Terbinafine

SKU: orb1300541

Description

Terbinafine (TDT 067) is a synthetic allylamine antifungal that inhibits squalene epoxidase, disrupting ergosterol synthesis and fungal membrane integrity. It is widely used in vitro and in vivo for researching dermatophyte and yeast infections, serving as a key tool in antifungal mechanism and efficacy studies.

Research Area

Infectious Disease & Virology

Key Properties

• CAS Number: 91161-71-6
• MW: 291.43
• Purity: 99.90%
• Formula: C₂₁H₂₅N
• SMILES: CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=C1C=CC=C2
• Target: Antibiotic,Antibacterial,Antifungal
• Solubility: 10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (6.86 mM);Ethanol:58 mg/mL (199.02 mM);H2O:< 1 mg/mL (insoluble or slightly soluble);DMSO:125 mg/mL (428.92 mM)

Bioactivity

• Target IC50:
  SE:30 nM(Ki)
• In Vivo:
  Terbinafine demonstrates efficacy not only when administered topically but also shows remarkable effectiveness in treating experimental dermatophytoses upon oral administration. In fungal-infected guinea pigs, there is a significant reduction in skin temperature following the fourth dose of terbinafine.
• In Vitro:
  Terbinafine (50 μM to 100 μM) inhibits only marginally the metabolism of ethoxycoumarin (CYP1A2), tolbutamide (CYP2C9), or ethynylestradiol, CsA, and cortisol. Terbinafine proves to be a potent inhibitor of the CYP2D6-mediated dextromethorphan O-demethylation and bufuralol 1-hydroxylation with IC50values of 0.2 μM and 0.25 μM, respectively. Terbinafine is highly activ Aspergillus isolates (minimum inhibitory concentration [MIC] 0.01 to 2 mg/mL) with a primary fungicidal action (minimum fungicidal concentration [MFC] 0.02 to 4 mg/mL). Terbinafine inhibits dextromethorphan O-demethylation with an apparent Ki ranging from 28 to 44 nM in human hepatic microsomes and averaging 22.4 nM for the heterologously expressed enzymes. Terbinafine shows a very strong activity in vitro against Penicillium spp., Paecilomyces spp., Trichoderma spp., Acremonium spp. and Arthrographis spp. with GMs <1 mg/L. Terbinafine decreases the levels of phosphorylated extracellular signal-regulated kinase (ERK). Terbinafine might cause a decrease of MEK, which in turn up-regulates p53 through the inhibition of ERK phosphorylation, and finally causes an increase of p21expression and cell-cycle arrest.

Storage & Handling

• Storage: store at low temperature | Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Candida, Bacterial, bacteria, antibacterial activity, Antibiotic, Lamisil, Fungal, Inhibitor, infections, inhibit, SF 86-327, TDT 067, TDT067, TDT-067, Terbinafine, Terbinex, squalene epoxidase

Compound Identifiers

PubChem CID

1549008