Voriconazole
Identification
- Name
- Voriconazole
- Accession Number
- DB00582
- Description
Voriconazole (Vfend, Pfizer) is a triazole antifungal medication used to treat serious fungal infections. It is used to treat invasive fungal infections that are generally seen in patients who are immunocompromised. These include invasive candidiasis, invasive aspergillosis, and emerging fungal infections.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Voriconazole (DB00582)
- Weight
- Average: 349.3105
Monoisotopic: 349.11504471 - Chemical Formula
- C16H14F3N5O
- Synonyms
- (R-(R*,S*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- (αR,βS)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- VCZ
- Voriconazol
- Voriconazole
- Voriconazolum
- External IDs
- DRG-0301
- UK-109,496
- UK-109496
Pharmacology
- Indication
For the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp.
- Associated Conditions
- Aspergillosis of the Central Nervous System
- Aspergillosis of the Liver
- Candidemia
- Candidiasis
- Coccidioidomycosis
- Endocarditis caused by Aspergillus
- Esophageal Candidiasis
- Fungal meningitis caused by Exserohilum Infection
- Fusarium infection
- Histoplasmosis
- Infections, Fungal
- Invasive Aspergillosis
- Osteomyelitis caused by Aspergillus
- Penicillium marneffei infection
- Peritonitis caused by Aspergillus
- Scedosporium Infection
- Sinusitis aspergillus
- Aspergillus endophthalmitis
- Disseminated Candidiasis
- Refractory Fungal Infections
- Refractory Oral Candidiasis
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Voriconazole is a triazole antifungal agent indicated for use in the treatment of fungal infections including invasive aspergillosis, esophageal candidiasis, and serious fungal infections caused by Scedosporium apiospermum (asexual form of Pseudallescheria boydii) and Fusarium spp. including Fusarium solani. Fungal plasma membranes are similar to mammalian plasma membranes, differing in having the nonpolar sterol ergosterol, rather than cholesterol, as the principal sterol. Membrane sterols such as ergosterol provide structure, modulation of membrane fluidity, and possibly control of some physiologic events. Voriconazole effects the formation of the fungal plasma membrane by indirectly inhibiting the biosynthesis of ergosterol. This results in plasma membrane permeability changes and inhibition of growth.
- Mechanism of action
Voriconazole binds and inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-alpha sterol demethylase. The inhibition of 14-alpha sterol demethylase results in a depletion of ergosterol in fungal cell membrane.
Target Actions Organism ACytochrome P450 51 antagonistinhibitorYeast - Absorption
The oral bioavailability is estimated to be 96% (CV 13%).
- Volume of distribution
The estimated volume of distribution of voriconazole is 4.6 L/kg 9. Population pharmacokinetic studies estimate the median volume of distribution to be 77.6 L with the central compartment estimated at 1.07 L/kg 6
- Protein binding
Voriconazole is 58% bound to plasma proteins 9.
- Metabolism
Hepatic. The major metabolite of voriconazole is the N-oxide, which accounts for 72% of the circulating radiolabelled metabolites in plasma. Since this metabolite has minimal antifungal activity, it does not contribute to the overall efficacy of voriconazole.
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- Route of elimination
Voriconazole is eliminated via hepatic metabolism with less than 2% of the dose excreted unchanged in the urine.
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The minimum lethal oral dose in mice and rats was 300 mg/kg (equivalent to 4 and 7 times the recommended maintenance dose (RMD), based on body surface area). At this dose, clinical signs observed in both mice and rats included salivation, mydriasis, titubation (loss of balance while moving), depressed behavior, prostration, partially closed eyes, and dyspnea. Other signs in mice were convulsions, corneal opacification and swollen abdomen.
- Affected organisms
- Yeast and other fungi
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYPC19*17 (T;T) / (C;T) C > T Effect Directly Studied Patients with this genotype in CYP2C19 are ultra fast metabolizers and require higer doses of voriconazole to attain the therapeutic effect. Details Cytochrome P450 2C19 CYP2C19*2 Not Available 681G>A Directly Studied Effect The presence of this polymorphism in CYP2C19 is associated with poor metabolism of voriconazole. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Directly Studied Effect The presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of voriconazole. Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G ADR Inferred Poor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disorders Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Voriconazole can be increased when it is combined with Abametapir. Abatacept The metabolism of Voriconazole can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Voriconazole. Abiraterone The metabolism of Voriconazole can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Voriconazole. Acebutolol The risk or severity of QTc prolongation can be increased when Voriconazole is combined with Acebutolol. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Voriconazole. Acetohexamide The serum concentration of Acetohexamide can be increased when it is combined with Voriconazole. Acetyl sulfisoxazole The metabolism of Voriconazole can be decreased when combined with Acetyl sulfisoxazole. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Voriconazole. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take separate from meals. Take voriconazole at least one hour before or after eating for optimal absorption.
Products
- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataVfend Tablet 200 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU 
Vfend Tablet 50 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet 200 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet 50 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet 200 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet 50 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet, film coated 50 mg/1 Oral Cardinal Health 2002-05-24 2012-01-31 US 
Vfend Powder, for suspension 40 mg/ml Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet 50 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Powder, for suspension 40 mg/1mL Oral Roerig 2003-03-28 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAch-voriconazole Tablet Oral Accord Healthcare Inc Not applicable Not applicable Canada 
Ach-voriconazole Tablet Oral Accord Healthcare Inc Not applicable Not applicable Canada Apo-voriconazole Tablet Oral Apotex Corporation 2014-04-14 Not applicable Canada Apo-voriconazole Tablet Oral Apotex Corporation 2014-04-14 Not applicable Canada Auro-voriconazole Tablet Oral Auro Pharma Inc Not applicable Not applicable Canada Auro-voriconazole Tablet Oral Auro Pharma Inc Not applicable Not applicable Canada Med-voriconazole Tablet Oral Generic Medical Partners Inc Not applicable Not applicable Canada Mylan-voriconazole Tablet Oral Mylan Pharmaceuticals Not applicable Not applicable Canada Mylan-voriconazole Tablet Oral Mylan Pharmaceuticals Not applicable Not applicable Canada PMS-voriconazole Powder, for solution Intravenous Pharmascience Inc Not applicable Not applicable Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- J02AC03 — Voriconazole
- Drug Categories
- 14-alpha Demethylase Inhibitors
- Anti-Infective Agents
- Antifungal Agents
- Antiinfectives for Systemic Use
- Antimycotics for Systemic Use
- Azole Antifungals
- Chemically-Induced Disorders
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (moderate)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Inhibitors (strong)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strong)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strong)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Photosensitizing Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Steroid Synthesis Inhibitors
- Triazole Derivatives
- Triazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Halopyrimidines / Fluorobenzenes / Aryl fluorides / Triazoles / Tertiary alcohols / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides show 2 more
- Substituents
- 1,2,4-triazole / Alcohol / Aromatic alcohol / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Fluorobenzene / Halobenzene show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary alcohol, triazole antifungal drug, conazole antifungal drug, pyrimidines, difluorobenzene (CHEBI:10023)
Chemical Identifiers
- UNII
- JFU09I87TR
- CAS number
- 137234-62-9
- InChI Key
- BCEHBSKCWLPMDN-MGPLVRAMSA-N
- InChI
- 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
- IUPAC Name
- (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
- SMILES
- C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1
References
- Synthesis Reference
Venkataraman Sundaram, Venkata Bhaskara Rao Uppala, Surya Prabhakar Akundi, Venkateswarlu Muvva, Vijayawardhan Chitta, Alekhya Donthula, Manoj Ramesh Kharkar, Surya Narayana Devarakonda, Subba Reddy Peddireddy, "Process For Preparing Voriconazole." U.S. Patent US20080194820, issued August 14, 2008.
