Бутенафин

Substance identification

Butenafine is the free base of the benzylamine class of antifungal agents, N-[[4-(1,1-dimethylethyl)phenyl]methyl]-N-methyl-1-naphthalenemethanamine. Formula C23H27N, CAS 101828-21-1, UNII 91Y494NL0X, DSSTox ID DTXSID7040657. ATC code: D - dermatological preparations.

Basic Attributes

• Molecular Weight: 317.47
• Exact weight: 317.47
• HS code: 2921199090
• PSA Specifications: 3.24000
• XLogP3: 6.77

Physico-chemical characteristics

• Appearance: Solid
• Density: 1.0±0.1 g/cm3
• Melting point: 200–202 °C
• Boiling point: 426.1±14.0 °C at 760 mm Hg. Art.
• Flash point: 187.7±17.0°C
• Refractive index: 1.598
• Solubility in water: 7.56 × 10⁻⁵ g/l

Pharmacological action and application

Butenafine is the only representative of the benzylamine class among antifungal agents, structurally related to allylamines (terbinafine, naftifine), but formally classified as a separate subclass. The mechanism of action is inhibition of squalene epoxidase, an enzyme in the biosynthesis of ergosterol: blockade of the enzyme interrupts the conversion of squalene to squalene oxide, which leads to the accumulation of squalene inside the fungal cell and a simultaneous deficiency of ergosterol, which is necessary for the integrity of the cell membrane. Violation of the membrane increases its permeability, causes leakage of intracellular contents and death of the fungal cell. Extremely low solubility in water (7.56 × 10⁻⁵ g/l) combined with high lipophilicity (XLogP3 6.77) explains the ability of the substance to effectively accumulate in the lipophilic stratum corneum of the skin when applied topically, providing a long-term therapeutic effect at the site of infection.

Scope of application

The active substance of topical antifungal drugs (usually in the form of a hydrochloride salt) for the treatment of dermatophytosis infections of the skin - feet, groin, body. Classified according to the ATC code of group D as a dermatological drug.

The extremely low solubility of the free base in water makes it difficult to directly use it in aqueous dosage forms; therefore, for pharmaceutical production, the base is converted into a more soluble hydrochloride salt, convenient for the preparation of topical creams, solutions and suspensions.

Data completeness

Detailed information on transport codes, GHS classification and parameters of acute toxicity of the free base was not found in open sources (hazard data are given for the hydrochloride salt of the substance); The presented physicochemical indicators are an exhaustive set of available data.

Storage and handling

Store in an airtight container in a dry place at room temperature, protected from light. When working, use gloves and safety glasses.

Form of delivery and transformation into a medicinal product

Butenaphine free base itself is poorly soluble in water (7.56 × 10⁻⁵ g/L), making its direct use in aqueous dosage forms difficult; To obtain a pharmaceutical substance, the base is converted into a hydrochloride salt, which is much more soluble and convenient for the preparation of creams, solutions and suspensions for topical application to the skin.