafine HCL 1.0% delivery across porcine and human nails.[Pubmed:20012894]

Mycopathologia. 2010 May;169(5):343-9.

BACKGROUND: Onychomycosis is a common disease. Topical treatment is usually not effective due to limitation of trans-nail delivery of antifungal drugs. Successful treatment of deep-seated nail infections remains elusive as the delivery of efficacious levels of antifungal drug to the site of action is very difficult. OBJECTIVES: To evaluate the influence of several parameters including; the effect of low electrical current, incubation time and the presence of electrolyte (NaCl or KCl) on the penetration of terbinafine through the nail plate into the nail bed, using various formulations and concentrations of Terbinafine HCl. METHODS: Iontophoresis was applied across porcine and human nail in vitro to assess its efficiency in enhancing delivery of Terbinafine HCl. RESULTS: In this study, we have demonstrated that an optimal electrolyte concentration (1% NaCl or KCl) is required for an effective delivery. There is a significant increase in drug delivery into the nail and into the receiving compartment in the presence of 3% DMSO. CONCLUSIONS: This study demonstrates the efficacy of iontophoresis in enhancing the trans-nail delivery of terbinafine. Clinical studies are needed to evaluate the feasibility, efficacy and safety of iontophoresis of terbinafine in onychomycosis in human.

Novel topical formulations of Terbinafine-HCl for treatment of onychomycosis.[Pubmed:23295582]

Eur J Pharm Sci. 2013 Mar 12;48(4-5):628-36.

Terbinafine hydrochloride (TBF-HCl) is an active substance that is using for treatment of onychomycosis. Onychomycosis is a fungal infection which is the most common disease of nail plate. The nail plate is a barrier which prevents effective topical treatment of ungual disorders. In this study, TBF-HCl loaded liposome and ethosome formulations and also gel form of these formulations were prepared. The formulations were characterized and in vitro and ex vivo release studies were performed. Nail characterization studies were also performed to examine the effect of formulations and experimental conditions on nail surface. As a result, all formulations can serve as efficient formulations for ungual application of TBF-HCl. By the way, the results of the accumulation studies suggested that liposome poloxamer gel formulation could be promising system for ungual drug delivery due to the better accumulation and easier application of the formulation.

Description

Terbinafine hydrochloride (TDT 067 hydrochloride) is an antifungal medication used to treat fungal infections. It is a potent non-competitive inhibitor of squalene epoxidase from Candida with a Ki of 30 nM. Terbinafine hydrochloride also antibacterial activity against certain Gram-positive and Gram-negative bacteria.

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