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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

product name

Fluconazole, ≥98% (HPLC), powder

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.

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
A-C L Meyer et al.
Tropical medicine & international health : TM & IH, 18(4), 495-503 (2013-02-02)
To test the hypothesis that a screening and treatment intervention for early cryptococcal infection would improve survival among HIV-infected individuals with low CD4 cell counts. Newly enrolled patients at Family AIDS Care and Education Services (FACES) in Kenya with CD4 ≤ 100
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