Imidazoles

Imidazoles is a large class of medications used for the treatment of fungal infections. Similar to triazoles but differing in chemical structure, Imidazoles work by inhibiting the C-14 α-demethylase enzyme, which is used in the synthesis of lanosterol and ergosterol. Lanosterol and ergosterol are critical to the structure of the fungal membrane. Efflux pumps and alterations in the C-14 α-demethylase enzyme are resistance mechanisms. Most formulations are used for topical infections. Ketoconazole has been used for systemic infections; however, triazoles have a better side effect profile, which limits ketoconazole's systemic use.

Class Drugs

Butoconazole

Clotrimazole

Econazole

Ketoconazole

Miconazole

Oxiconazole

Sertaconazole

Sulconazole

Terconazole

Tioconazole

Class Mechanism of Action

Inhibits C-14 α-demethylase, which is used in the synthesis of lanosterol and ergosterol. Lanosterol and ergosterol are critical to the structure of the fungal membrane

Class Applications

Tinea (cruris, capitis, pedis)

Oral and vulvovaginal candidiasis

Class Adverse Effects

Resistance

• Efflux pumps

• Mutations of C-14 α-demethylase gene, resulting in decreased affinity

Rash

Drug Table

Drug Name	Application	Comments	Image
Butoconazole			"Button" "Cone" "Asshole"
Clotrimazole			"Clover" "Trim" "Asshole"
Econazole			"Economics Book"  "Asshole"
Ketoconazole		Oral Formulation; Adverse Effects; -Hair Loss, oligospermia, gynecomastia; -Nausea/Vomiting; -Headache; -Paresthesia; -Elevation in liver enzymes; Contraindicated in pregnancy and breastfeeding; Inhibits CYP450	"Keto Diet" "Cone" "Asshole"
Miconazole			"Microphone" "Cone" "Asshole"
Oxiconazole			"Oxygen" "Cone" "Asshole"
Sertaconazole			"Serta Mattress" "Cone" "Asshole"
Sulconazole			"Sully" "Cone" "Asshole"
Terconazole			"Terra Cotta" "Cone" "Asshole"
Tioconazole			"Tea" "Cone" "Asshole"