Topical Azoles

The key clinical focus of topical azoles is the treatment of cutaneous and mucosal yeast infections (e.g. Candida spp.), but some agents such as efinaconazole and tioconazole have particular efficacy against dermatophytes while others are active against a range of clinically relevant molds, dimorphic fungi, and bacterial species. All structures are shown in Table 161.1. Table 161.1 Available topical azoles, including chemical name, structure, and chemical formula. https://www.niso.org/standards/z39-96/ns/oasis-exchange/table">

Compound

Structure

Chemical Formula

Bifonazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₂H₁₈N₂

Butoconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_2.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₉H₁₇Cl₃N₂S

Clotrimazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_3.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₂H₁₇ClN₂

Croconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_4.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₅ClN₂O·HCl

Eberconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_5.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₄Cl₂N₂

Econazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_6.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₅Cl₃N₂O

Enilconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_7.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₄H₁₄Cl₂N₂O

Fenticonazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_8.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₄H₂₀Cl₂N₂OS

Flutrimazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_9.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₂H₁₆F₂N₂

Isoconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_10.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₄Cl₄N₂O

Lanoconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_11.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₄H₁₀ClN₃S₂

Neticonazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_12.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₇H₂₂N₂OS

Oxiconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_13.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₃Cl₄N₃O

Sertaconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_14.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₀H₁₅Cl₃N₂OS

Sulconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_15.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₁₅O₃N₂S

Terconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_16.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₂₆H₃₁Cl₂N₅O₃

Tioconazole

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_17.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₆H₁₃O₃N₂OS

Efinaconazole (formerly KP-103)

https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/tab161_18.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>

C₁₈H₂₂F₂N₄O