FLUCONAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H12F2N6O
Molecular Weight	306.2708
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(CN1C=NC=N1)(CN2C=NC=N2)C3=C(F)C=C(F)C=C3

InChI

InChIKey=RFHAOTPXVQNOHP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C13H12F2N6O
Molecular Weight	306.2708
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. It inhibits the fungal lanosterol 14 alpha-demethylase which thereby prevents the formation of ergosterol which is an essential component in the fungal cell membrane. Indicated for the treatment of fungal infections.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28	Inhibitor 8,297		0.127 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginal candidiasis 8	Curative		Approved 8,429	Diflucan
Cryptococcal meningitis 3	Curative		Approved 8,429	Diflucan

C_max

Value	Dose	Analyte	Population
6.72 μg/mL	400 mg single, oral	FLUCONAZOLE plasma	Homo sapiens
2.61 μg/mL	150 mg single, oral	FLUCONAZOLE plasma	Homo sapiens
2.9 μg/mL	2 mg/kg single, oral	FLUCONAZOLE plasma	Homo sapiens
9.8 μg/mL	8 mg/kg single, oral	FLUCONAZOLE plasma	Homo sapiens
5.5 μg/mL	2 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
11.4 μg/mL	4 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
14.1 μg/mL	8 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
1.54 μg/mL	50 mg single, oral	FLUCONAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
156.1 ug*h/mL	150 mg single, oral	FLUCONAZOLE plasma	Homo sapiens
79.5 ug*h/g	150 mg single, oral	FLUCONAZOLE vaginal fluid	Homo sapiens
85.3 ug*h/mL	150 mg single, oral	FLUCONAZOLE vaginal fluid	Homo sapiens
76.4 μg × h/mL	50 mg single, oral	FLUCONAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
30 h	400 mg single, oral	FLUCONAZOLE plasma	Homo sapiens
25 h	2 mg/kg single, oral	FLUCONAZOLE plasma	Homo sapiens
19.5 h	8 mg/kg single, oral	FLUCONAZOLE plasma	Homo sapiens
17.4 h	2 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
15.2 h	4 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
17.6 h	8 mg/kg 1 times / day multiple, intravenous	FLUCONAZOLE plasma	Homo sapiens
46.2 h	50 mg single, oral	FLUCONAZOLE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
88.5%			FLUCONAZOLE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
15 mg/kg 1 times / day steady, oral	unhealthy, 0 - 17 years	Other AEs: Vomiting, Abdominal pain...
5.3 mg/kg 1 times / day steady, oral Recommended	unhealthy, 1 - 12 month	Other AEs: Anaemia, Transaminases increased...
6 mg/kg 1 times / day steady, oral	unhealthy, 1 - 12 month	Disc. AE: Nephrotoxicity, Hepatotoxicity...
400 mg 1 times / day steady, oral Studied dose	unhealthy, 16 - 73 years	Disc. AE: Anemia, Transaminases increased...
400 mg 1 times / day steady, oral Studied dose	unhealthy, 46.1 years	Other AEs: Xerosis, Alopecia...

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AEs

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AE	Significance	Dose	Population
Diarrhea	2.1%	15 mg/kg 1 times / day steady, oral	unhealthy, 0 - 17 years
Nausea	2.3%	15 mg/kg 1 times / day steady, oral	unhealthy, 0 - 17 years
Abdominal pain	2.8%	15 mg/kg 1 times / day steady, oral	unhealthy, 0 - 17 years
Vomiting	5.4%	15 mg/kg 1 times / day steady, oral	unhealthy, 0 - 17 years
Anaemia	1 patient	5.3 mg/kg 1 times / day steady, oral Recommended	unhealthy, 1 - 12 month

