Array ( [0] => {{Short description|Triazole antifungical drug}} [1] => {{Drugbox [2] => | Watchedfields = changed [3] => | verifiedrevid = 470631790 [4] => | image = Voriconazole structure.svg [5] => | width = [6] => | alt = [7] => | image2 = Voriconazole ball-and-stick model.png [8] => | width2 = [9] => | alt2 = [10] => [11] => [12] => | pronounce = {{IPAc-en|v|ɒr|ᵻ|ˈ|k|ɒ|n|ə|z|oʊ|l}} {{respell|vorr-i|KON|ə-zohl}} [13] => | tradename = Vfend, others [14] => | Drugs.com = {{drugs.com|monograph|voriconazole}} [15] => | MedlinePlus = a605022 [16] => | DailyMedID = Voriconazole [17] => | pregnancy_AU = B3 [18] => | pregnancy_category = [19] => | routes_of_administration = [[Intravenous therapy|Intravenous]], [[Oral administration|by mouth]] [20] => | ATC_prefix = J02 [21] => | ATC_suffix = AC03 [22] => | ATC_supplemental = [23] => [24] => | legal_AU = S4 [25] => | legal_AU_comment = {{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}} [26] => | legal_US = Rx-only [27] => | legal_EU = Rx-only [28] => | legal_status = Rx-only [29] => [30] => [31] => | bioavailability = 96% (oral) [32] => | protein_bound = 58% [33] => | metabolism = [[Liver]]: [[CYP2C19]] (significant involvement), also [[CYP2C9]], [[CYP3A4]] [34] => | metabolites = Voriconazole ''N''-oxide (major; minimal antifungal activity) [35] => | elimination_half-life = Dose-dependent [36] => | excretion = Urine (80–83%) [37] => [38] => [39] => | CAS_number_Ref = {{cascite|correct|??}} [40] => | CAS_number = 137234-62-9 [41] => | PubChem = 71616 [42] => | DrugBank_Ref = {{drugbankcite|correct|drugbank}} [43] => | DrugBank = DB00582 [44] => | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} [45] => | ChemSpiderID = 64684 [46] => | UNII_Ref = {{fdacite|correct|FDA}} [47] => | UNII = JFU09I87TR [48] => | KEGG_Ref = {{keggcite|correct|kegg}} [49] => | KEGG = D00578 [50] => | ChEBI_Ref = {{ebicite|correct|EBI}} [51] => | ChEBI = 10023 [52] => | ChEMBL_Ref = {{ebicite|correct|EBI}} [53] => | ChEMBL = 638 [54] => | synonyms = [55] => [56] => [57] => | IUPAC_name = (2''R'',3''S'')-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1''H''-1,2,4-triazol-1-yl)butan-2-ol [58] => | C=16 | H=14 | F=3 | N=5 | O=1 [59] => | SMILES = Fc1cncnc1[C@@H]([C@@](O)(c2ccc(F)cc2F)Cn3ncnc3)C [60] => | StdInChI_Ref = {{stdinchicite|correct|chemspider}} [61] => | StdInChI = 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 [62] => | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} [63] => | StdInChIKey = BCEHBSKCWLPMDN-MGPLVRAMSA-N [64] => }} [65] => [66] => '''Voriconazole''', sold under the brand name '''Vfend''' among others, is an [[antifungal medication]] used to treat a number of [[fungal infections]]. This includes [[aspergillosis]], [[candidiasis]], [[coccidioidomycosis]], [[histoplasmosis]], [[penicilliosis]], and infections by ''[[Scedosporium]]'' or ''[[Fusarium]]''. It can be taken [[oral administration|by mouth]] or used by [[intravenous infusion|injection into a vein]]. [67] => [68] => [69] => Common side effects include vision problems, nausea, abdominal pain, rash, headache, and [[hallucinations|seeing or hearing things that are not present]].{{cite web|title=Voriconazole|url=https://www.drugs.com/monograph/voriconazole.html|publisher=The American Society of Health-System Pharmacists|access-date= 8 December 2017}} Use during [[pregnancy]] may result in harm to the baby. It is in the [[triazole]] family of medications. It works by affecting fungal metabolism and fungal [[cell membrane]]s. [70] => [71] => [72] => Voriconazole was patented in 1990 and approved for medical use in the United States in 2002.{{cite book| vauthors = Kendig EL, Wilmott RW, Chernick V |title=Kendig and Chernick's Disorders of the Respiratory Tract in Children|date=2012|publisher=Elsevier Health Sciences|isbn=978-1437719840|page=539|url=https://books.google.com/books?id=w1xRGEXZ_bIC&pg=PA539|language=en}}{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=503 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA503 }} It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }} [73] => [74] => ==Medical uses== [75] => Voriconazole is used to treat invasive [[aspergillosis]] and [[candidiasis]] and fungal infections caused by ''[[Scedosporium]]'' and ''[[Fusarium]]'' species, which may occur in [[Immunodeficiency|immunocompromised]] patients, including people undergoing allogeneic [[bone marrow transplant]] (BMT), who have [[Hematological malignancy|hematologic cancers]] or who undergo [[organ transplant]]s.{{cite web|title=Vfend tablet and powder|url=https://www.medicines.org.uk/emc/medicine/10059|publisher=UK Electronic Medicines Compendium|access-date=30 July 2017|language=en|date=January 2017}}{{cite journal | vauthors = Patterson TF, Thompson GR, Denning DW, Fishman JA, Hadley S, Herbrecht R, Kontoyiannis DP, Marr KA, Morrison VA, Nguyen MH, Segal BH, Steinbach WJ, Stevens DA, Walsh TJ, Wingard JR, Young JA, Bennett JE | display-authors = 6 | title = Practice Guidelines for the Diagnosis and Management of Aspergillosis: 2016 Update by the Infectious Diseases Society of America | journal = Clinical Infectious Diseases | volume = 63 | issue = 4 | pages = e1–e60 | date = August 2016 | pmid = 27365388 | pmc = 4967602 | doi = 10.1093/cid/ciw326 | author-link7 = Dimitrios Kontoyiannis }}{{cite journal | vauthors = Omrani AS, Almaghrabi RS | title = Complications of hematopoietic stem transplantation: Fungal infections | journal = Hematology/Oncology and Stem Cell Therapy | volume = 10 | issue = 4 | pages = 239–244 | date = December 2017 | pmid = 28636889 | doi = 10.1016/j.hemonc.2017.05.013 | doi-access = free }}{{cite journal | vauthors = 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 | display-authors = 6 | title = Voriconazole versus amphotericin B for primary therapy of invasive aspergillosis | journal = The New England Journal of Medicine | volume = 347 | issue = 6 | pages = 408–415 | date = August 2002 | pmid = 12167683 | doi = 10.1056/NEJMoa020191 | hdl-access = free | hdl = 2066/185528 }} [76] => [77] => It is also used to prevent fungal infection in people as they undergo BMT. [78] => [79] => It is also the recommended treatment for the CNS fungal infections transmitted by epidural injection of contaminated steroids.{{cite web | title = Interim Treatment Guidance for Central Nervous System and Parameningeal Infections Associated with Injection of Contaminated Steroid Products | url = https://www.cdc.gov/hai/outbreaks/clinicians/index.html | publisher = Centers for Disease Control and Prevention | access-date = 6 November 2016}} [80] => [81] => It can be taken by mouth or given in a doctor's office or clinic by intravenous infusion. [82] => [83] => ==Contraindications== [84] => It is toxic to the fetus; pregnant women should not take it and women taking it should not become pregnant.{{cite web | title=Vfend- voriconazole tablet, film coated Vfend- voriconazole injection, powder, lyophilized, for solution Vfend- voriconazole powder, for suspension | website=DailyMed | date=16 September 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ce3ef5cf-3087-4d92-9d94-9eb8287228db | access-date=15 October 2020}} [85] => [86] => People who have hereditary intolerance for [[galactose]], Lapp lactase deficiency, or [[glucose-galactose malabsorption]] should not take this drug. It should be used with caution in people with arrhythmias or long QT. [87] => [88] => No dose adjustment is necessary for renal impairment or advanced age, but children seem to clear voriconazole faster than adults and drug levels may need monitoring.{{cite journal | vauthors = Smith J, Safdar N, Knasinski V, Simmons W, Bhavnani SM, Ambrose PG, Andes D | title = Voriconazole therapeutic drug monitoring | journal = Antimicrobial Agents and Chemotherapy | volume = 50 | issue = 4 | pages = 1570–1572 | date = April 2006 | pmid = 16569888 | pmc = 1426935 | doi = 10.1128/AAC.50.4.1570-1572.2006 }} [89] => [90] => ==Side effects== [91] => The labels carry several warnings of the risk of [[injection site reaction]]s, [[hypersensitivity]] reactions; [[kidney damage|kidney]], [[Liver damage|liver]], and [[pancreatitis|pancreas]] damage; trouble with vision; and adverse effects in skin including damage due to [[phototoxicity]], [[squamous cell skin cancer]], and [[Stevens–Johnson syndrome]]; in long-term use there is a warning of the risk of [[Skeletal fluorosis|bone fluorosis]] and [[periostitis]] especially in elderly patients.{{cite journal | vauthors = Stefan S, Altork N, Alzedaneen Y, Whitlatch H, Munir KM | title = Voriconazole-Induced Diffuse Periostitis | language = English | journal = AACE Clinical Case Reports | volume = 8 | issue = 5 | pages = 191–193 | date = 2022-09-01 | pmid = 36189133 | pmc = 9508586 | doi = 10.1016/j.aace.2022.05.001 }}{{cite journal | vauthors = Guarascio AJ, Bhanot N, Min Z | title = Voriconazole-associated periostitis: Pathophysiology, risk factors, clinical manifestations, diagnosis, and management | journal = World Journal of Transplantation | volume = 11 | issue = 9 | pages = 356–371 | date = September 2021 | pmid = 34631468 | pmc = 8465512 | doi = 10.5500/wjt.v11.i9.356 | doi-access = free }} [92] => [93] => Additionally, very