US20080194820- General References
- Herbrecht R, Denning DW, Patterson TF, Bennett JE, Greene RE, Oestmann JW, Kern WV, Marr KA, Ribaud P, Lortholary O, Sylvester R, Rubin RH, Wingard JR, Stark P, Durand C, Caillot D, Thiel E, Chandrasekar PH, Hodges MR, Schlamm HT, Troke PF, de Pauw B: Voriconazole versus amphotericin B for primary therapy of invasive aspergillosis. N Engl J Med. 2002 Aug 8;347(6):408-15. [PubMed:12167683]
- Patterson TF, Boucher HW, Herbrecht R, Denning DW, Lortholary O, Ribaud P, Rubin RH, Wingard JR, DePauw B, Schlamm HT, Troke P, Bennett JE: Strategy of following voriconazole versus amphotericin B therapy with other licensed antifungal therapy for primary treatment of invasive aspergillosis: impact of other therapies on outcome. Clin Infect Dis. 2005 Nov 15;41(10):1448-52. Epub 2005 Oct 13. [PubMed:16231256]
- Kullberg BJ, Sobel JD, Ruhnke M, Pappas PG, Viscoli C, Rex JH, Cleary JD, Rubinstein E, Church LW, Brown JM, Schlamm HT, Oborska IT, Hilton F, Hodges MR: Voriconazole versus a regimen of amphotericin B followed by fluconazole for candidaemia in non-neutropenic patients: a randomised non-inferiority trial. Lancet. 2005 Oct 22-28;366(9495):1435-42. [PubMed:16243088]
- Ally R, Schurmann D, Kreisel W, Carosi G, Aguirrebengoa K, Dupont B, Hodges M, Troke P, Romero AJ: A randomized, double-blind, double-dummy, multicenter trial of voriconazole and fluconazole in the treatment of esophageal candidiasis in immunocompromised patients. Clin Infect Dis. 2001 Nov 1;33(9):1447-54. Epub 2001 Sep 26. [PubMed:11577374]
- Walsh TJ, Pappas P, Winston DJ, Lazarus HM, Petersen F, Raffalli J, Yanovich S, Stiff P, Greenberg R, Donowitz G, Schuster M, Reboli A, Wingard J, Arndt C, Reinhardt J, Hadley S, Finberg R, Laverdiere M, Perfect J, Garber G, Fioritoni G, Anaissie E, Lee J: Voriconazole compared with liposomal amphotericin B for empirical antifungal therapy in patients with neutropenia and persistent fever. N Engl J Med. 2002 Jan 24;346(4):225-34. [PubMed:11807146]
- Shi C, Xiao Y, Mao Y, Wu J, Lin N: Voriconazole: A Review of Population Pharmacokinetic Analyses. Clin Pharmacokinet. 2019 Jun;58(6):687-703. doi: 10.1007/s40262-019-00735-7. [PubMed:30687893]
- Pfizer Canada: Voriconazole Product Monograph [Link]
- International Patent WO 98/58677: Pharmaceutical formulations containing voriconazole [Link]
- VFENDⓇ FDA Label [Link]
- Health Canada Approved Products: Vfend (voriconazole) multiple forms/routes [Link]
- External Links
- Human Metabolome Database
- HMDB0014720
- KEGG Drug
- D00578
- KEGG Compound
- C07622
- PubChem Compound
- 71616
- PubChem Substance
- 46506421
- ChemSpider
- 64684
- BindingDB
- 50333117
- 121243
- ChEBI
- 10023
- ChEMBL
- CHEMBL638
- ZINC
- ZINC000000014864
- Therapeutic Targets Database
- DAP001271
- PharmGKB
- PA10233
- PDBe Ligand
- VOR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Voriconazole
- AHFS Codes
- 08:14.08 — Azoles
- PDB Entries
- 3mdt / 4uym / 4ze0 / 5hs1 / 6ay6 / 6h1o
- FDA label
- Download (321 KB)
- MSDS
- Download (57.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Aspergillosis / Candidemia 1 4 Completed Not Available Healthy Volunteers 1 4 Completed Basic Science Infections, Fungal 1 4 Completed Diagnostic Drug Drug Interaction (DDI) / Transplantation, Kidney 1 4 Completed Health Services Research Healthy Volunteers 1 4 Completed Prevention Prophylaxis Of Invasive Fungal Infections 1 4 Completed Treatment Antimycotic for Systematic Use 1 4 Completed Treatment Aspergillosis / Candidiasis / Cryptococcosis 1 4 Completed Treatment Candidemia / Candidiasis, Invasive 1 4 Completed Treatment Candidiasis 1
Pharmacoeconomics
- Manufacturers
- Pfizer inc
- Matrix laboratories ltd
- Packagers
- Cardinal Health
- DSM Corp.
- Pfizer Inc.