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767		inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 P-gp 1,461 UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A7 21 UGT1A8 36 UGT1A9 116 UGT1A10 32 UGT2B7 146 UGT2B15 64 MRP1 106 MRP2 383 MRP3 157 MRP4 204 MRP5 22 BCRP 699 BSEP 402 OATP1B1 788 OATP1B3 706	UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,925	inhibitor 3,277	moderate [IC50 13.1 uM]	yes (co-administration study)
CYP2C9 1,819	inhibitor 3,277	moderate [IC50 30.3 uM]	yes (co-administration study)
BCRP 773	inhibitor 3,277	no
BSEP 403	inhibitor 3,277	no
MRP1 172	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
UGT2B7 389	substrate 3,367	major
UGT1A4 347	substrate 3,367	minor
UGT1A1 418	substrate 3,367	no
UGT1A10 291	substrate 3,367	no
UGT1A3 422	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:46081	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:46081
ChemicalBook	CB3740293	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3740293
ChemicalBook	CB4588407	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4588407
eMolecules	877450	https://www.emolecules.com/cgi-bin/more?vid=877450
MolPort	MolPort-000-883-859	https://www.molport.com/shop/molecule-link/MolPort-000-883-859

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PubMed

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Title	Date	PubMed
In-vitro and in-vivo activities of SCH56592 against Cryptococcus neoformans.	1999 Dec	10590286
In-vitro activity of voriconazole (UK-109,496), LY303366 and other antifungal agents against oral Candida spp. isolates from HIV-infected patients.	1999 Nov	10552989
Long QT syndrome and torsade de pointes in a patient receiving fluconazole.	1999 Nov 16	10577320
Prophylactic fluconazole in liver transplant recipients. A randomized, double-blind, placebo-controlled trial.	1999 Nov 16	10577295
In vitro antifungal activity of BMS-207147 and itraconazole against yeast strains that are non-susceptible to fluconazole.	1999 Oct	10579098

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Patents

Sample Use Guides

In Vivo Use Guide

Dosage and Administration in Adults: Single Dose Vaginal candidiasis: The recommended dosage of DIFLUCAN for vaginal candidiasis is 150 mg as a single oral dose. Multiple Dose SINCE ORAL ABSORPTION IS RAPID AND ALMOST COMPLETE, THE DAILY DOSE OF DIFLUCAN (FLUCONAZOLE) IS THE SAME FOR ORAL (TABLETS AND SUSPENSION) AND INTRAVENOUS ADMINISTRATION. In general, a loading dose of twice the daily dose is recommended on the first day of therapy to result in plasma concentrations close to steady-state by the second day of therapy. Oropharyngeal candidiasis: The recommended dosage of DIFLUCAN for oropharyngeal candidiasis is 200 mg on the first day, followed by 100 mg once daily. Esophageal candidiasis: The recommended dosage of DIFLUCAN for esophageal candidiasis is 200 mg on the first day, followed by 100 mg once daily. Doses up to 400 mg/day may be used.

Route of Administration: Oral

In Vitro Use Guide

Fluconazole inhibited Candida albicans with MIC 0.125-16 ug/ml

Substance Class	Chemical
Record UNII	8VZV102JFY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUCONAZOLE

Official Name

English

1H-1,2,4-TRIAZOLE-1-ETHANOL, 1-(2,4-DIFLUOROPHENYL)-1-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-

Common Name

English

DIFLUCAN

Brand Name

English

FLUCONAZOLI [WHO-IP LATIN]

Common Name

English

BAYT006267

Code

English

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Classification Tree

Code System

Code

Combinations of antibacterials

WHO-ATC

J01RA07

Imidazole and triazole derivatives

WHO-VATC

QD01AC15

Triazole derivatives

WHO-ATC

J02AC01

Heterocyclic Compounds, 1-Ring

NDF-RT

N0000008217

Imidazole and triazole derivatives

WHO-ATC

D01AC15

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Code System

Code

Type

Description

NCI_THESAURUS

C500

PRIMARY

ChEMBL

CHEMBL106

PRIMARY

MERCK INDEX

m5423

PRIMARY

Merck Index

INN

5851

PRIMARY

DRUG CENTRAL

1187

PRIMARY

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Related Record

Type

Details


					8VZV102JFY

FLUCONAZOLE

EXCRETED UNCHANGED

Qualification:

URINE

Amount:

MOLE PERCENT OF AMOUNT ADMINISTERED 80 % (average)


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INHIBITOR

Qualification:

IC50

Amount:

13.1 MICROMOLAR (average)


					8VZV102JFY

FLUCONAZOLE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [99 to 101] WEIGHT PERCENT (limits)


					0M77ZW789J

URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7

INHIBITOR -> METABOLIC ENZYME


					L9DP834D1P

CYTOCHROME P450 2C9

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

MAJOR

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Related Record

Type

Details


					2KH0107L73

FLUCONAZOLE GLUCURONIDE

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

URINE


					3JIJ299EWH

FOSFLUCONAZOLE

PRODRUG -> METABOLITE ACTIVE

Amount:

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Related Record

Type

Details


					9T59BRP61E

ISO FLUCONAZOLE

IMPURITY -> PARENT

Comments:

In the chromatogram obtained with solution (1): ? the area of any peak corresponding to impurity A is not is not greater than 0.8 times the area of the principal peak in the chromatogram obtained with solution (2) (0.4 %).

Amount:

RELATIONSHIP_AMOUNT [<0.4] PERCENT PEAK AREA (limits)


					940ZD7T683

1-BROMO-2-(2,4-DIFLUOROPHENYL)-3-(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL

IMPURITY -> PARENT

Comments:

Fluconazole Impurity H Amount Not Specified.


					7753V1DC29

4-AMINO-1-2-(2,4-DIFLUOROPHENYL)-2-HYDROXY-3(1H-1,2,4-TRIAZOL-1-YL)PROPYL)-4H-1,2,4-TRIAZOLIUM ION

IMPURITY -> PARENT

Comments:

Fluconazole Impurity I Amount Not Specified.


					150GCO461X

1,1'-(1,3-PHENYLENE)DI-1H-1,2,4-TRIAZOLE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.1] PERCENT PEAK AREA (limits)


					616851VAC8

1-(((2RS)-2-(2,4-DIFLUOROPHENYL)OXIRAN-2-YL)METHYL)-1H-1,2,4-TRIAZOLE

IMPURITY -> PARENT

Comments:

Fluconazole Impurity G Amount Not Specified.

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Related Record

Type

Details


					8VZV102JFY

FLUCONAZOLE

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
MAXIMUM TOLERATED DOSE	TOXICITY	400 mg/day (average)

Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED 80 % (average) UNCHANGED	ELDERLY: 22% UNCHANGED EXCRETED AS METABOLITE: 11%

Volume of Distribution	PHARMACOKINETIC	[0.7 to 0.95] Liters/Kilogram (average)

Biological Half-life	PHARMACOKINETIC	30 hours [20 to 50] (average) ADULTS	CHILDREN, AGE 9 MONTHS TO 15 YEARS: 15.2 - 25 HOURS ELDERLY: 46.2 HOURS PREMATURE NEWBORNS, GESTATIONAL AGE 26 - 29 WEEKS: 73.6 HOURS (WITHIN 36 HOURS OF BIRTH), MEAN OF 53.2 HOURS (6 DAYS LATER) AND 46.6 HOURS (12 DAYS LATER)

Biological Half-life	PHARMACOKINETIC	30 hours (average)

Cmax	PHARMACOKINETIC	6.1 MICROMOLAR (average)	Route Oral Dose PHARMACOKINETIC 100 mg (average)

Volume of Distribution	PHARMACOKINETIC	APPROXIMATE THAT OF TOTAL BODY WATER	ROUTE OF ADMINISTRATION: ORAL

Tmax	PHARMACOKINETIC	[1 to 2] hours (average) ORAL	EFFECT OF FOOD: NONE

Volume of Distribution	PHARMACOKINETIC	[0.722 to 1.069] Liters/Kilogram (average) CHILDREN 5 - 15 YEARS	ROUTE OF AMINISTRATION: IV

ORAL BIOAVAILABILITY	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT ADMINISTERED [>90] % (average) ORAL	EFFECT OF FOOD: NONE

PROTEIN BINDING	PHARMACOKINETIC	[11 to 12] % (average)
Cmax	PHARMACOKINETIC	6.72 microgram/mL [4.12 to 8.08] (average)	ROUTE PHARMACOKINETIC ORAL DOSE PHARMACOKINETIC 400 mg (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator