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
Thumb
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
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.

TargetActionsOrganism
ACytochrome P450 51
antagonist
inhibitor
Yeast
Absorption

The oral bioavailability is estimated to be 96% (CV 13%).

Volume of distribution
  • 4.6 L/kg
Protein binding

58%

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.

Hover over products below to view reaction partners

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/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYPC19*17(T;T) / (C;T)C > TEffect Directly StudiedPatients with this genotype in CYP2C19 are ultra fast metabolizers and require higer doses of voriconazole to attain the therapeutic effect.Details
Cytochrome P450 2C19CYP2C19*2Not Available681G>ADirectly Studied EffectThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of voriconazole.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>ADirectly Studied EffectThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of voriconazole.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*4Not Available1A>GADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*6Not Available395G>AADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all ADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GADR InferredPoor drug metabolizer, may lead to hepatotoxicity, visual disturbances, visual hallucinations, and other neurologic disordersDetails

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.
DrugInteraction
AbametapirThe serum concentration of Voriconazole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Voriconazole can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Voriconazole.
AbirateroneThe metabolism of Voriconazole can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Voriconazole.
AcebutololThe risk or severity of QTc prolongation can be increased when Voriconazole is combined with Acebutolol.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Voriconazole.
AcetohexamideThe serum concentration of Acetohexamide can be increased when it is combined with Voriconazole.
Acetyl sulfisoxazoleThe metabolism of Voriconazole can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Voriconazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VfendInjection, powder, for solution200 mgIntravenousPfizer2002-03-19Not applicableEU flag
VfendTablet50 mgOralPfizer2002-03-19Not applicableEU flag
VfendPowder, for suspensionOralPfizer Canada Ulc2008-07-17Not applicableCanada flag
VfendTablet200 mgOralPfizer2002-03-19Not applicableEU flag
VfendTablet200 mgOralPfizer2002-03-19Not applicableEU flag
VfendTablet50 mgOralPfizer2002-03-19Not applicableEU flag
VfendTablet, film coated50 mg/1OralCardinal Health2002-05-242012-01-31US flag
VfendPowder, for suspension40 mg/1mLOralRoerig2003-03-28Not applicableUS flag
VfendTabletOralPfizer Canada Ulc2004-11-12Not applicableCanada flag
VfendTablet50 mgOralPfizer2002-03-19Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-voriconazoleTabletOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-voriconazoleTabletOralAccord Healthcare IncNot applicableNot applicableCanada flag
Apo-voriconazoleTabletOralApotex Corporation2014-04-14Not applicableCanada flag
Apo-voriconazoleTabletOralApotex Corporation2014-04-14Not applicableCanada flag
Auro-voriconazoleTabletOralAuro Pharma IncNot applicableNot applicableCanada flag
Auro-voriconazoleTabletOralAuro Pharma IncNot applicableNot applicableCanada flag
Med-voriconazoleTabletOralGeneric Medical Partners IncNot applicableNot applicableCanada flag
Mylan-voriconazoleTabletOralMylan PharmaceuticalsNot applicableNot applicableCanada flag
Mylan-voriconazoleTabletOralMylan PharmaceuticalsNot applicableNot applicableCanada flag
PMS-voriconazolePowder, for solutionIntravenousPharmascience IncNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

Categories

ATC Codes
J02AC03 — Voriconazole
Drug Categories
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[[email protected]@H](C1=NC=NC=C1F)[[email protected]](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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Pfizer Canada: Voriconazole Product Monograph [Link]
  7. International Patent WO 98/58677: Pharmaceutical formulations containing voriconazole [Link]
  8. VFENDⓇ FDA Label [Link]
  9. Health Canada Approved Products: Vfend (voriconazole) multiple forms/routes [Link]
Human Metabolome Database
HMDB0014720
KEGG Drug
D00578
KEGG Compound
C07622
PubChem Compound
71616
PubChem Substance
46506421
ChemSpider
64684
BindingDB
50333117
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAspergillosis / Candidemia1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailableInfections, Fungal1
4CompletedBasic ScienceInfections, Fungal1
4CompletedDiagnosticDrug Drug Interaction (DDI) / Transplantation, Kidney1
4CompletedHealth Services ResearchHealthy Volunteers1
4CompletedPreventionProphylaxis Of Invasive Fungal Infections1
4CompletedTreatmentAntimycotic for Systematic Use1
4CompletedTreatmentAspergillosis / Candidiasis / Cryptococcosis1
4CompletedTreatmentCandidemia / Candidiasis, Invasive1

