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Merck

F8929

Sigma-Aldrich

Fluconazole

≥98% (HPLC), powder, fungal cytochrome P-450 sterol C-14 α-demethyllation inhibitor

Synonym(s):

2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol

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About This Item

Empirical Formula (Hill Notation):
C13H12F2N6O
CAS Number:
86386-73-4
Molecular Weight:
306.27
MDL number:
MFCD00274549
UNSPSC Code:
12352200
PubChem Substance ID:
24724485
NACRES:
NA.77

Key Documents

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Product Name

Fluconazole, ≥98% (HPLC), powder

Quality Level

100

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: 5 mg/mL

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

room temp

SMILES string

FC1=CC(F)=C(C(CN2N=CN=C2)(O)CN3N=CN=C3)C=C1

InChI

1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2

InChI key

RFHAOTPXVQNOHP-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Fluconazole is used to treat adult neutropenic patients with invasive candidiasis (IC).

Application

Fluconazole has been used to assess minimum inhibitory concentration (MIC)-fungal assay. It has also been used as a positive control in antifungal assay of plants.

Biochem/physiol Actions

Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.
Fluconazole is an antifungal agent; highly selctive inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Potent inhibitor of CYP2C9. Interferes with fungal ergosterol synthesis; downregulates metallothionein gene.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360D,H362,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Lact. - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
036M4709V
124M4737V
102M4731V
111M4736V
060M47071

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Maiken Cavling Arendrup et al.
Antimicrobial agents and chemotherapy, 53(4), 1628-1629 (2009-02-04)
The fluconazole MIC distributions for Candida glabrata from testing 34 different clinical isolates and performing 51 tests on a single isolate mirrored each other. Since what is perceived as biological variation in isolates without resistance mechanisms is mainly methodological variation
Screening of selected medicinal plants for their antifungal properties
Aboh MI, et al.
African Journal of Clinical and Experimental Microbiolog, 20(1), 54-59 (2019)
Synthesis, structures and antimicrobial activity of novel NHC-and Ph3P-Ag (I)-Benzoate derivatives
O Beirne C, et al.
Inorgorganica Chimica Acta, 486, 294-303 (2019)
T Brosh-Nissimov et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 21(11), 1011-1017 (2015-07-18)
Targeting fluconazole therapy to achieve predefined pharmacodynamic goals has been suggested as a means of optimizing the treatment of patients with candidaemia. However, data regarding species-specific dosing targets are inconclusive. We retrospectively analysed a cohort of 75 adult patients with
Current antifungal drugs and immunotherapeutic approaches as promising strategies to treatment of fungal diseases
Nami S, et al.
Biomedicine and Pharmacotherapy, 110, 857-868 (2019)
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