- Dosage Forms
Form Route Strength Injection Intravenous 200 mg Injection, powder, lyophilized, for solution Oral 200 mg Tablet Oral Injection, solution Intravenous 200 mg Injection, powder, for solution Intravenous 200 mg Powder, for solution Intravenous 200 MG Powder, for suspension Oral 200 mg Powder, for suspension Oral 40 mg/ml Tablet Oral 200 mg Tablet Oral 50 mg Tablet, film coated Oral Tablet, coated Oral 200 mg Powder, for solution Intravenous Injection, powder, for solution Intravenous 10 mg/ml Solution Parenteral 200 mg Injection, powder, lyophilized, for solution 200 mg Injection, powder, for solution Parenteral 200 mg Tablet, film coated Oral 100 MG Powder Intravenous 200 mg Injection, powder, for solution Intravenous 10 mg/1mL Injection, powder, lyophilized, for solution Intravenous 10 mg/1mL Injection, powder, lyophilized, for solution Intravenous 200 mg/1 Powder, for suspension Oral 40 mg/1mL Suspension Oral 40 mg/1mL Tablet Oral 200 mg/1 Tablet Oral 50 mg/1 Tablet, coated Oral 200 mg/1 Tablet, coated Oral 50 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 200 mg Tablet, film coated Oral 50 mg Solution / drops Ophthalmic 1 g/100mL Powder Intravenous Powder, for solution Parenteral 200 MG Powder, for solution 200 MG Tablet, coated Oral 50 mg Injection, powder, lyophilized, for solution Intravenous 200 mg - Prices
Unit description Cost Unit Vfend 40 mg/ml Suspension 75ml Bottle 870.72USD bottle Vfend iv 200 mg vial 143.5USD vial Vfend 200 mg tablet 49.74USD tablet Vfend 50 mg tablet 12.43USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5116844 No 1992-05-26 2009-08-11 US CA2295035 No 2005-04-19 2018-06-02 Canada CA2035314 No 2000-01-18 2011-01-30 Canada US5567817 No 1996-10-22 2016-05-24 US US6632803 No 2003-10-14 2018-06-02 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 134 °C Pfizer Canada Product Monograph water solubility Low Patent WO 98/58677 - Predicted Properties
Property Value Source Water Solubility 0.0978 mg/mL 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 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9047 Caco-2 permeable + 0.7219 P-glycoprotein substrate Substrate 0.591 P-glycoprotein inhibitor I Non-inhibitor 0.6113 P-glycoprotein inhibitor II Non-inhibitor 0.8195 Renal organic cation transporter Non-inhibitor 0.5354 CYP450 2C9 substrate Non-substrate 0.727 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.5792 CYP450 1A2 substrate Non-inhibitor 0.7491 CYP450 2C9 inhibitor Inhibitor 0.5203 CYP450 2D6 inhibitor Non-inhibitor 0.8315 CYP450 2C19 inhibitor Inhibitor 0.5784 CYP450 3A4 inhibitor Non-inhibitor 0.7011 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6649 Ames test Non AMES toxic 0.7019 Carcinogenicity Non-carcinogens 0.776 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3469 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8791 hERG inhibition (predictor II) Non-inhibitor 0.6282
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0fh9-2593000000-630f0453fb0da8e2745d
Targets
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Morales IJ, Vohra PK, Puri V, Kottom TJ, Limper AH, Thomas CF Jr: Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. Am J Respir Cell Mol Biol. 2003 Aug;29(2):232-8. Epub 2003 Feb 26. [PubMed:12606318]
- Sanguinetti M, Posteraro B, Fiori B, Ranno S, Torelli R, Fadda G: Mechanisms of azole resistance in clinical isolates of Candida glabrata collected during a hospital survey of antifungal resistance. Antimicrob Agents Chemother. 2005 Feb;49(2):668-79. [PubMed:15673750]
- Li X, Brown N, Chau AS, Lopez-Ribot JL, Ruesga MT, Quindos G, Mendrick CA, Hare RS, Loebenberg D, DiDomenico B, McNicholas PM: Changes in susceptibility to posaconazole in clinical isolates of Candida albicans. J Antimicrob Chemother. 2004 Jan;53(1):74-80. Epub 2003 Dec 4. [PubMed:14657086]
- Thompson GR 3rd, Lewis JS 2nd: Pharmacology and clinical use of voriconazole. Expert Opin Drug Metab Toxicol. 2010 Jan;6(1):83-94. doi: 10.1517/17425250903463878. [PubMed:19947892]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
- Xu Y, Sheng C, Wang W, Che X, Cao Y, Dong G, Wang S, Ji H, Miao Z, Yao J, Zhang W: Structure-based rational design, synthesis and antifungal activity of oxime-containing azole derivatives. Bioorg Med Chem Lett. 2010 May 1;20(9):2942-5. doi: 10.1016/j.bmcl.2010.03.014. Epub 2010 Mar 7. [PubMed:20362444]
- Xu J, Cao Y, Zhang J, Yu S, Zou Y, Chai X, Wu Q, Zhang D, Jiang Y, Sun Q: Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. Eur J Med Chem. 2011 Jul;46(7):3142-8. doi: 10.1016/j.ejmech.2011.02.042. Epub 2011 Feb 24. [PubMed:21420761]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Nadp binding
- Specific Function
- This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
- Gene Name
- FMO1
- Uniprot ID
- Q01740
- Uniprot Name
- Dimethylaniline monooxygenase [N-oxide-forming] 1
- Molecular Weight
- 60310.285 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Trimethylamine monooxygenase activity
- Specific Function
- Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an impor...
