Identification
- Summary
Voriconazole is a triazole compound used to treat fungal infections.
- Brand Names
- Vfend
- Generic Name
- Voriconazole
- DrugBank Accession Number
- DB00582
- Background
Voriconazole (Vfend, Pfizer) is a triazole antifungal medication used to treat serious fungal infections.14 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. The increased affinity of voriconazole for 14-alpha sterol demethylase makes it useful against some fluconazole-resistant organisms.11
Voriconazole was approved by the FDA under the trade name Vfend on May 24, 2002.15
- 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, cadidemia, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp.13,14
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Aspergillosis of the central nervous system ••• ••••• Treatment of Aspergillosis of the liver ••• ••••• Treatment of Candidemia •••••••••••• •••••• ••••••••• ••••••••• Treatment of Candidemia •••••••••••• •••••• ••••••••• ••••••••••• •••••• Treatment of Candidiasis ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Voriconazole is a fungistatic triazole antifungal used to treat infections by inhibiting fungal growth.13 It is known to cause hepatotoxic and photosensitivity reactions in some patients.
- Mechanism of action
Voriconazole is used to treat fungal infections caused by a variety of organisms but including Aspergillus spp. and Candida spp. Voriconazole is a triazole antifungal exhibiting fungistatic activity against fungal pathogens.11,10,13 Like other triazoles, voriconazole binds to 14-alpha sterol demethylase, also known as CYP51, and inhibits the demethylation of lanosterol as part of the ergosterol synthesis pathway in yeast and other fungi. The lack of sufficient ergosterol disrupts fungal cell membrane function and limits fungal cell growth. With fungal growth limited, the host's immune system is able to clear the invading organism.
Target Actions Organism ACytochrome P450 51 antagonistinhibitorYeast - Absorption
The oral bioavailability is estimated to be 96% in healthy adults13. Population pharmacokinetic studies report a reduced bioavailability pediatric patients with a mean of 61.8% (range 44.6–64.5%) thought to be due to differences in first-pass metabolism or due to differences in diet 6. Of note, transplant patients also have reduced bioavailability but this is known to increase with time after transplantation and may be due in part to gastrointestinal upset from surgery and some transplant medications. Tmax is 1-2 hours with oral administration. When administered with a high-fat meal Cmax decreases by 34% and AUC by 24%. pH does not have an effect on absorption of voriconazole. Differences in Cmax and AUC have been observed between healthy adult males and females with Cmax increasing by 83% and AUC by 113% although this has not been observed to significantly impact medication safety profiles.
- Volume of distribution
The estimated volume of distribution of voriconazole is 4.6 L/kg 13. 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 Voriconazole is known to achieve therapeutic concentrations in many tissues including the brain, lungs, liver, spleen, kidneys, and heart.
- Protein binding
Voriconazole is 58% bound to plasma proteins 13.
- Metabolism
Voriconazole undergoes extensive hepatic metabolism through cytochrome enzymes CYP2C9, CYP2C19, and CYP3A4. CYP2C19 mediates N-oxidation with an apparent Km of 14 μM and an apparent Vmax of 0.22 nmol/min/nmol CYP2C19.8 Voriconazole N-oxide is the major circulating metabolite, accounting for 72% of radiolabeled metabolites found.13 CYP3A4 contributes to N-oxidation with a Km of 16 μM and Vmax of 0.05 nmol/min/nmol CYP3A4 as well as 4-hydroxylation with a Km of 11 μM and a Vmax of 0.10 nmol/min/nmol CYP3A4.8 CYP3A5 and CYP3A7 provide minor contributions to N-oxidation and 4-hydroxylation. The N-oxide and 4-hydroxylated metabolites undergo glucuronidation and are excreted through the urine with other minor glucuronidated metabolites.9
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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.13
- Half-life
Voriconazole follows non-linear kinetics and has a terminal half-life of elimination which is dose-dependent.13
- Clearance
The clearance of voriconazole is estimated to be a mean of 5.25-7 L/h in healthy adults for the linear portion of the drug's kinetics.6,7
- Adverse Effects
