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MedKoo Cat#: 145013 | Name: Voriconazole, (R,R)-

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Voriconazole is an important agent in the antifungal armamentarium. Voriconazole is a triazole antifungal indicated for invasive fungal infections that exhibits a high degree of inter-individual and intra-individual pharmacokinetic variability. Voriconazole is an antifungal drug used for the treatment of invasive fungal infections.

Chemical Structure

Voriconazole, (R,R)-
Voriconazole, (R,R)-
CAS#239807-03-5

Theoretical Analysis

MedKoo Cat#: 145013

Name: Voriconazole, (R,R)-

CAS#: 239807-03-5

Chemical Formula: C16H14F3N5O

Exact Mass: 349.1150

Molecular Weight: 349.32

Elemental Analysis: C, 55.01; H, 4.04; F, 16.32; N, 20.05; O, 4.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Voriconazole, (R,R)-;
IUPAC/Chemical Name
(2R,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
InChi Key
BCEHBSKCWLPMDN-QLJPJBMISA-N
InChi Code
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-/m1/s1
SMILES Code
C[C@H](C1=NC=NC=C1F)[C@](O)(CN2C=NC=N2)C3=C(F)C=C(F)C=C3
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 349.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Maertens JA, Raad II, Marr KA, Patterson TF, Kontoyiannis DP, Cornely OA, Bow EJ, Rahav G, Neofytos D, Aoun M, Baddley JW, Giladi M, Heinz WJ, Herbrecht R, Hope W, Karthaus M, Lee DG, Lortholary O, Morrison VA, Oren I, Selleslag D, Shoham S, Thompson GR 3rd, Lee M, Maher RM, Schmitt-Hoffmann AH, Zeiher B, Ullmann AJ. Isavuconazole versus voriconazole for primary treatment of invasive mould disease caused by Aspergillus and other filamentous fungi (SECURE): a phase 3, randomised-controlled, non-inferiority trial. Lancet. 2016 Feb 20;387(10020):760-9. doi: 10.1016/S0140-6736(15)01159-9. Epub 2015 Dec 10. PMID: 26684607. 2: Tan I, Lomasney L, Stacy GS, Lazarus M, Mar WA. Spectrum of Voriconazole- Induced Periostitis With Review of the Differential Diagnosis. AJR Am J Roentgenol. 2019 Jan;212(1):157-165. doi: 10.2214/AJR.18.19991. Epub 2018 Nov 7. PMID: 30403528. 3: Malani AN, Kerr LE, Kauffman CA. Voriconazole: How to Use This Antifungal Agent and What to Expect. Semin Respir Crit Care Med. 2015 Oct;36(5):786-95. doi: 10.1055/s-0035-1562903. Epub 2015 Sep 23. PMID: 26398543. 4: Boglione-Kerrien C, Zerrouki S, Le Bot A, Camus C, Marchand T, Bellissant E, Tron C, Verdier MC, Gangneux JP, Lemaitre F. Can we predict the influence of inflammation on voriconazole exposure? An overview. J Antimicrob Chemother. 2023 Nov 6;78(11):2630-2636. doi: 10.1093/jac/dkad293. PMID: 37796931. 5: Jakobsen DM, Justad BA, Helweg-Larsen J, Katzenstein TL. [Voriconazole- induced periostitis]. Ugeskr Laeger. 2019 Apr 29;181(18):V12180870. Danish. PMID: 31036146. 6: Marks DI, Liu Q, Slavin M. Voriconazole for prophylaxis of invasive fungal infections after allogeneic hematopoietic stem cell transplantation. Expert Rev Anti Infect Ther. 2017 May;15(5):493-502. doi: 10.1080/14787210.2017.1305886. Epub 2017 Mar 24. PMID: 28335642. 7: Li X, Lai F, Jiang Z, Li M, Chen Z, Cheng J, Cui H, Wen F. Effects of inflammation on voriconazole levels: A systematic review. Br J Clin Pharmacol. 2022 Dec;88(12):5166-5182. doi: 10.1111/bcp.15495. Epub 2022 Aug 25. PMID: 35973037. 8: Greene JP 2nd, Trotter K. Voriconazole-Induced Periostitis in a Transplant Patient. J Clin Rheumatol. 2022 Apr 1;28(3):e671. doi: 10.1097/RHU.0000000000001850. PMID: 35325905. 9: Rosanova MT, Bes D, Serrano Aguilar P, Sberna N, Lede R. Efficacy and safety of voriconazole in immunocompromised patients: systematic review and meta- analysis. Infect Dis (Lond). 2018 Jul;50(7):489-494. doi: 10.1080/23744235.2017.1418531. Epub 2017 Dec 20. PMID: 29262742. 10: Schulz J, Kluwe F, Mikus G, Michelet R, Kloft C. Novel insights into the complex pharmacokinetics of voriconazole: a review of its metabolism. Drug Metab Rev. 2019 Aug;51(3):247-265. doi: 10.1080/03602532.2019.1632888. Epub 2019 Aug 16. PMID: 31215810. 11: Hanai Y, Hamada Y, Kimura T, Matsumoto K, Takahashi Y, Fujii S, Nishizawa K, Takesue Y. Optimal trough concentration of voriconazole with therapeutic drug monitoring in children: A systematic review and meta-analysis. J Infect Chemother. 2021 Feb;27(2):151-160. doi: 10.1016/j.jiac.2020.11.014. Epub 2020 Dec 26. PMID: 33376032. 12: van den Born DA, Märtson AG, Veringa A, Punt NC, van der Werf TS, Alffenaar JC, Sturkenboom MGG, Touw DJ. Voriconazole exposure is influenced by inflammation: A population pharmacokinetic model. Int J Antimicrob Agents. 2023 Apr;61(4):106750. doi: 10.1016/j.ijantimicag.2023.106750. Epub 2023 Feb 8. PMID: 36758777. 13: Lewis JS 2nd, Wiederhold NP, Hakki M, Thompson GR 3rd. New Perspectives on Antimicrobial Agents: Isavuconazole. Antimicrob Agents Chemother. 2022 Sep 20;66(9):e0017722. doi: 10.1128/aac.00177-22. Epub 2022 Aug 15. PMID: 35969068; PMCID: PMC9487460. 14: Zhong X, Tong X, Ju Y, Du X, Li Y. Interpersonal Factors in the Pharmacokinetics and Pharmacodynamics of Voriconazole: Are CYP2C19 Genotypes Enough for Us to Make a Clinical Decision? Curr Drug Metab. 2018;19(14):1152-1158. doi: 10.2174/1389200219666171227200547. PMID: 29361899; PMCID: PMC6635675. 15: Kadam RS, Van Den Anker JN. Pediatric Clinical Pharmacology of Voriconazole: Role of Pharmacokinetic/Pharmacodynamic Modeling in Pharmacotherapy. Clin Pharmacokinet. 2016 Sep;55(9):1031-43. doi: 10.1007/s40262-016-0379-2. PMID: 26979736. 16: Shen J, Wang B, Wang S, Chen F, Meng D, Jiang H, Zhou Y, Geng P, Zhou Q, Liu B. Effects of Voriconazole on the Pharmacokinetics of Vonoprazan in Rats. Drug Des Devel Ther. 2020 Jun 4;14:2199-2206. doi: 10.2147/DDDT.S255427. PMID: 32581516; PMCID: PMC7280087. 17: Ghobadi E, Saednia S, Emami S. Synthetic approaches and structural diversity of triazolylbutanols derived from voriconazole in the antifungal drug development. Eur J Med Chem. 2022 Mar 5;231:114161. doi: 10.1016/j.ejmech.2022.114161. Epub 2022 Jan 29. PMID: 35134679. 18: 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. PMID: 25106074. 19: Ito H, Ogawa R. Itraconazole and Voriconazole: The Complexity of Dose Adjustments. Clin Infect Dis. 2022 Aug 31;75(3):552. doi: 10.1093/cid/ciac064. PMID: 35092680. 20: Sharma N, Bagga B, Singhal D, Nagpal R, Kate A, Saluja G, Maharana PK. Fungal keratitis: A review of clinical presentations, treatment strategies and outcomes. Ocul Surf. 2022 Apr;24:22-30. doi: 10.1016/j.jtos.2021.12.001. Epub 2021 Dec 13. PMID: 34915188.

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