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T8826

Sigma-Aldrich

Terbinafine hydrochloride

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Synonym(s):
trans-N-(6,6-Dimethyl-2-hepten-4-ylyl)-N-methyl-1-naphthylmethylamine hydrochloride
Empirical Formula (Hill Notation):
C21H25N · HCl
CAS Number:
78628-80-5
Molecular Weight:
327.89
MDL number:
MFCD00145430
PubChem Substance ID:
329826887
NACRES:
NA.85

biological source

synthetic

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

white

solubility

methanol: soluble 50 mg/mL

antibiotic activity spectrum

fungi
yeast

Mode of action

enzyme | inhibits

SMILES string

Cl[H].[H]\C(CN(C)Cc1cccc2ccccc12)=C(\[H])C#CC(C)(C)C

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+;

InChI key

BWMISRWJRUSYEX-SZKNIZGXSA-N

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General description

Allylamine derivative.

Application

Terbinafine hydrochloride is a synthetic allylamine antifungal. It is used to treat dermatophyte infections of the toenail/fingernail, ringworm and jock itch. It is used in adsorption, partition and stability studies.

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.
Terbinafine inhibits squalene monooxygenase thereby blocking the biosynthesis of ergosterol, which is an essential component of fungal cell membranes. The inhibition of squalene monooxygenase also results in the accumulation of squalene. Terbinafine hydrochloride is highly lipophilic and tends to accumulate in skin, nails, and fatty tissues. It is antifungal and antimycotic. It is fungicidal against dermatopytes and some yeasts and is fungistatic against Candida albicans.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Disclaimer

The product is not intendedfor use as a biocide under global biocide regulations, including but notlimited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, EuropeanBiocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’sBiocidal Products Regulation, Korea’s Consumer Chemical Products and BiocideSafety Management Act (K-BPR) and others.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315 - H319 - H335 - H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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James B Y H Behrendorff et al.
Physiologia plantarum, 169(4), 586-599 (2020-02-26)
Stable genetic transformation of plants is a low-efficiency process, and identification of positive transformants usually relies on screening for expression of a co-transformed marker gene. Often this involves germinating seeds on solid media containing a selection reagent. Germination on solid
J Oremusová et al.
Die Pharmazie, 62(4), 273-277 (2007-05-09)
In this study the adsorption, partition and releasing balances of terbinafine hydrochloride have been studied. The adsorption isotherms of antifugal drug terbinafine hydrochloride (terbinafine), on the base of its adsorption from aqueous solutions on the surface of activated charcoal, were
Abdul-Rehman Phull et al.
Medicinal chemistry (Shariqah (United Arab Emirates)), 16(4), 495-506 (2019-11-13)
Silver nanoparticles synthesized by the bio-green method have been applied to various biomedical applications. These procedures are simple, eco-friendly and serve as an alternative to complex chemical methods for the preparation of nanomaterials. In the present study, phytosynthesis of silver
S M Abdel-Rahman et al.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists, 56(3), 243-245 (1999-02-25)
The stability of terbinafine 25 mg/mL (as the hydrochloride salt) in an extemporaneously prepared oral suspension at 25 and 4 degrees C was studied. Twenty 250-mg terbinafine tablets were crushed to a fine powder and diluted to a concentration of
Akira Kotani et al.
Journal of chromatography. A, 1621, 461077-461077 (2020-04-28)
A previous paper of this series of study put forward a basic model of an automated system for predicting detection limits and showed its application to a simple example of isocratic high-performance liquid chromatography (HPLC). This paper describes an expansion
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