Voriconazole

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Voriconazole (DB00582)

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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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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

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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	antagonist inhibitor	Yeast

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

Hover over products below to view reaction partners

• Voriconazole
  • Voriconazole N-Oxide
    • UK-51,060
      • UK-215,364
        • Voriconazole O-glucuronide derivative (1)
  • 4-Hydroxyvoriconazole
    • 4-Hydroxyvoriconazole 4-O-glucuronide

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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Toxicity

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

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be decreased when 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.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Voriconazole.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Voriconazole.
Acetaminophen	The metabolism of Acetaminophen can be decreased when 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.

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Food Interactions

• Take separate from meals. Take voriconazole at least one hour before or after eating for optimal absorption.

Products

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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
Vfend	Tablet, film coated	50 mg	Oral	Pfizer Europe Ma Eeig	2016-09-08	Not applicable
Vfend	Tablet, film coated	50 mg	Oral	Pfizer Europe Ma Eeig	2021-02-11	Not applicable
Vfend	Powder, for suspension	200 mg / 5 mL	Oral	Pfizer Canada Ulc	2008-07-17	Not applicable
Vfend	Tablet, film coated	50 mg	Oral	Pfizer Europe Ma Eeig	2021-02-11	Not applicable
Vfend	Tablet, film coated	50 mg	Oral	Pfizer Europe Ma Eeig	2016-09-08	Not applicable
Vfend	Tablet, film coated	200 mg	Oral	Pfizer Europe Ma Eeig	2016-09-08	Not applicable
Vfend	Tablet, film coated	200 mg	Oral	Pfizer Europe Ma Eeig	2016-09-08	Not applicable
Vfend	Tablet, film coated	200 mg	Oral	Pfizer Europe Ma Eeig	2021-02-11	Not applicable
Vfend	Tablet, film coated	200 mg	Oral	Pfizer Europe Ma Eeig	2021-02-11	Not applicable

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
Ach-voriconazole	Tablet	50 mg	Oral	Accord Healthcare Inc	Not applicable	Not applicable
Apo-voriconazole	Tablet	200 mg	Oral	Apotex Corporation	2014-04-14	Not applicable
Apo-voriconazole	Tablet	50 mg	Oral	Apotex Corporation	2014-04-14	Not applicable
Auro-voriconazole	Tablet	200 mg	Oral	Auro Pharma Inc	Not applicable	Not applicable
Auro-voriconazole	Tablet	50 mg	Oral	Auro Pharma Inc	Not applicable	Not applicable
Med-voriconazole	Tablet	200 mg	Oral	Generic Medical Partners Inc	Not applicable	Not applicable
Mylan-voriconazole	Tablet	200 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable
Mylan-voriconazole	Tablet	50 mg	Oral	Mylan Pharmaceuticals	Not applicable	Not applicable
PMS-voriconazole	Powder, for solution	200 mg / vial	Intravenous	Pharmascience Inc	Not applicable	Not applicable

Categories

ATC Codes

J02AC03 — Voriconazole

• J02AC — Triazole derivatives
• J02A — ANTIMYCOTICS FOR SYSTEMIC USE
• J02 — ANTIMYCOTICS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

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 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 / Hydrocarbon derivatives / Aromatic alcohols

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Substituents

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

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

(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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
6. 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]
7. 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]
8. 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]
9. 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]
10. 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]
11. Sabo JA, Abdel-Rahman SM: Voriconazole: a new triazole antifungal. Ann Pharmacother. 2000 Sep;34(9):1032-43. doi: 10.1345/aph.19237. [Article]
12. International Patent WO 98/58677: Pharmaceutical formulations containing voriconazole [Link]
13. VFENDⓇ FDA Label [Link]
14. Health Canada Approved Products: Vfend (voriconazole) multiple forms/routes [Link]
15. VFend FDA Approval Letter [Link]

External Links

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

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

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Aspergillosis / Candidemia	1
4	Completed	Not Available	Healthy Subjects (HS)	1
4	Completed	Basic Science	Infections, Fungal	1
4	Completed	Diagnostic	Drug Drug Interaction (DDI) / Kidney Transplantation	1
4	Completed	Health Services Research	Healthy Subjects (HS)	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
Injection, solution	Intravenous
Tablet	Oral	200 mg
Powder, for solution	Intravenous	200 MG
Powder, for suspension	Oral	200 mg / 5 mL
Powder, for suspension	Oral	40 MG/ML
Tablet	Oral	50 mg
Powder	Intravenous	200 mg/1vial
Injection, powder, for solution	Intravenous	10 mg/ml
Powder, for solution	Intravenous	200 mg / vial
Injection, powder, for solution	Intravenous
Solution	Parenteral
Tablet, film coated	Oral	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	Intravenous	200 mg / vial
Tablet, film coated	Oral	50 MG
Powder, for solution		200 MG
Powder, for solution
Powder, for suspension	Oral
Powder, for solution	Parenteral	200 MG
Injection	Parenteral
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
CA2295035	No	2005-04-19	2018-06-02
CA2035314	No	2000-01-18	2011-01-30
US5567817	No	1996-10-22	2016-05-24
US6632803	No	2003-10-14	2018-06-02

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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Details1. Cytochrome P450 51

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. 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]
2. 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]
3. 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]
4. 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]
5. 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]
6. 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]
7. 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]
8. 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]
9. VFENDⓇ FDA Label [Link]

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Drug created on June 13, 2005 13:24 / Updated on October 24, 2021 16:00