Voriconazole
White to light yellow solid powder
Others
Voriconazole is a synthetic triazole with antifungal activity. Voriconazole selectively inhibits 14-alpha-lanosterol demethylation in fungi, preventing the production of ergosterol, an essential constituent of the fungal cell membrane, and resulting in fungal cell lysis. (NCI04)
Voriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. Voriconazole therapy is associated with transient, asymptomatic serum aminotransferase elevations and is a known cause of clinically apparent acute drug induced liver injury.
Voriconazole, also known as vfend or VCZ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Voriconazole is a drug which is used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by scedosporium apiospermum and fusarium spp. Voriconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Voriconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, voriconazole is primarily located in the cytoplasm and membrane (predicted from logP). 349.31 g/mol
Voriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. Voriconazole therapy is associated with transient, asymptomatic serum aminotransferase elevations and is a known cause of clinically apparent acute drug induced liver injury.
Voriconazole, also known as vfend or VCZ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Voriconazole is a drug which is used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by scedosporium apiospermum and fusarium spp. Voriconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Voriconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, voriconazole is primarily located in the cytoplasm and membrane (predicted from logP). 349.31 g/mol
Formulation:
349.31 g/mol
Source:
Usage:
Voriconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-286489
CAS Number: 137234-62-9
Molecular Formula: C16H14F3N5O
Molecular Weight: 349.31 g/mol
Purity: ≥ 99%
Inventory: In Stock
| Size | SKU | Price | |
|---|---|---|---|
| 100mg | bt-286489-100mg | $309.08 | |
| 500mg | bt-286489-500mg | $817.54 | |
| 1g | bt-286489-1g | $1,341.85 | |
| 5g | bt-286489-5g | $3,654.00 |
| CAS Number | 137234-62-9 |
|---|---|
| Product Name | Voriconazole |
| Molecular Formula | C16H14F3N5O |
| Molecular Weight | 349.31 g/mol |
| Appearance | White to light yellow solid powder |
| 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 |
| InChI Key | BCEHBSKCWLPMDN-MGPLVRAMSA-N |
| Isomeric SMILES | C[C@@H](C1=NC=NC=C1F)[C@](CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O |
| IUPAC Name | (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol |
| Canonical SMILES | CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O |
| Description | Voriconazole is a synthetic triazole with antifungal activity. Voriconazole selectively inhibits 14-alpha-lanosterol demethylation in fungi, preventing the production of ergosterol, an essential constituent of the fungal cell membrane, and resulting in fungal cell lysis. (NCI04) Voriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. Voriconazole therapy is associated with transient, asymptomatic serum aminotransferase elevations and is a known cause of clinically apparent acute drug induced liver injury. Voriconazole, also known as vfend or VCZ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Voriconazole is a drug which is used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by scedosporium apiospermum and fusarium spp. Voriconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Voriconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, voriconazole is primarily located in the cytoplasm and membrane (predicted from logP). |
| Melting Point | 127-130 °C 127-130°C |
| Other CAS Number | 188416-29-7 137234-62-9 |
| Physical Description | Solid |
| Pictograms | Acute Toxic;Health Hazard;Environmental Hazard |
| Shelf Life | >2 years if stored properly |
| SMILES | CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O |
| Solubility | Soluble in DMSO, not in water |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | UK 109,496 UK 109496 UK-109,496 UK-109496 UK109,496 UK109496 Vfend voriconazole |
| Reference | 1: Turner RB, Martello JL, Malhotra A. Worsening renal function in patients with baseline renal impairment treated with intravenous voriconazole: A systematic review. Int J Antimicrob Agents. 2015 Oct;46(4):362-6. doi: 10.1016/j.ijantimicag.2015.05.023. Epub 2015 Jul 22. Review. PubMed PMID: 26253129. 2: Karthaus M, Lehrnbecher T, Lipp HP, Kluge S, Buchheidt D. Therapeutic drug monitoring in the treatment of invasive aspergillosis with voriconazole in cancer patients--an evidence-based approach. Ann Hematol. 2015 Apr;94(4):547-56. doi: 10.1007/s00277-015-2333-z. Epub 2015 Feb 20. Review. PubMed PMID: 25697592. 3: Gomulka J, Wilson BD, Joyce JC. Toxic epidermal necrolysis due to voriconazole: case report and review. Dermatol Online J. 2014 Sep 16;20(9). pii: 13030/qt2pt32578. Review. PubMed PMID: 25244163. 4: Dolton MJ, McLachlan AJ. Voriconazole pharmacokinetics and exposure-response relationships: assessing the links between exposure, efficacy and toxicity. Int J Antimicrob Agents. 2014 Sep;44(3):183-93. doi: 10.1016/j.ijantimicag.2014.05.019. Epub 2014 Jul 7. Review. PubMed PMID: 25106074. 5: Ho HC, Hsiao SH, Lee CY, Tsai CC. Treatment of refractory Aspergillus otomycosis with voriconazole: case series and review. J Laryngol Otol. 2014 Jun;128(6):547-51. doi: 10.1017/S0022215114001273. Epub 2014 Jun 9. Review. PubMed PMID: 24909800. 6: Jørgensen KJ, Gøtzsche PC, Dalbøge CS, Johansen HK. Voriconazole versus amphotericin B or fluconazole in cancer patients with neutropenia. Cochrane Database Syst Rev. 2014 Feb 24;2:CD004707. doi: 10.1002/14651858.CD004707.pub3. Review. PubMed PMID: 24563222. 7: Owusu Obeng A, Egelund EF, Alsultan A, Peloquin CA, Johnson JA. CYP2C19 polymorphisms and therapeutic drug monitoring of voriconazole: are we ready for clinical implementation of pharmacogenomics? Pharmacotherapy. 2014 Jul;34(7):703-18. doi: 10.1002/phar.1400. Epub 2014 Feb 7. Review. PubMed PMID: 24510446; PubMed Central PMCID: PMC4082739. 8: Williams K, Mansh M, Chin-Hong P, Singer J, Arron ST. Voriconazole-associated cutaneous malignancy: a literature review on photocarcinogenesis in organ transplant recipients. Clin Infect Dis. 2014 Apr;58(7):997-1002. doi: 10.1093/cid/cit940. Epub 2013 Dec 20. Review. PubMed PMID: 24363331. 9: Holle J, Leichsenring M, Meissner PE. Nebulized voriconazole in infections with Scedosporium apiospermum--case report and review of the literature. J Cyst Fibros. 2014 Jul;13(4):400-2. doi: 10.1016/j.jcf.2013.10.014. Epub 2013 Nov 18. Review. PubMed PMID: 24263169. 10: Seyedmousavi S, Mouton JW, Verweij PE, Brüggemann RJ. Therapeutic drug monitoring of voriconazole and posaconazole for invasive aspergillosis. Expert Rev Anti Infect Ther. 2013 Sep;11(9):931-41. doi: 10.1586/14787210.2013.826989. Review. PubMed PMID: 24053274. 11: Tedja R, El-Sherief A, Olbrych T, Gordon S. Multifocal periostitis as a complication of chronic use of voriconazole in a lung transplant recipient. Transpl Infect Dis. 2013 Aug;15(4):424-9. doi: 10.1111/tid.12088. Epub 2013 May 13. Review. PubMed PMID: 23663268. 12: Inano S, Kimura M, Iida J, Arima N. Combination therapy of voriconazole and terbinafine for disseminated fusariosis: case report and literature review. J Infect Chemother. 2013 Dec;19(6):1173-80. doi: 10.1007/s10156-013-0594-9. Epub 2013 Apr 6. Review. PubMed PMID: 23564310. 13: Oliveira Fde M, Unis G, Hochhegger B, Severo LC. Scedosporium apiospermum eumycetoma successfully treated with oral voriconazole: report of a case and review of the Brazilian reports on scedosporiosis. Rev Inst Med Trop Sao Paulo. 2013 Mar-Apr;55(2):121-3. Review. PubMed PMID: 23563766. 14: Sayah DM, Schwartz BS, Kukreja J, Singer JP, Golden JA, Leard LE. Scedosporium prolificans pericarditis and mycotic aortic aneurysm in a lung transplant recipient receiving voriconazole prophylaxis. Transpl Infect Dis. 2013 Apr;15(2):E70-4. doi: 10.1111/tid.12056. Epub 2013 Feb 6. Review. PubMed PMID: 23387799. 15: Rimawi RH, Carter Y, Ware T, Christie J, Siraj D. Use of voriconazole for the treatment of Paecilomyces lilacinus cutaneous infections: case presentation and review of published literature. Mycopathologia. 2013 Apr;175(3-4):345-9. doi: 10.1007/s11046-012-9610-3. Epub 2013 Jan 20. Review. PubMed PMID: 23334554. 16: Davies-Vorbrodt S, Ito JI, Tegtmeier BR, Dadwal SS, Kriengkauykiat J. Voriconazole serum concentrations in obese and overweight immunocompromised patients: a retrospective review. Pharmacotherapy. 2013 Jan;33(1):22-30. doi: 10.1002/phar.1156. Review. PubMed PMID: 23307541. 17: Mikulska M, Novelli A, Aversa F, Cesaro S, de Rosa FG, Girmenia C, Micozzi A, Sanguinetti M, Viscoli C. Voriconazole in clinical practice. J Chemother. 2012 Dec;24(6):311-27. doi: 10.1179/1973947812Y.0000000051. Review. PubMed PMID: 23174096. 18: Cherian T, Giakoustidis A, Yokoyama S, Heneghan M, O'Grady J, Rela M, Wendon J, Heaton DN, Verma A. Treatment of refractory cerebral aspergillosis in a liver transplant recipient with voriconazole: case report and review of the literature. Exp Clin Transplant. 2012 Oct;10(5):482-6. Review. PubMed PMID: 23031086. 19: Watt K, Manzoni P, Cohen-Wolkowiez M, Rizzollo S, Boano E, Jacqz-Aigrain E, Benjamin DK. Triazole use in the nursery: fluconazole, voriconazole, posaconazole, and ravuconazole. Curr Drug Metab. 2013 Feb;14(2):193-202. Review. PubMed PMID: 22935068; PubMed Central PMCID: PMC3541435. 20: Keshtkar-Jahromi M, McTighe AH, Segalman KA, Fothergill AW, Campbell WN. Unusual case of cutaneous and synovial Paecilomyces lilacinus infection of hand successfully treated with voriconazole and review of published literature. Mycopathologia. 2012 Sep;174(3):255-8. doi: 10.1007/s11046-012-9540-0. Epub 2012 Apr 8. Review. PubMed PMID: 22484831. |
| PubChem Compound | Voriconazole |
| Last Modified | Mar 14 2022 |