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Symptoms of overdose include photophobia and possible QTc prolongation.13,14 In case of overdose, supportive care and ECG monitoring are recommended. Activated charcoal may aid in the removal of unabsorbed drug. Voriconazole is cleared by hemodialysis at a rate of 121 mL/min which may be helpful in removing absorbed drug. Carcinogenicity studies found hepatocellular adenomas in female rats at doses of 50 mg/kg and hepatocellular carcinomas found in male rats at doses of 6 and 50 mg/kg. These doses are equivalent to 0.2 and 1.6 times the recommended maintenance dose (RMD). Studies in mice detected hepatocellular carcinomas in males at doses of 100 mg/kg or 1.4 times the RMD. Hepatocellular adenomas were detected in both male and female mice.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
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 Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The serum concentration of 1,2-Benzodiazepine can be increased when it is combined with Voriconazole. Abametapir 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 Abiraterone can be decreased when combined with Voriconazole. - Food Interactions
- Take separate from meals. Take voriconazole at least one hour before or after eating for optimal absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vfend Tablet, film coated 200 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU 
Vfend Injection, powder, lyophilized, for solution 10 mg/1mL Intravenous Roerig 2002-05-24 Not applicable US 
Vfend Tablet, film coated 200 mg Oral Pfizer Europe Ma Eeig 2021-02-11 Not applicable EU Vfend Tablet, film coated 50 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU Vfend Tablet, film coated 200 mg Oral Pfizer Europe Ma Eeig 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ach-voriconazole Tablet 200 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada 
Ach-voriconazole Tablet 50 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada Apo-voriconazole Tablet 200 mg Oral Apotex Corporation 2014-04-14 Not applicable Canada Apo-voriconazole Tablet 50 mg Oral Apotex Corporation 2014-04-14 Not applicable Canada Auro-voriconazole Tablet 200 mg Oral Auro Pharma Inc Not applicable Not applicable Canada
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 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strong)
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Photosensitizing Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Steroid Synthesis Inhibitors
- Triazole and tetrazole derivatives
- 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)
- Affected organisms
- Yeast and other fungi
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
- (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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Bellmann R, Smuszkiewicz P: Pharmacokinetics of antifungal drugs: practical implications for optimized treatment of patients. Infection. 2017 Dec;45(6):737-779. doi: 10.1007/s15010-017-1042-z. Epub 2017 Jul 12. [Article]
- 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. [Article]
- Roffey SJ, Cole S, Comby P, Gibson D, Jezequel SG, Nedderman AN, Smith DA, Walker DK, Wood N: The disposition of voriconazole in mouse, rat, rabbit, guinea pig, dog, and human. Drug Metab Dispos. 2003 Jun;31(6):731-41. [Article]
- Sanati H, Belanger P, Fratti R, Ghannoum M: A new triazole, voriconazole (UK-109,496), blocks sterol biosynthesis in Candida albicans and Candida krusei. Antimicrob Agents Chemother. 1997 Nov;41(11):2492-6. doi: 10.1128/AAC.41.11.2492. [Article]
- Sabo JA, Abdel-Rahman SM: Voriconazole: a new triazole antifungal. Ann Pharmacother. 2000 Sep;34(9):1032-43. doi: 10.1345/aph.19237. [Article]
- International Patent WO 98/58677: Pharmaceutical formulations containing voriconazole [Link]
- VFENDⓇ FDA Label [Link]
- Health Canada Approved Products: Vfend (voriconazole) multiple forms/routes [Link]
- VFend FDA Approval Letter [Link]
- FDA Approved Drug Products: VORICONAZOLE for injection, for intravenous use [Link]
- EMA Approved Products: Vfend (voriconazole) oral tablets [Link]
- FDA Approved Drug Products: VFEND (voriconazole) multiple forms/routes [Link]
- FDA Label VORICONAZOLE- voriconazole injection [File]
- 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
- PDB Entries
- 3mdt / 4uym / 4ze0 / 5hs1 / 6ay6 / 6h1o / 7ry8 / 7ry9 / 7ryb
- FDA label
- Download (321 KB)
- MSDS
- Download (57.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Aspergillosis / Candidemia 1 4 Completed Not Available Healthy Subjects (HS) 1 4 Completed Basic Science Fungal Infections 1 4 Completed Diagnostic Drug Drug Interaction (DDI) / Kidney Transplantation 1 4 Completed Health Services Research Healthy Subjects (HS) 2
Pharmacoeconomics
- Manufacturers
- Pfizer inc
- Matrix laboratories ltd
- Packagers
- Cardinal Health
- DSM Corp.
