Бутенафина гидрохлорид

Substance identification

Butenafine hydrochloride is the hydrochloride salt of butenafine, an antifungal agent of the benzylamine class. Formula C23H27N·ClH, CAS 101827-46-7, UNII R8XA2029ZI, DSSTox ID DTXSID2048589, NCI Thesaurus Code C47426. Trade names: Mentax, Skorba. Synonym: KP 363.

Basic Attributes

• Molecular weight: 353.92800
• Exact weight: 353.19100
• HS code: 2921499090
• PSA Specifications: 3.24000
• XLogP3: 6.57130

Physico-chemical characteristics

• Appearance: White crystalline powder
• Density: 1.032 g/cm3
• Melting point: 200–202 °C
• Boiling point: 426.1 °C at 760 mm Hg. Art.
• Flash point: 187.7 °C
• Refractive index: 1.598
• Vapor pressure: 1.82 × 10⁻⁷ mm Hg. Art. at 25 °C

Pharmacological action and application

Butenafine is the first and only member of the benzylamine class of antifungals (as opposed to related allylamines such as terbinafine). The mechanism of action is inhibition of squalene epoxidase, a key enzyme in the biosynthesis of ergosterol in the fungal membrane: blockade of the enzyme interrupts the conversion of squalene to squalene oxide, which leads to intracellular accumulation of squalene and simultaneous deficiency of ergosterol. Ergosterol provides structural integrity and fluidity to the fungal cell membrane, similar to cholesterol in human membranes; blocking its synthesis increases the permeability of the membrane, causes leakage of cellular contents and death of the fungal cell. When applied topically, the drug penetrates well into the stratum corneum of the skin, creating therapeutic concentrations at the site of infection without significant systemic absorption. Used to treat superficial skin mycoses (dermatophytosis).

Place among antifungal drugs

Although butenafine is classified as a separate benzylamine subclass, its mechanism of action is identical to the larger class of allylamines (terbinafine, naftifine) - both classes block the same enzyme, squalene epoxidase, in the biosynthesis of ergosterol. Clinically, the drug is used in the form of creams and solutions for mycoses of the feet, inguinal athlete's foot and tinea versicolor, often with a single daily application due to the long-term retention of the substance in the skin.

Safety Information

• Transport codes: NONH for all modes of transport
• Hazard class code: R21
• RTECS number: QJ8585000
• Tags: Xn
• Hazard Statements: H312 - Harmful in contact with skin
• Precautionary statements: P280
• GHS classification: warning H312 (97.56%)

Storage and handling

Store in an airtight container in a dry place at room temperature, protected from light. Use gloves when working, as the substance is harmful in contact with skin.

Place among antifungal drugs

Butenafine is formally classified as a separate benzylamine subclass of antifungal agents, although according to its mechanism of action - inhibition of squalene epoxidase - it is identical to the larger class of allylamines (terbinafine, naftifine). Clinically, butenafine hydrochloride is used in the form of creams and solutions for topical application for dermatophytosis (mycoses of the feet, athlete's foot, tinea versicolor), usually with a single daily application due to the long-term retention of the active substance in the stratum corneum of the skin. The high lipophilicity of the salt (XLogP3 6.57130) in combination with the extremely low vapor pressure (1.82 × 10⁻⁷ mmHg at 25 °C) explains the virtual absence of volatility of the substance during storage and handling of the dry substance.