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Voriconazole information


Voriconazole
Clinical data
Pronunciation/vɒrɪˈkɒnəzl/ vorr-i-KON-ə-zohl
Trade namesVfend, others
AHFS/Drugs.comMonograph
MedlinePlusa605022
License data
  • US DailyMed: Voriconazole
Pregnancy
category
  • AU: B3
Routes of
administration
Intravenous, by mouth
ATC code
  • J02AC03 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability96% (oral)
Protein binding58%
MetabolismLiver: CYP2C19 (significant involvement), also CYP2C9, CYP3A4
MetabolitesVoriconazole N-oxide (major; minimal antifungal activity)
Elimination half-lifeDose-dependent
ExcretionUrine (80–83%)[2]
Identifiers
IUPAC name
  • (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
CAS Number
  • 137234-62-9 checkY
PubChem CID
  • 71616
DrugBank
  • DB00582 checkY
ChemSpider
  • 64684 checkY
UNII
  • JFU09I87TR
KEGG
  • D00578 checkY
ChEBI
  • CHEBI:10023 checkY
ChEMBL
  • ChEMBL638 checkY
CompTox Dashboard (EPA)
  • DTXSID5046485 Edit this at Wikidata
ECHA InfoCard100.157.870 Edit this at Wikidata
Chemical and physical data
FormulaC16H14F3N5O
Molar mass349.317 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Fc1cncnc1[C@@H]([C@@](O)(c2ccc(F)cc2F)Cn3ncnc3)C
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 checkY
  • Key:BCEHBSKCWLPMDN-MGPLVRAMSA-N checkY
  (verify)

Voriconazole, sold under the brand name Vfend among others, is an antifungal medication used to treat a number of fungal infections.[3] This includes aspergillosis, candidiasis, coccidioidomycosis, histoplasmosis, penicilliosis, and infections by Scedosporium or Fusarium.[3] It can be taken by mouth or used by injection into a vein.[3]

Common side effects include vision problems, nausea, abdominal pain, rash, headache, and seeing or hearing things that are not present.[3] Use during pregnancy may result in harm to the baby.[3] It is in the triazole family of medications.[3] It works by affecting fungal metabolism and fungal cell membranes.[3]

Voriconazole was patented in 1990 and approved for medical use in the United States in 2002.[4][5] It is on the World Health Organization's List of Essential Medicines.[6]

  1. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. ^ Cite error: The named reference Vfend FDA label was invoked but never defined (see the help page).
  3. ^ a b c d e f g "Voriconazole". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
  4. ^ Kendig EL, Wilmott RW, Chernick V (2012). Kendig and Chernick's Disorders of the Respiratory Tract in Children. Elsevier Health Sciences. p. 539. ISBN 978-1437719840.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Itraconazole

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a broader spectrum of activity than fluconazole (but not as broad as voriconazole or posaconazole). In particular, it is active against Aspergillus, which...

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Coccidioides immitis

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further evaluation. Voriconazole is also being studied in salvage therapy for refractory cases. A case report indicated that voriconazole in combination with...

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Naegleriasis

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pools Treatment Miltefosine, fluconazole, amphotericin B, posaconazole, voriconazole, targeted temperature management Prognosis 98.5% fatality rate; some...

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Cortisol

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voriconazole, posaconazole, and caspofungin; however, some antifungal resistance has been shown in amphotericin B, itraconazole, and voriconazole. In...

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(April 2009). "Lack of allergic cross-reactivity between fluconazole and voriconazole" (PDF). Antimicrobial Agents and Chemotherapy. 53 (4): 1715–1716. doi:10...

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List of human disease case fatality rates

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October 2012). "Treatment of Granulomatous Amoebic Encephalitis with Voriconazole and Miltefosine in an Immunocompetent Soldier". The American Journal...

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Azole

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pharmacokinetics, analogues were developed. Second-generation triazoles, including voriconazole, posaconazole and ravuconazole, are more potent and more active against...

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Imidazole

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azoles is the triazoles, which includes fluconazole, itraconazole, and voriconazole. The difference between the imidazoles and the triazoles involves the...

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Pichia kudriavzevii

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 guillermondii and C. rugosa. P. kudriavzevii can be successfully treated with voriconazole, amphotericin B, and echinocandins (micafungin, caspofungin, and anidulafungin)...

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Ergotamine

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indinavir), certain azole antifungals (e.g., ketoconazole, itraconazole, voriconazole) delavirdine, efavirenz, or a 5-HT1 receptor agonist (e.g., sumatriptan)...

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Esophageal candidiasis

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be used alternatively. Other oral triazoles, such as itraconazole and voriconazole can be other options. Amphotericin B can be used in nonresponsive cases...

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Aspergillosis

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current medical treatments for aggressive invasive aspergillosis include voriconazole and liposomal amphotericin B in combination with surgical debridement...

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Lansoprazole

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Epidermophyton floccosum

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antifungal treatment, such as the use of terbinafine, itraconazole, voriconazole, and ketoconazole, is often effective. E. floccosum is one of the 2 species...

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Hemoptysis, chest pain Chest X-ray and CT, microscopy by silver stains Voriconazole and liposomal amphotericin B in combination with surgical debridement...

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Anidulafungin

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treating invasive Aspergillus infection when used in combination with voriconazole. It is a member of the class of antifungal drugs known as the echinocandins;...

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Triazole

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triazole antifungal drugs include fluconazole, isavuconazole, itraconazole, voriconazole, pramiconazole, ravuconazole, and posaconazole and triazole plant-protection...

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Coccidioidomycosis

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person's bones and joints. The antifungal medications posaconazole and voriconazole have also been used to treat coccidioidomycosis. Because the symptoms...

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Candida auris

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fluconazole and a range of 3–73% of C. auris isolates are resistant to voriconazole, while other triazoles (posaconazole, itraconazole, and isavuconazole)...

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Porphyria

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