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F8929

Fluconazole

Name: Fluconazole
Brand: SIGMA

≥98% (HPLC), powder

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₁₃H₁₂F₂N₆O

CAS Number:

86386-73-4

Molecular Weight:

306.27

MDL number:

MFCD00274549

PubChem Substance ID:

24724485

NACRES:

NA.77

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.

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

GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H360D - H362 - H412

Precautionary Statements

P202 - P260 - P263 - P273 - P301 + P312 - P308 + P313

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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Breakpoints for susceptibility testing should not divide wild-type distributions of important target species.

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)

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)

Fluconazole resistance in Candida albicans is induced by Pseudomonas aeruginosa quorum sensing.

H M H N Bandara et al.

Scientific reports, 10(1), 7769-7769 (2020-05-10)

Microorganisms employ quorum sensing (QS) mechanisms to communicate with each other within microbial ecosystems. Emerging evidence suggests that intraspecies and interspecies QS plays an important role in antimicrobial resistance in microbial communities. However, the relationship between interkingdom QS and antimicrobial

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)

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