- Pfizer Inc.
- Dosage Forms
Form Route Strength Solution Intravenous 200.00 mg Injection, powder, lyophilized, for solution Intravenous 20000000 mg Tablet, coated Oral 5000000 mg Solution Intravenous 220.000 mg Powder, for solution Intravenous 200 MG Powder, for solution Intravenous 200 mg / vial Powder, for suspension Oral 200 mg / 5 mL Solution Intravenous 200.000 mg Tablet Oral 200 mg Tablet Oral 200.000 mg Tablet Oral 50 mg Powder Intravenous 200 mg/1vial Tablet, film coated Oral 200 MG Tablet, film coated Oral 50 MG Injection, powder, for solution Intravenous 10 mg/ml Injection, powder, for solution Intravenous Solution Parenteral 200 mg Powder, for suspension Oral 40 mg/ml Injection Intravenous Injection, solution Intravenous 200 mg Injection, powder, lyophilized, for solution Intravenous 200 mg Tablet, film coated Oral Injection, powder, for solution Parenteral Tablet, film coated Oral 100 MG Injection, powder, for solution Intravenous 200 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 Powder, for solution 200 MG Powder, for solution Powder, for suspension Oral Powder, for solution Parenteral 200 MG Injection Intravenous 200 mg Injection, solution Intravenous Injection Parenteral 200 mg Injection, solution, concentrate Intravenous 200 mg Tablet, coated Oral 50 mg Tablet, coated Oral 200 mg Powder Intravenous 40 mg/1ml Injection, powder, for solution Intravenous 200 mg/1vial - 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 US5116844 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
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) 12.7 Chemaxon pKa (Strongest Basic) 2.01 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.1663041 predictedDarkChem Lite v0.1.0 [M-H]- 174.20804 predictedDeepCCS 1.0 (2019) [M+H]+ 179.6872041 predictedDarkChem Lite v0.1.0 [M+H]+ 176.56604 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.9632041 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.12534 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Sanati H, Belanger P, Fratti R, Ghannoum M: A new triazole, voriconazole (UK-109,496), blocks sterol biosynthesis in Candida albicans and Candida krusei. Antimicrob Agents Chemother. 1997 Nov;41(11):2492-6. doi: 10.1128/AAC.41.11.2492. [Article]
- VFENDⓇ FDA Label [Link]
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
- Yanni SB, Annaert PP, Augustijns P, Bridges A, Gao Y, Benjamin DK Jr, Thakker DR: Role of flavin-containing monooxygenase in oxidative metabolism of voriconazole by human liver microsomes. Drug Metab Dispos. 2008 Jun;36(6):1119-25. doi: 10.1124/dmd.107.019646. Epub 2008 Mar 24. [Article]
- 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. [Article]
- Yamada T, Mino Y, Naito T, Kawakami J: Impact of flavin-containing monooxygenase 3 and CYP2C19 genotypes on plasma disposition and adverse effects of voriconazole administered orally in immunocompromised patients. J Infect Chemother. 2019 Dec;25(12):1019-1025. doi: 10.1016/j.jiac.2019.05.032. Epub 2019 Jun 22. [Article]
- Yanni SB, Annaert PP, Augustijns P, Ibrahim JG, Benjamin DK Jr, Thakker DR: In vitro hepatic metabolism explains higher clearance of voriconazole in children versus adults: role of CYP2C19 and flavin-containing monooxygenase 3. Drug Metab Dispos. 2010 Jan;38(1):25-31. doi: 10.1124/dmd.109.029769. [Article]
- Yanni SB, Annaert PP, Augustijns P, Bridges A, Gao Y, Benjamin DK Jr, Thakker DR: Role of flavin-containing monooxygenase in oxidative metabolism of voriconazole by human liver microsomes. Drug Metab Dispos. 2008 Jun;36(6):1119-25. doi: 10.1124/dmd.107.019646. Epub 2008 Mar 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- VFENDⓇ FDA Label [Link]
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- VFENDⓇ FDA Label [Link]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- VFENDⓇ FDA Label [Link]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54