Fluconazole

Licensed by Pfizer Catalog No.S1331 Synonyms: UK 49858

Fluconazole Chemical Structure

Molecular Weight(MW): 306.27

Fluconazole is a fungal lanosterol 14 alpha-demethylase inhibitor, which thereby prevents the formation of ergosterol,used in the treatment and prevention of superficial and systemic fungal infections.

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Biological Activity

Description Fluconazole is a fungal lanosterol 14 alpha-demethylase inhibitor, which thereby prevents the formation of ergosterol,used in the treatment and prevention of superficial and systemic fungal infections.
Targets
lanosterol 14 alpha-demethylase [1]
In vitro

Fluconazole in combination with amphotericin B (AmB) has a synergistic effect on C. albicans planktonic cells but does not alter AmB activity against biofilms. Fluconazole and caspofungin have an antagonistic effect against biofilms but not with planktonic cells. Fluconazole-mediated membrane perturbation (due to inhibition of ergosterol biosynthesis) increases calcineurin inhibitor intracellular concentrations. Fluconazole treatment significantly reduces levels of ergosterol within the cell in C. albicans planktonic cells, leading to cell membrane perturbation. [1] Fluconazole activity is less sensitive to acidic medium than is that of ketoconazole. Fluconazole is approximately 16-fold less active than ketoconazole against 35 representative isolates of C. albicans at physiologic pH. [2] Fluvastatin, a cholesterol-lowering drug, exhibits minimal activity (MICs of 64 to >128 mg/mL) against Candida species and Cryptococcus neoformans. Fluconazole combined with itraconazole exhibits potent activities against C. albicans, C. tropicalis, C. parapsilosis, and C. neoformans, including flucon- azole-resistant strains of C. albicans and C. tropicalis. [3]

In vivo Fluconazole is very effective in prolonging survival of rats infected with a representative candidal strain. [3] Fluconazole has a dramatic effect on the fungicidal activity of flucytosine in murine cryptococcal meningitis. Fluconazole combined with flucytosine and amphotericin B have significantly improved activity against cryptococcal meningitis compared with the activity of each drug used alone. [4]

Protocol

Solubility (25°C)

In vitro DMSO 61 mg/mL (199.17 mM)
Ethanol 61 mg/mL (199.17 mM)
Water Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
2% DMSO+30% PEG 300+2% Tween 80+ddH2O
For best results, use promptly after mixing.
12mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 306.27
Formula

C13H12F2N6O

CAS No. 86386-73-4
Storage powder
in solvent
Synonyms UK 49858

Bio Calculators

Molarity Calculator

Molarity Calculator

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Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Molarity Calculator

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT02733432 Completed Candidiasis Vulvovaginal|Mycoses|Yeast Infection|Moniliasis Vulvovaginal|Vaginitis Monilial Cidara Therapeutics Inc. June 8 2016 Phase 2
NCT03451110 Completed Healthy Subjects Eisai Inc.|Purdue Pharma LP February 5 2018 Phase 1
NCT01806623 Completed Vulvovaginal Candidiasis Pfizer March 5 2013 Phase 3
NCT01307579 Completed Acute Myeloid Leukemia|Adult Acute Megakaryoblastic Leukemia|Adult Acute Monoblastic Leukemia|Adult Acute Monocytic Leukemia|Adult Acute Myeloid Leukemia in Remission|Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11|Adult Acute Myeloid Leukemia With Maturation|Adult Acute Myeloid Leukemia With Minimal Differentiation|Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11|Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1|Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A|Adult Acute Myeloid Leukemia Without Maturation|Adult Acute Myelomonocytic Leukemia|Adult Erythroleukemia|Adult Pure Erythroid Leukemia|Alkylating Agent-Related Acute Myeloid Leukemia|Childhood Acute Erythroid Leukemia|Childhood Acute Megakaryoblastic Leukemia|Childhood Acute Monoblastic Leukemia|Childhood Acute Monocytic Leukemia|Childhood Acute Myeloid Leukemia in Remission|Childhood Acute Myeloid Leukemia With Maturation|Childhood Acute Myeloid Leukemia With Minimal Differentiation|Childhood Acute Myeloid Leukemia Without Maturation|Childhood Acute Myelomonocytic Leukemia|Fungal Infection|Myeloid Neoplasm|Neutropenia|Recurrent Adult Acute Myeloid Leukemia|Recurrent Childhood Acute Myeloid Leukemia|Secondary Acute Myeloid Leukemia|Untreated Adult Acute Myeloid Leukemia|Untreated Childhood Myeloid Neoplasm Children''s Oncology Group|National Cancer Institute (NCI) April 4 2011 Phase 3
NCT02663674 Suspended Coccidioidomycosis National Institute of Allergy and Infectious Diseases (NIAID) December 29 2015 Phase 4
NCT03028103 Recruiting Diffuse Large B Cell Lymphoma|Primary Mediastinal Lymphoma|Mantle Cell Lymphoma|Advanced Solid Tumor|Marginal Zone Lymphoma Epizyme Inc. March 27 2017 Phase 1

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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P450 (e.g. CYP17) Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID