U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14F3N5O
Molecular Weight 349.3105
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VORICONAZOLE

SMILES

C[C@@H](C1=C(F)C=NC=N1)[C@](O)(CN2C=NC=N2)C3=C(F)C=C(F)C=C3

InChI

InChIKey=BCEHBSKCWLPMDN-MGPLVRAMSA-N
InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1

HIDE SMILES / InChI
Molecular Formula C16H14F3N5O
Molecular Weight 349.3105
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:52:13 UTC 2023
Edited
by admin
on Fri Dec 15 15:52:13 UTC 2023
Record UNII
JFU09I87TR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VORICONAZOLE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
4-PYRIMIDINEETHANOL, A-(2,4-DIFLUOROPHENYL)-5-FLUORO-.BETA.-METHYL-.ALPHA.-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-, (.ALPHA.R,.BETA.S)-
Common Name English
VORICONAZOLE [ORANGE BOOK]
Common Name English
UK-109,496
Code English
voriconazole [INN]
Common Name English
UK-109496
Code English
(.ALPHA.R,.BETA.S)-A-(2,4-DIFLUOROPHENYL)-5-FLUORO-.BETA.-METHYL-.ALPHA.-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-4-PYRIMIDINEETHANOL
Common Name English
VORICONAZOLE [JAN]
Common Name English
VORICONAZOLE [USP-RS]
Common Name English
VFEND
Brand Name English
NSC-759888
Code English
VORICONAZOLE [MART.]
Common Name English
VORICONAZOLE [EMA EPAR]
Common Name English
VORICONAZOLE [MI]
Common Name English
Voriconazole [WHO-DD]
Common Name English
VORICONAZOLE [USAN]
Common Name English
VORICONAZOLE [EP MONOGRAPH]
Common Name English
VORICONAZOLE [USP MONOGRAPH]
Common Name English
VORICONAZOLE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
NDF-RT N0000008217
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
WHO-ATC J02AC03
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
WHO-VATC QJ02AC03
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
NDF-RT N0000175487
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
LIVERTOX NBK547891
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
Code System Code Type Description
RXCUI
121243
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY RxNorm
MESH
C102790
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
DRUG BANK
DB00582
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
NDF-RT
N0000182140
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
USAN
LL-48
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
SMS_ID
100000088018
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
EVMPD
SUB00087MIG
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
CHEBI
10023
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
WIKIPEDIA
Voriconazole
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL638
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
CAS
137234-62-9
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046485
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
MERCK INDEX
m11501
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C1707
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
DAILYMED
JFU09I87TR
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
INN
7269
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
RS_ITEM_NUM
1718008
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
NDF-RT
N0000185504
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
NSC
759888
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
FDA UNII
JFU09I87TR
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
PUBCHEM
71616
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
DRUG CENTRAL
2846
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY
NDF-RT
N0000182141
Created by admin on Fri Dec 15 15:52:13 UTC 2023 , Edited by admin on Fri Dec 15 15:52:13 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
Related Record Type Details
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
IN VITRO
Structure of Voriconazole Camphor Sulfonate
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
Plasma protein binding is estimated to be 58% and was shown to be independent of plasma concentrations achieved following single and multiple oral doses of 200 mg or 300 mg (approximate range: 0.9-15 mg/ml).
BINDING
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
IN VITRO
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
IC50
Structure of VORICONAZOLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Structure of VORICONAZOLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
IN VITRO
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
IC50
Structure of VORICONAZOLE
EXCRETED UNCHANGED
URINE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
IC50
FETAL HEPATIC FLAVIN-CONTAINING MONOOXYGENASE 3 (HUMAN)
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of VORICONAZOLE-5-FLUORO-PYRIMIDIN-4-YL-OXY-GLUCURONIDE
METABOLITE -> PARENT
Structure of VORICONAZOLE N-OXIDE
METABOLITE LESS ACTIVE -> PARENT
MAJOR
PLASMA
Structure of VORICONAZOLE N-OXIDE
METABOLITE LESS ACTIVE -> PARENT
Structure of VORICONAZOLE N-OXIDE
METABOLITE LESS ACTIVE -> PARENT
MAJOR
PLASMA
Structure of VORICONAZOLE-METHYL-O-GLUCORONIDE
METABOLITE -> PARENT
Structure of VORICONAZOLE-GLUCURONIDE
METABOLITE -> PARENT
Related Record Type Details
Structure of 2,4-DIFLUORO-.ALPHA.-(1H-1,2,4-TRIAZOLYL)ACETOPHENONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CAMPHORSULFONIC ACID, (±)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 5-DESFLUORO VORICONAZOLE, (±)-
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.1
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-ETHYL-5-FLUOROPYRIMIDINE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2,4-DIFLUORO-.ALPHA.-(1H-1,2,4-TRIAZOLYL)ACETOPHENONE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CAMPHORSULFONIC ACID, (±)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 5-DESFLUORO VORICONAZOLE, (±)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ENT-VORICONAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of ENT-VORICONAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of VORICONAZOLE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC
Cmax PHARMACOKINETIC Dose

Route

Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC AT STEADY-STATE

Tmax PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966