Difference Between Fluconazole and Itraconazole

The key difference between Fluconazole and Itraconazole is that though both are antifungal medications, fluconazole is not active against Aspergillus whereas Itraconazole is active against Aspergillus. Therefore, itraconazole has a broad range of activity than fluconazole.

The trade name of fluconazole is Diflucan, and the trade name of itraconazole is Sporanox.

CONTENTS

1. Overview and Key Difference
2. What is Fluconazole
3. What is Itraconazole
4. Side by Side Comparison – Fluconazole vs Itraconazole in Tabular Form
5. Summary

What is Fluconazole?

Fluconazole is an antifungal medication for treating fungal infections including candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and pityriasis versicolor. The chemical formula of fluconazole is C₁₃H₁₂F₂N₆O, and the molar mass is 306.27 g/mol. The melting point is around 138-140°C.

Figure 01: The Skeletal Structure of Fluconazole

Fluconazole falls into the class of azoles, which are antifungals. However, it is different from other azole antifungals by the presence of a triazole ring instead of an imidazole ring (as in other azoles). In addition, fluconazole is for the oral use (unlike imidazole antifungals). Fluconazole works best against Candida species, some dimorphic fungi, and dermatophytes.

Side Effects:

Common side effects of fluconazole include rashes, headache, dizziness, nausea, diarrhoea, etc. Some rare side effects include oliguria, seizures, alopecia, liver failure, etc. There are very rare adverse effects as well. Ex: prolonged QT interval.

What is Itraconazole?

Itraconazole is an antifungal medication to treat fungal infections such as aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis. The routes of administration are oral or IV (intravenously). Specifically, this medication is useful in treating Aspergillus infections. Moreover, recent studies have shown that this medicine has anticancer properties as well.

The chemical formula of Itraconazole is C₃₅H₃₈Cl₂N₈O₄, and the molar mass is 705.24 g/mol. It has a very complicated chemical structure. This compound shows chirality; thus exist as a racemic mixture. The melting point of Itraconazole is 170°C.

Figure 02: The Chemical Structure of Itraconazole

Side Effects:

The common side effects of Itraconazole include nausea, vomiting, diarrhoea, rash, and headache. There are some rare side effects as well; such side effects include elevated alanine aminotransferase levels, congestive heart failure, liver failure, etc.

What is the Difference Between Fluconazole and Itraconazole?

Summary – Fluconazole vs Itraconazole

Fluconazole and Itraconazole are two important antifungal medications. The key difference between fluconazole and Itraconazole is that the fluconazole is not active against Aspergillus whereas itraconazole is active against Aspergillus.

Reference:

1. “Itraconazole-A Very Low Bioavailability BCS Class II Drug Case Study.” DisperSol Technologies. Available here 
2. “Fluconazole.” Fluconazole | C13H12F2N6O | ChemSpider. Available here
3. “Fluconazole.” Wikipedia, Wikimedia Foundation, 30 Apr. 2018. Available here 

Image Courtesy:

1.’Fluconazole skeletal formula’By Vaccinationist – PubChem, (Public Domain) via Commons Wikimedia
2.’Itraconazole’By Shaddack – Own work using: ChemWindow, (Public Domain) via Commons Wikimedia 

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