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Y0000557

Fluconazole

Name: Fluconazole
Brand: SIAL

European Pharmacopoeia (EP) Reference Standard

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:

41116107

PubChem Substance ID:

329831019

NACRES:

NA.24

grade

pharmaceutical primary standard

API family

fluconazole

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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

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Related Categories

Analytical Reference Standards

Pharmacopeia & Metrological Institute Standards

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Fluconazole EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

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Pricing

1271733

1271722

1271711

PHR1651

PHR1826

PHR1862

PHR2037

Fluconazole Impurity H, Pharmaceutical Secondary Standard; Certified Reference Material

BP1174

Fluconazole, British Pharmacopoeia (BP) Reference Standard

BP1175

Fluconazole impurity standard, British Pharmacopoeia (BP) Reference Standard

PHR2048

Fluconazole Impurity G, Pharmaceutical Secondary Standard; Certified Reference Material

PHR2046

Fluconazole Impurity E, Pharmaceutical Secondary Standard; Certified Reference Material

PHR1900

Fluconazole Impurity A, Pharmaceutical Secondary Standard; Certified Reference Material

PHR9026

1,2,4-Triazole, reference material

PHR9031

2-(2,4-Difluorophenyl)-1,2,3-propanetriol, certified reference material, TraceCERT^®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Pictograms

GHS08,GHS07

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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The impact of routine cryptococcal antigen screening on survival among HIV-infected individuals with advanced immunosuppression in Kenya.

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

Insufficient fluconazole exposure in pediatric cancer patients and the need for therapeutic drug monitoring in critically ill children.

Kim C M van der Elst et al.

Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 59(11), 1527-1533 (2014-08-26)

Fluconazole is recommended as first-line treatment in invasive candidiasis in children and infants. Although timely achievement of adequate exposure of fluconazole improves outcome, therapeutic drug monitoring is currently not recommended. We conducted a retrospective study of critically ill children treated

Wild-type MIC distributions, epidemiological cutoff values and species-specific clinical breakpoints for fluconazole and Candida: time for harmonization of CLSI and EUCAST broth microdilution methods.

M A Pfaller et al.

Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy, 13(6), 180-195 (2010-11-06)

Both the Clinical and Laboratory Standards Institute (CLSI) and the European Committee on Antimicrobial Susceptibility Testing (EUCAST) have MIC clinical breakpoints (CBPs) for fluconazole (FLU) and Candida. EUCAST CBPs are species-specific, and apply only to C. albicans, C. tropicalis and

Pharmacokinetic evaluation of fluconazole in critically ill patients.

Mahipal Sinnollareddy et al.

Expert opinion on drug metabolism & toxicology, 7(11), 1431-1440 (2011-09-03)

Invasive candidiasis has emerged over the last few decades as an increasingly important nosocomial problem for the critically ill, affecting around 2% of intensive care unit patients. Although poor outcomes associated with invasive candidiasis among critically ill patients may relate

Mould-active compared with fluconazole prophylaxis to prevent invasive fungal diseases in cancer patients receiving chemotherapy or haematopoietic stem-cell transplantation: a systematic review and meta-analysis of randomised controlled trials.

M C Ethier et al.

British journal of cancer, 106(10), 1626-1637 (2012-05-10)

Objectives were to compare systemic mould-active vs fluconazole prophylaxis in cancer patients receiving chemotherapy or haematopoietic stem cell transplantation (HSCT). We searched OVID MEDLINE and the Cochrane Central Register of Controlled Trials (1948-August 2011) and EMBASE (1980-August 2011). Randomised controlled

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