The Discovery Of Fluconazole, Crystalline Powder, And, An Orally Active Bistriazole Antifungal Agent

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Leighton Wireman PHBS 2901.01 Dr. Christoff 30 March 2016 Fluconazole Background/History Fluconazole is a white, hygroscopic, crystalline powder, and is an orally active bistriazole antifungal agent.1 The discovery of fluconazole was a milestone in the pharmaceutical industry because it was the first antifungal drug that could be used both orally for minor infections, and intravenously for serious systemic infections. The development and use of antifungals continues to become more of a necessity as the need for protecting immunosuppressed and HIV patients from developing fungal infections increases.2 Although fungal thrush was recorded to be a fatal disease as early as the 1600s, the development of antifungals did start until the 1900s…show more content…
These turning points led to the formation of several bis-triazoles. The first was a chloroacetyl derivative, which was reacted with 1,2,4-triazol to yield a ketone, which was then converted to an epoxide and then opened, resulting in the first bis-triazole derivative. The second approach required converting dichloroacetone to dichloropropanol derivative and reacting it with 1,2,4-triazole, which produced the second bis-triazole. These bis-triazoles were then synthesized in a large number of 2-substituted 1,3-bis-triazolylpropan-2-ol derivatives. Out of the tested derivatives, it was found that the 2,4-difluorophenyl analogue was water soluble, meaning it was could be used intravenously; hence the successful development of fluconazole.2 Chemistry Fluconazole, which is a systemic triazole, has a molecular weight of 306.27 g/mol. The drug should be stored in airtight containers at 30°C. The chemical name for fluconazole is 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol, and chemical structure (Figure 1) is: Figure 1. Diflucan [Package Insert]. New York, NY: Pfizer Inc., March 2013. It is soluble in alcohol, toluene, and acetone, and slightly soluble in chloroform, isopropyl alcohol, and water.4 Diflucan- the brand name for flucnonzaole- in oral suspension contains 350 mg or 1400 mg of fluconazole and the

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