Tolnaftate

Chemical Structure / Formula of Tolnaftate

  • Formula: C₁₉H₁₇NOS
  • Structure: A thiocarbamate antifungal with a naphthyl group.

Tolnaftate

Mechanism of Action

  • Inhibits squalene epoxidase, preventing ergosterol synthesis and causing toxic squalene accumulation in fungal cells.

Uses of Tolnaftate

  • Topical antifungal (tinea infections, athlete’s foot, jock itch, ringworm).

Side Effects

  • Mild skin irritation, dryness, redness.

Structure-Activity Relationship (SAR) of Tolnaftate

Structural Feature SAR Insight
Naphthyl ring Lipophilic moiety essential for activity; mimics fungal squalene epoxidase substrate.
Thiocarbamate group Essential for antifungal action by inhibiting squalene epoxidase, blocking ergosterol synthesis.
Tert-butyl group Enhances potency by increasing membrane penetration.
Rigid structure Important for mimicking the enzyme’s natural substrate.

Synthesis of Tolnaftate

Synthesis of Tolnaftate

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