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    Chemistry

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    Also known as: 137234-62-9, Vfend, (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol, Uk-109496, (+/-)-voriconazole, Voriconazole vfend
    Molecular Formula
    C16H14F3N5O
    Molecular Weight
    349.31  g/mol
    InChI Key
    BCEHBSKCWLPMDN-MGPLVRAMSA-N
    FDA UNII
    USG4B1CD29
    Voriconazole
    A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.
    Voriconazole is an Azole Antifungal. The mechanism of action of voriconazole is as a Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 2C19 Inhibitor, and Cytochrome P450 2C9 Inhibitor.
    1 2D Structure

    Voriconazole

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
    2.1.2 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
    2.1.3 InChI Key
    BCEHBSKCWLPMDN-MGPLVRAMSA-N
    2.1.4 Canonical SMILES
    CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
    2.1.5 Isomeric SMILES
    C[C@@H](C1=NC=NC=C1F)[C@](CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
    2.2 Other Identifiers
    2.2.1 UNII
    USG4B1CD29
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Uk 109,496

    2. Uk 109496

    3. Uk-109,496

    4. Uk-109496

    5. Uk109,496

    6. Uk109496

    7. Vfend

    2.3.2 Depositor-Supplied Synonyms

    1. 137234-62-9

    2. Vfend

    3. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol

    4. Uk-109496

    5. (+/-)-voriconazole

    6. Voriconazole Vfend

    7. Uk-109,496

    8. Uk 109496

    9. Voriconzole

    10. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol

    11. Vcz

    12. Voriconazole, (+/-)-

    13. Chembl638

    14. Nsc-759888

    15. Jfu09i87tr

    16. Usg4b1cd29

    17. Cpd000466350

    18. (r-(r*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

    19. 4-pyrimidineethanol, Alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-, (alphar,betas)-

    20. Chebi:10023

    21. 173967-54-9

    22. Vrc

    23. Voriconazol

    24. Dsstox_cid_26485

    25. Dsstox_rid_81656

    26. Dsstox_gsid_46485

    27. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-((1h)-1,2,4-triazol-1-yl)-butan-2-ol

    28. (alphar,betas)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

    29. 4-pyrimidineethanol, Alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-, (r-(r*,s*))-

    30. Voriconazole Related Compound A

    31. 188416-29-7

    32. Voriconazolum

    33. Vorikonazole

    34. Voriconazole [usan:inn:ban]

    35. Drg-0301

    36. Smr000466350

    37. Cas-137234-62-9

    38. Vfend (tn)

    39. Vfend I.v.

    40. Unii-jfu09i87tr

    41. Pfizer

    42. Ncgc00164622-01

    43. Voriconazole Solution

    44. Voriconazole- Bio-x

    45. Voriconazole - Vfend

    46. (alphar,betas)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

    47. Voriconazole In Combination With Mgcd290

    48. Voriconazole [mi]

    49. Voriconazole [inn]

    50. Voriconazole [jan]

    51. Unii-usg4b1cd29

    52. Voriconazole [usan]

    53. Voriconazole [vandf]

    54. Schembl36233

    55. Voriconazole [mart.]

    56. Mls000759464

    57. Mls001424082

    58. Mls006010028

    59. Voriconazole [usp-rs]

    60. Voriconazole [who-dd]

    61. Voriconazole [ema Epar]

    62. Dtxsid5046485

    63. Voriconazole (jp17/usp/inn)

    64. Zinc14864

    65. Amy8903

    66. Voriconazole, >=98% (hplc)

    67. Bcpp000019

    68. Dtxsid201019420

    69. Hms2051n09

    70. Hms3260m22

    71. Hms3713f12

    72. Pharmakon1600-01502346

    73. Voriconazole [orange Book]

    74. Voriconazole [ep Monograph]

    75. Tox21_112241

    76. Tox21_500150

    77. Voriconazole [usp Monograph]

    78. Voriconazole 2.0 Mg/ml In Methanol

    79. Ac-823

    80. Bdbm50333117

    81. Nsc759888

    82. S1442

    83. Akos005145705

    84. Tox21_112241_1

    85. Ccg-100941

    86. Cs-1227

    87. Db00582

    88. Hy-w337569

    89. Ks-1157

    90. Nc00191

    91. Nsc 759888

    92. Ncgc00164622-02

    93. Ncgc00164622-04

    94. Ncgc00164622-06

    95. Ncgc00260835-01

    96. Bv164532

    97. Hy-76200

    98. ( Inverted Exclamation Marka)-voriconazole

    99. Voriconazole Related Compound A Rs [usp]

    100. Cs-0448910

    101. Sw197571-2

    102. V0116

    103. C07622

    104. D00578

    105. Ab00639948-04

    106. Ab00639948-06

    107. Ab00639948_07

    108. Ab00639948_08

    109. Voriconazole Related Compound A [usp-rs]

    110. Voriconazole, Vetranal(tm), Analytical Standard

    111. 234v629

    112. A807215

    113. Q412236

    114. J-006986

    115. Voriconazole Related Compound A [usp Impurity]

    116. Z2616414875

    117. Voriconazole, European Pharmacopoeia (ep) Reference Standard

    118. Voriconazole, United States Pharmacopeia (usp) Reference Standard

    119. (2r,3s)-2,3-bis(2,4-difluorophenyl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol

    120. 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl) Butan-2-ol

    121. 4-[[4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl]methylene]-1-oxo-1,3-thiazolidin-5-one

    122. Voriconazole, Pharmaceutical Secondary Standard: Certified Reference Material

    123. (.alpha.r,.beta.s)-a-(2,4-difluorophenyl)-5-fluoro-.beta.-methyl-.alpha.-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

    124. (2r,3s)-2-(2,4-difluoro-phenyl)-3-(5-fluoro-pyrimidin-4-yl)-1-[1,2,4]triazol-1-yl-butan-2-ol

    125. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1h-1,2,4-triazol-1-yl) Butan-2-ol

    126. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1h-1,2,4-triazol-1-yl)-2-butanol

    127. (2r,3s)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol

    128. 2r,3s-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol-4-pyrimidineethanol, ?-(2,4-difluorophenyl)-5-fluoro-?-methyl-?-(1h-1,2,4-triazol-1-ylmethyl)-,?(?r,?s)-

    129. 4-pyrimidineethanol, .alpha.-(2,4-difluorophenyl)-5-fluoro-.beta.-methyl-.alpha.-(1h-1,2,4-triazol-1-ylmethyl)-, (.alpha.r,.beta.s)-rel-

    130. 4-pyrimidineethanol, A-(2,4-difluorophenyl)-5-fluoro-.beta.-methyl-.alpha.-(1h-1,2,4-triazol-1-ylmethyl)-, (.alpha.r,.beta.s)-

    131. 4-pyrimidineethanol, Alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-, (alphar,betas)-rel-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 349.31 g/mol
    Molecular Formula C16H14F3N5O
    XLogP31.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass349.11504457 g/mol
    Monoisotopic Mass349.11504457 g/mol
    Topological Polar Surface Area76.7 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity448
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameVfend
    PubMed HealthVoriconazole (By mouth)
    Drug ClassesAntifungal
    Drug LabelVFEND (voriconazole), a triazole antifungal agent, is available as a lyophilized powder for solution for intravenous infusion, film-coated tablets for oral administration, and as a powder for oral suspension. The structural formula is:Voriconazole...
    Active IngredientVoriconazole
    Dosage FormTablet; Injectable; For suspension
    Routeinjection; oral; Iv (infusion); Oral; iv (infusion)
    Strength200mg/5ml; 200mg; 200mg/vial; 50mg
    Market StatusPrescription
    CompanyPfizer

    2 of 4  
    Drug NameVoriconazole
    PubMed HealthVoriconazole
    Drug ClassesAntifungal
    Drug LabelVFEND (voriconazole), a triazole antifungal agent, is available as a lyophilized powder for solution for intravenous infusion, film-coated tablets for oral administration, and as a powder for oral suspension. The structural formula is:Voriconazole...
    Active IngredientVoriconazole
    Dosage FormTablet; Injectable; For suspension
    RouteIv (infusion); Oral
    Strength200mg/5ml; 200mg; 200mg/vial; 50mg
    Market StatusPrescription
    CompanyMylan Pharms; Sandoz; Teva Pharms

    3 of 4  
    Drug NameVfend
    PubMed HealthVoriconazole (By mouth)
    Drug ClassesAntifungal
    Drug LabelVFEND (voriconazole), a triazole antifungal agent, is available as a lyophilized powder for solution for intravenous infusion, film-coated tablets for oral administration, and as a powder for oral suspension. The structural formula is:Voriconazole...
    Active IngredientVoriconazole
    Dosage FormTablet; Injectable; For suspension
    Routeinjection; oral; Iv (infusion); Oral; iv (infusion)
    Strength200mg/5ml; 200mg; 200mg/vial; 50mg
    Market StatusPrescription
    CompanyPfizer

    4 of 4  
    Drug NameVoriconazole
    PubMed HealthVoriconazole
    Drug ClassesAntifungal
    Drug LabelVFEND (voriconazole), a triazole antifungal agent, is available as a lyophilized powder for solution for intravenous infusion, film-coated tablets for oral administration, and as a powder for oral suspension. The structural formula is:Voriconazole...
    Active IngredientVoriconazole
    Dosage FormTablet; Injectable; For suspension
    RouteIv (infusion); Oral
    Strength200mg/5ml; 200mg; 200mg/vial; 50mg
    Market StatusPrescription
    CompanyMylan Pharms; Sandoz; Teva Pharms

    4.2 Drug Indication

    For the treatment of esophageal candidiasis, cadidemia, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp.

    FDA Label

    Voriconazole is a broad spectrum, triazole antifungal agent and is indicated in adults and children aged 2 years and above as follows:

    - treatment of invasive aspergillosis;

    - treatment of candidaemia in non-neutropenic patients;

    - treatment of fluconazole-resistant serious invasive Candida infections (including C. krusei);

    - treatment of serious fungal infections caused by Scedosporium spp. and Fusarium spp.

    Voriconazole should be administered primarily to patients with progressive, possibly life-threatening infections.

    Prophylaxis of invasive fungal infections in high risk allogeneic hematopoietic stem cell transplant (HSCT)

    recipients.

    Voriconazole, is a broad spectrum, triazole antifungal agent and is indicated in adults and children aged 2 years and above as follows:

    - treatment of invasive aspergillosis;

    - treatment of in candidaemianon-neutropenic patients;

    - treatment of fluconazole-resistant serious invasive Candida infections (including C. krusei);

    - Treatment of serious fungal infections caused by Scedosporium spp. and Fusarium spp.

    Vfend should be administered primarily to patients with progressive, possibly life-threatening infections.

    Prophylaxis of invasive fungal infections in high risk allogeneic hematopoietic stem cell transplant (HSCT) recipients.

    Voriconazole is a broad-spectrum, triazole antifungal agent and is indicated in adults and children aged two years and above as follows:

    - treatment of invasive aspergillosis;

    - treatment of candidaemia in non-neutropenic patients;

    - treatment of fluconazole-resistant serious invasive Candida infections (including C. krusei);

    - Treatment of serious fungal infections caused by Scedosporium spp. and Fusarium spp.

    Voriconazole Accord should be administered primarily to patients with progressive, possibly life-threatening infections.

    Treatment of candidaemia in non-neutropenic patients, Treatment of fluconazole-resistant serious invasive Candida infections (including C. krusei), Treatment of invasive aspergillosis, Treatment of serious fungal infections caused by Scedosporium spp. and Fusarium spp.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Voriconazole is a fungistatic triazole antifungal used to treat infections by inhibiting fungal growth. It is known to cause hepatotoxic and photosensitivity reactions in some patients.

    5.2 MeSH Pharmacological Classification

    14-alpha Demethylase Inhibitors

    Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    Cytochrome P-450 CYP3A Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    VORICONAZOLE
    5.3.2 FDA UNII
    JFU09I87TR
    5.3.3 Pharmacological Classes
    Azoles [CS]; Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; Azole Antifungal [EPC]
    5.4 ATC Code

    J02AC03

    J02AC03

    J02AC03

    J02AC03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    J - Antiinfectives for systemic use

    J02 - Antimycotics for systemic use

    J02A - Antimycotics for systemic use

    J02AC - Triazole and tetrazole derivatives

    J02AC03 - Voriconazole

    5.5 Absorption, Distribution and Excretion

    Absorption

    The oral bioavailability is estimated to be 96% in healthy adults. Population pharmacokinetic studies report a reduced bioavailability pediatric patients with a mean of 61.8% (range 44.664.5%) thought to be due to differences in first-pass metabolism or due to differences in diet. 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.

    Route of Elimination

    Voriconazole is eliminated via hepatic metabolism with less than 2% of the dose excreted unchanged in the urine.

    Volume of Distribution

    The estimated volume of distribution of voriconazole is 4.6 L/kg. Population pharmacokinetic studies estimate the median volume of distribution to be 77.6 L with the central compartment estimated at 1.07 L/kg Voriconazole is known to achieve therapeutic concentrations in many tissues including the brain, lungs, liver, spleen, kidneys, and heart.

    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.

    5.6 Metabolism/Metabolites

    Voriconazole undergoes extensive hepatic metabolism through cytochrome enzymes CYP2C9, CYP2C19, and CYP3A4. CYP2C19 mediates N-oxidation with an apparent Km of 14 M and an apparent Vmax of 0.22 nmol/min/nmol CYP2C19. Voriconazole N-oxide is the major circulating metabolite, accounting for 72% of radiolabeled metabolites found. CYP3A4 contributes to N-oxidation with a Km of 16 M and Vmax of 0.05 nmol/min/nmol CYP3A4 as well as 4-hydroxylation with a Km of 11 M and a Vmax of 0.10 nmol/min/nmol CYP3A4. 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.

    Voriconazole has known human metabolites that include Hydroxymethyl Voriconazole and Voriconazole N-Oxide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Voriconazole follows non-linear kinetics and has a terminal half-life of elimination which is dose-dependent.

    5.8 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. 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.

    API Reference Price

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    02-Jan-2021
    29-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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    DOSAGE - TABLET;ORAL - 200MG

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