Pharmacoeconomics

Manufacturers
  • Pfizer inc
  • Matrix laboratories ltd
Packagers
  • Cardinal Health
  • DSM Corp.
  • Pfizer Inc.
Dosage Forms
FormRouteStrength
TabletOral
InjectionIntravenous200 mg
Powder, for solutionIntravenous
Injection, solutionIntravenous200 mg
Injection, powder, for solutionIntravenous200 mg
Powder, for solutionIntravenous200 MG
Powder, for suspensionOral
Powder, for suspensionOral40 mg/ml
TabletOral200 mg
TabletOral50 mg
Tablet, coated200 mg
Tablet
Tablet, film coated50 mg
SolutionParenteral200 mg
Powder
Tablet, film coatedOral100 MG
Injection, powder, for solutionIntravenous10 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous10 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous200 mg/1
Powder, for suspensionOral40 mg/1mL
SuspensionOral40 mg/1mL
TabletOral200 mg/1
TabletOral50 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral200 mg
Tablet, film coatedOral50 mg
PowderIntravenous
Powder, for solutionParenteral200 MG
Powder, for solution200 MG
Tablet, coated50 mg
Tablet, coatedOral50 mg
Injection, powder, lyophilized, for solutionIntravenous200 mg
Tablet, coatedOral200 mg
Tablet, film coated200 mg
Injection200 mg
Prices
Unit descriptionCostUnit
Vfend 40 mg/ml Suspension 75ml Bottle870.72USD bottle
Vfend iv 200 mg vial143.5USD vial
Vfend 200 mg tablet49.74USD tablet
Vfend 50 mg tablet12.43USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5116844No1992-05-262009-08-11US flag
CA2295035No2005-04-192018-06-02Canada flag
CA2035314No2000-01-182011-01-30Canada flag
US5567817No1996-10-222016-05-24US flag
US6632803No2003-10-142018-06-02US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134 °CPfizer Canada Product Monograph
water solubilityLowPatent WO 98/58677
Predicted Properties
PropertyValueSource
Water Solubility0.0978 mg/mLALOGPS
logP1.65ALOGPS
logP1.82ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.72 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.28 m3·mol-1ChemAxon
Polarizability30.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9047
Caco-2 permeable+0.7219
P-glycoprotein substrateSubstrate0.591
P-glycoprotein inhibitor INon-inhibitor0.6113
P-glycoprotein inhibitor IINon-inhibitor0.8195
Renal organic cation transporterNon-inhibitor0.5354
CYP450 2C9 substrateNon-substrate0.727
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5792
CYP450 1A2 substrateNon-inhibitor0.7491
CYP450 2C9 inhibitorInhibitor0.5203
CYP450 2D6 inhibitorNon-inhibitor0.8315
CYP450 2C19 inhibitorInhibitor0.5784
CYP450 3A4 inhibitorNon-inhibitor0.7011
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6649
Ames testNon AMES toxic0.7019
CarcinogenicityNon-carcinogens0.776
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3469 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8791
hERG inhibition (predictor II)Non-inhibitor0.6282
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fh9-2593000000-630f0453fb0da8e2745d

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. 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
  1. 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
  1. 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
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]
Details
5. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. 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
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. Flockhart Table of Drug Interactions [Link]
  4. Drug Interactions & Labeling - FDA [Link]
  5. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  6. Voriconazole FDA label [File]
Details
7. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  4. 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
  1. 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
  1. Flockhart Table of Drug Interactions [Link]

Drug created on June 13, 2005 07:24 / Updated on September 24, 2020 02:08

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates