Voriconazole (CED0001958)

Record Information

Version

1.0

Creation Date

2016-05-22 05:46:02 UTC

Update Date

2026-08-19 14:39:42 UTC

Accession Number

CHEM019030

Identification

Common Name

Voriconazole

Class

Small Molecule

Description

Voriconazole is an organic compound with the formula C16H14F3N5O and an average molecular weight of 349.31 g/mol. Voriconazole belongs to the phenylpropanes, a subclass of benzene and substituted derivatives within the organic compounds. It functions as a biological drug (PMC6263395) and a biological antifungal agent (PMC6979503). At the molecular level, it acts as an antagonist and an inhibitor of Lanosterol 14-alpha demethylase (ERG11). The compound is used in the treatment of candidiasis (PMC7132439) and headache (PMC1492602). Recorded exposure routes for the substance include oral and intravenous administration. Voriconazole is found in or released from nine recorded sources, including antimycotics within healthcare, pharmaceuticals, and veterinary products. Other sources include floors in building and construction; electrical and electronic equipment such as television systems, antennas, magnets, and sparking plugs; and household cleaning and consumer products including non electric simulated smoking devices, cigar cigarettes, and other smoking requisites.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(AlphaR,betas)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChEBI
(R-(R,s))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChEBI
VCZ	ChEBI
Vfend	ChEBI
Voriconazol	ChEBI
Voriconazolum	ChEBI
(AlphaR,betas)-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(AlphaR,betas)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(R-(R,s))-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(R-(R,s))-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator

Chemical Formula

C₁₆H₁₄F₃N₅O

Average Molecular Mass

349.311 g/mol

Monoisotopic Mass

349.115 g/mol

CAS Registry Number

137234-62-9

IUPAC Name

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Traditional Name

voriconazole

SMILES

C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

InChI Identifier

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

InChI Key

BCEHBSKCWLPMDN-MGPLVRAMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Fluorobenzene
Halobenzene
Halopyrimidine
Aryl halide
Pyrimidine
Aryl fluoride
Heteroaromatic compound
1,2,4-triazole
Tertiary alcohol
Azole
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:10023 )
triazole antifungal drug (CHEBI:10023 )
conazole antifungal drug (CHEBI:10023 )
pyrimidines (CHEBI:10023 )
difluorobenzene (CHEBI:10023 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.098 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	2.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-007o-9870000000-37f0e72d184d58adf95f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00gs-9165100000-2b5d1149e34858faa6bb	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fh9-2593000000-630f0453fb0da8e2745d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ikf-0094000000-e4b4765d05aa953ac516	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00c0-0690000000-54968439d5df7f27f9db	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0039000000-4831581820baa773cbd0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0249000000-d1f4e5629407a5b0f052	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9330000000-8840243a922d085b8d82	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9013000000-c8af89477bf516cdf196	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9014000000-947fc7640f570d4afdd7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-9000000000-912a372757f51f1a9f40	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1009000000-f770d46865506a5b9cc2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9000000000-e0260b8b6ec84bcf2c45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9000000000-cd28fa5bc96d882612d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9006000000-cc33590c7b94ecaefd7f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9031000000-899de365c4e23b31ebf2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9210000000-21d95020c2f323256ddf	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2237.0	Log mg/kg	[1300:4000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
headache	is_treatment_for	Not Available	PMC1492602
candidiasis	is_treatment_for	Not Available	PMC7132439
invasive aspergillosis	is_treatment_for	Not Available	PMC7132439
aspergillosis	is_treatment_for	Not Available	PMC7132439
cryptococcosis	is_treatment_for	Not Available	PMC7132439
fusariosis	is_treatment_for	Not Available	PMC7132439

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
348	Antimycotics	Healthcare, pharmaceuticals & veterinary products	Not Available
497	Floors	Building & Construction	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
533	Sparking Plugs	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
602	Molluscicides	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Voriconazole Action Pathway

Voriconazole Metabolism

Voriconazole Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	23.4326
Click to view 3D structure	Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	49.4343
Click to view 3D structure	Lanosterol 14-alpha demethylase	P10613	Yeast	Predicted (SEA)	0.0778492
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	27.0915
Click to view 3D structure	14-alpha sterol demethylase	Q96W81	Neosartorya fumigata (Aspergillus fumigatus)	Predicted (SEA)	0.0778492
Click to view 3D structure	Sterol 14-alpha demethylase cyp51A	Q4WNT5	Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSCA1100) (Aspergillus fumigatus)	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	B8NUK6	Aspergillus	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	G4WW85	Aspergillus	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q9P8R0	Aspergillus	Predicted (SEA)	0.0778492
Click to view 3D structure	Sterol 14-alpha demethylase	Q7Z1V1	Trypanosoma cruzi (strain CL Brener)	Predicted (SEA)	0.856341
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	14.7135
Click to view 3D structure	Coenzyme A biosynthesis bifunctional protein CoaBC	P9WNZ1	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	0.544945
Click to view 3D structure	Cholesterol 24-hydroxylase	Q9Y6A2	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	UDP-glucuronosyltransferase 1A4	P22310	Humans	Predicted (SEA)	1.24559
Click to view 3D structure	Cytochrome P450 14alpha-demethylase	A1XG20	Penicillium digitatum	Predicted (SEA)	2.17978
Click to view 3D structure	Scytalone dehydratase	P56221	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	Predicted (SEA)	35.1878
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	389.013
Click to view 3D structure	Cytochrome P450 11B2, mitochondrial	P19099	Humans	Predicted (SEA)	233.158
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15538	Humans	Predicted (SEA)	269.67
Click to view 3D structure	Heat shock protein 90 homolog	P46598	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Predicted (SEA)	18.606
Click to view 3D structure	Imidazoleglycerol-phosphate dehydratase	P0CO23	Cryptococcus neoformans var. neoformans B-3501A	Predicted (SEA)	1.63483
Click to view 3D structure	Allene oxide synthase, chloroplastic	Q96242	Arabidopsis thaliana	Predicted (SEA)	23.5883
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	189.407
Click to view 3D structure	Mitogen-activated protein kinase 8	P45983	Humans	Predicted (SEA)	4847.36
Click to view 3D structure	Mitogen-activated protein kinase 9	P45984	Humans	Predicted (SEA)	4777.3
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	5090.25