- Gene Name
- FMO3
- Uniprot ID
- P31513
- Uniprot Name
- Dimethylaniline monooxygenase [N-oxide-forming] 3
- Molecular Weight
- 60032.975 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Jeong S, Nguyen PD, Desta Z: Comprehensive in vitro analysis of voriconazole inhibition of eight cytochrome P450 (CYP) enzymes: major effect on CYPs 2B6, 2C9, 2C19, and 3A. Antimicrob Agents Chemother. 2009 Feb;53(2):541-51. doi: 10.1128/AAC.01123-08. Epub 2008 Nov 24. [PubMed:19029318]
- Yamazaki H, Nakamoto M, Shimizu M, Murayama N, Niwa T: Potential impact of cytochrome P450 3A5 in human liver on drug interactions with triazoles. Br J Clin Pharmacol. 2010 Jun;69(6):593-7. doi: 10.1111/j.1365-2125.2010.03656.x. [PubMed:20565450]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Jeong S, Nguyen PD, Desta Z: Comprehensive in vitro analysis of voriconazole inhibition of eight cytochrome P450 (CYP) enzymes: major effect on CYPs 2B6, 2C9, 2C19, and 3A. Antimicrob Agents Chemother. 2009 Feb;53(2):541-51. doi: 10.1128/AAC.01123-08. Epub 2008 Nov 24. [PubMed:19029318]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Hyland R, Jones BC, Smith DA: Identification of the cytochrome P450 enzymes involved in the N-oxidation of voriconazole. Drug Metab Dispos. 2003 May;31(5):540-7. [PubMed:12695341]
- Murayama N, Imai N, Nakane T, Shimizu M, Yamazaki H: Roles of CYP3A4 and CYP2C19 in methyl hydroxylated and N-oxidized metabolite formation from voriconazole, a new anti-fungal agent, in human liver microsomes. Biochem Pharmacol. 2007 Jun 15;73(12):2020-6. doi: 10.1016/j.bcp.2007.03.012. Epub 2007 Mar 19. [PubMed:17433262]
- Jeong S, Nguyen PD, Desta Z: Comprehensive in vitro analysis of voriconazole inhibition of eight cytochrome P450 (CYP) enzymes: major effect on CYPs 2B6, 2C9, 2C19, and 3A. Antimicrob Agents Chemother. 2009 Feb;53(2):541-51. doi: 10.1128/AAC.01123-08. Epub 2008 Nov 24. [PubMed:19029318]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Jeong S, Nguyen PD, Desta Z: Comprehensive in vitro analysis of voriconazole inhibition of eight cytochrome P450 (CYP) enzymes: major effect on CYPs 2B6, 2C9, 2C19, and 3A. Antimicrob Agents Chemother. 2009 Feb;53(2):541-51. doi: 10.1128/AAC.01123-08. Epub 2008 Nov 24. [PubMed:19029318]
- Flockhart Table of Drug Interactions [Link]
- Drug Interactions & Labeling - FDA [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Voriconazole FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Voriconazole FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Flockhart Table of Drug Interactions [Link]
Drug created on June 13, 2005 07:24 / Updated on January 26, 2021 22:45