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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
Structure of FLUCONAZOLE

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

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:48:37 UTC 2023
Edited
by admin
on Sat Dec 16 17:48:37 UTC 2023
Record UNII
8VZV102JFY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUCONAZOLE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
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
Fluconazole [WHO-DD]
Common Name English
BAYT-006267
Code English
FLUCONAZOLE [MI]
Common Name English
FLUCONAZOLE [USP MONOGRAPH]
Common Name English
FLUCONAZOLE [ORANGE BOOK]
Common Name English
UK-49858
Code English
FLUCONAZOLE [WHO-IP]
Common Name English
NSC-758661
Code English
ZOLTEC
Common Name English
FLUCONAZOLE [USP-RS]
Common Name English
fluconazole [INN]
Common Name English
FLUCONAZOLE [EP MONOGRAPH]
Common Name English
FLUCONAZOLE [HSDB]
Common Name English
FLUCONAZOLE [MART.]
Common Name English
UK-49,858
Code English
DIFLUCONAZOLE
Common Name English
2,4-DIFLUORO-1',1'-BIS(1H-1,2,4-TRIAZOL-1-YLMETHYL)BENZYL ALCOHOL
Common Name English
ALKANAZOLE
Common Name English
FLUCONAZOLE [VANDF]
Common Name English
FLUCONAZOLE [JAN]
Common Name English
FLUCONAZOLE [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC J01RA07
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
WHO-VATC QD01AC15
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
WHO-ATC J02AC01
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
NDF-RT N0000008217
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
WHO-ATC D01AC15
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
NCI_THESAURUS C514
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
WHO-VATC QJ02AC01
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
LIVERTOX NBK548300
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
NDF-RT N0000175487
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.3
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C500
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL106
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
MERCK INDEX
m5423
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY Merck Index
INN
5851
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
DRUG CENTRAL
1187
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
EVMPD
SUB07674MIG
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
NDF-RT
N0000185504
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
HSDB
7420
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
DRUG BANK
DB00196
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
LACTMED
Fluconazole
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
NDF-RT
N0000182141
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
RS_ITEM_NUM
1271700
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
DAILYMED
8VZV102JFY
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
NSC
758661
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
WIKIPEDIA
FLUCONAZOLE
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
CAS
86386-73-4
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
CHEBI
46081
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
NDF-RT
N0000182140
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
RXCUI
4450
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY RxNorm
PUBCHEM
3365
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
SMS_ID
100000092657
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FLUCONAZOLE
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY Description: A white or almost white, crystalline powder.Solubility: Slightly soluble in water, freely soluble in methanol, soluble in acetone.Category: Antifungal.Storage: Fluconazole should be kept in a tightly closed container.Additional information: Fluconazole is hygroscopic and exhibits polymorphism.Definition: Fluconazole contains not less than 99.0% and not more than 101.0% of C13H12F2N6O, calculated with reference to the dried substance.
EPA CompTox
DTXSID3020627
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
FDA UNII
8VZV102JFY
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
MESH
D015725
Created by admin on Sat Dec 16 17:48:40 UTC 2023 , Edited by admin on Sat Dec 16 17:48:40 UTC 2023
PRIMARY
Related Record Type Details
Structure of FLUCONAZOLE
EXCRETED UNCHANGED
URINE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
IC50
Structure of FLUCONAZOLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7
INHIBITOR -> METABOLIC ENZYME
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
MAJOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
IC50
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of FLUCONAZOLE GLUCURONIDE
METABOLITE -> PARENT
MAJOR
URINE
Structure of FOSFLUCONAZOLE
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of ISO FLUCONAZOLE
IMPURITY -> PARENT
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 %).
Structure of 1-BROMO-2-(2,4-DIFLUOROPHENYL)-3-(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL
IMPURITY -> PARENT
Fluconazole Impurity H Amount Not Specified.
Structure of 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
Fluconazole Impurity I Amount Not Specified.
Structure of 1,1'-(1,3-PHENYLENE)DI-1H-1,2,4-TRIAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-(((2RS)-2-(2,4-DIFLUOROPHENYL)OXIRAN-2-YL)METHYL)-1H-1,2,4-TRIAZOLE
IMPURITY -> PARENT
Fluconazole Impurity G Amount Not Specified.
Structure of 1,1'-(1,3-PHENYLENE)DI-1H-1,2,4-TRIAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 1-((6RS)-4,6-DIFLUORO-6-(1H-1,2,4-TRIAZOL-1-YL)CYCLOHEXA-1,4-DIEN-1-YL)ETHANONE
IMPURITY -> PARENT
Fluconazole Impurity E Amount Not Specified.
Structure of 2-(4-FLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ISO FLUCONAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-DEFLUORO-4-(1H-1,2,4-TRIAZOL-1-YL) FLUCONAZOLE
IMPURITY -> PARENT
In the chromatogram obtained with solution (1):? the area of any peak corresponding to impurity B, when multiplied by a correction factor of 1.5, is not greater than 0.3 times the area of the principal peak in the chromatogram obtained with solution (3) (0.3 %).
Structure of 2,4-DIFLUORO-.ALPHA.-(1H-1,2,4-TRIAZOLYL)ACETOPHENONE
IMPURITY -> PARENT
Structure of 4-DEFLUORO-4-(1H-1,2,4-TRIAZOL-1-YL) FLUCONAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(2,4-DIFLUOROPHENYL)-3-(1H-1,2,4-TRIAZOL-1-YL)PROPANE-1,2-DIOL
IMPURITY -> PARENT
Fluconazole Impurity F Amount Not Specified.
Structure of 2-(4-FLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL
IMPURITY -> PARENT
Amount not specified.
Structure of 4-DEFLUORO-4-(1H-1,2,4-TRIAZOL-1-YL) FLUCONAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1,1'-(1,3-PHENYLENE)DI-1H-1,2,4-TRIAZOLE
IMPURITY -> PARENT
The test is not valid, unless in the chromatogram obtained with solution (4), the resolution between the peaks due to impurity C and fluconazole is at least 3.0. In the chromatogram obtained with solution (1):? the area of any peak corresponding to impurity C is not is not greater than 0.1 times the area of the principal peak in the chromatogram obtained with solution (3) (0.1 %).
Related Record Type Details
Structure of FLUCONAZOLE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
MAXIMUM TOLERATED DOSE TOXICITY
Route of Elimination PHARMACOKINETIC ELDERLY: 22% UNCHANGED

EXCRETED AS METABOLITE: 11%

Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC 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
Cmax PHARMACOKINETIC Route

Dose
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

Tmax PHARMACOKINETIC EFFECT OF FOOD: NONE

Volume of Distribution PHARMACOKINETIC ROUTE OF AMINISTRATION: IV

ORAL BIOAVAILABILITY PHARMACOKINETIC EFFECT OF FOOD: NONE

PROTEIN BINDING PHARMACOKINETIC
Cmax PHARMACOKINETIC ROUTE
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
NIH
NCATS
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