top of page
Search

Tolnaftate

Chemical Structure / Formula of Tolnaftate

  • Formula: C19H17NOS

  • Structure: A thiocarbamate antifungal with a naphthyl group.


Chemical Structure of Tolnaftate

Mechanism of Action

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

Uses

  • 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


bottom of page