common adverse effects, occurring in more than 10% of people, include peripheral edema, headaches, trouble breathing, diarrhea, vomiting, abdominal pain, nausea, rashes, and fever. [94] => [95] => Common adverse effects, occurring in between 1 and 10% of people, include sinus infections, low numbers of white and red blood cells ([[agranulocytosis]], [[pancytopenia]], [[thrombocytopenia]], [[leukopenia]], and [[anemia]]), low blood sugar, reduced amount of potassium and sodium, depression, hallucinations, anxiety, insomnia, agitation, confusion, convulsions, fainting, tremor, weakness, tingling, sleepiness, dizziness, bleeding retina, irregular heart beats, slow or fast heart beats, low blood pressure, inflamed veins, acute respiratory distress syndrome, pulmonary edema, inflamed lips, swollen face, stomach upset, constipation, gingivitis, jaundice, hair loss, flaky skin, itchiness, red skin, back pain, chest pain, and chills. [96] => [97] => == Interactions == [98] => [99] => Being metabolized by [[liver|hepatic]] [[cytochrome P450]], voriconazole interacts with many drugs. Voriconazole should not be used in conjunction with many drugs (including [[sirolimus]], [[rifampicin]], [[rifabutin]], [[carbamazepine]], [[quinidine]] and [[ergot]] alkaloids) and dose adjustments and/or monitoring should be done when coadministered with others (including [[fluconazole]], [[warfarin]], [[ciclosporin]], [[tacrolimus]], [[omeprazole]], and [[phenytoin]]). Voriconazole may be safely administered with [[cimetidine]], [[ranitidine]], [[indinavir]], [[macrolide]] antibiotics, [[mycophenolic acid|mycophenolate]], [[digoxin]] and [[prednisolone]]. [100] => [101] => ==Pharmacology== [102] => [103] => ===Pharmacokinetics=== [104] => Voriconazole is well absorbed orally with a [[bioavailability]] of 96%, allowing patients to be switched between intravenous and oral administration.{{cn|date=December 2022}} [105] => [106] => ==History== [107] => Pfizer brought the drug to market as Vfend. A generic version of the tablet form of voriconazole was introduced in the US in 2011 after Pfizer and Mylan settled litigation under the [[Hatch-Waxman Act]]; a generic version of the injectable form was introduced in 2012. In Europe patent protection expired in 2011 and pediatric administrative exclusivity expired in Europe in 2016.{{cite news|title=Vfend loses its paediatric protection|url=https://www.imshealth.com/files/web/Market%20Insights/Generic%20Lifecycle%20Management/INN%20Analysis/Pipeline%20Watch%20Archives/Pipeline_Wactch_Gen_22_Jul_2016.pdf|work=IMS Health Generics Bulletin|date=22 July 2016}} [108] => [109] => ==Society and culture== [110] => [111] => ===Brand names=== [112] => As of July 2017, the medication is marketed under the following names worldwide: Cantex, Pinup, Vedilozin, Vfend, Vodask, Volric, Voramol, Voriconazol, Voriconazole, Voriconazolum, Voricostad, Vorikonazol, Voritek, Voriz, Vornal, and Vosicaz.{{cite web|title=Voriconazole international brand names|url=https://www.drugs.com/international/voriconazole.html|publisher=Drugs.com|access-date=30 July 2017}} [113] => [114] => == References == [115] => {{Reflist}} [116] => [117] => == Further reading == [118] => * {{cite book | title=Medical Genetics Summaries | chapter=Voriconazole Therapy and CYP2C19 Genotype | chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK552035/ | veditors=Pratt VM, McLeod HL, Rubinstein WS, Scott SA, Dean LC, Kattman BL, Malheiro AJ | display-editors=3 | publisher=[[National Center for Biotechnology Information]] (NCBI) | date=December 2019 | pmid=31886997 | vauthors=Dean L | url=https://www.ncbi.nlm.nih.gov/books/NBK61999/ }} [119] => [120] => {{Antifungals}} [121] => {{Portal bar|Medicine}} [122] => [123] => [[Category:CYP3A4 inhibitors]] [124] => [[Category:Fluoroarenes]] [125] => [[Category:Lanosterol 14α-demethylase inhibitors]] [126] => [[Category:Organofluorides]] [127] => [[Category:Drugs developed by Pfizer]] [128] => [[Category:Phenylethanolamines]] [129] => [[Category:Pyrimidines]] [130] => [[Category:Wikipedia medicine articles ready to translate]] [131] => [[Category:Tertiary alcohols]] [132] => [[Category:Triazole antifungals]] [133] => [[Category:World Health Organization essential medicines]] [] => )
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Voriconazole

Voriconazole, sold under the brand name Vfend among others, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, candidiasis, coccidioidomycosis, histoplasmosis, penicilliosis, and infections by Scedosporium or Fusarium.

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