Voriconazole

  • CAT Number: A000786
  • CAS Number: 137234-62-9
  • Molecular Formula: C16H14F3N5O
  • Molecular Weight: 349.3
  • Purity: ≥95%
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Voriconazole is a triazole antifungal medication that is generally used to treat serious, invasive fungal infections. Voriconazole has also been proven effective against a number of other serious fungal pathogens. This includes infections by Fusarium spp and Scedosporium apiospermum (asexual form of Pseudallescheria boydii). Although infrequently seen, these molds are emerging as more common and deadly causes of fungal infection in seriously immunocompromised patients, and the development of voriconazole has been an important advance in their treatment as they are generally resistant to other antifungal agents (including amphotericin B). Voriconazole is the first and only drug ever specifically indicated for their treatment by the FDA. Voriconazole has also been used to treat severe fungal corneal infection.

Catalog Number A000786
CAS Number 137234-62-9
Synonyms

137234-62-9; Vfend; UK-109496; (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; Voriconazol

Molecular Formula

C16H14F3N5O

Purity 95%
Target CYP3A/CYP450
Solubility >17.5mg/mL in DMSO
Storage -20°C
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
InChIKey BCEHBSKCWLPMDN-MGPLVRAMSA-N
SMILES CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
Reference

1: Kaneko Y, Kageyama R, Hashizume H. Agranulocytosis associated with
voriconazole-induced hypersensitivity syndrome. J Dermatol. 2017 Nov 23. doi:
10.1111/1346-8138.14142. [Epub ahead of print] PubMed PMID: 29168223.
<br>

2: Foolad F, Kontoyiannis DP. Persistent CNS toxicity in a patient receiving
posaconazole tablets after discontinuation of voriconazole due to
supratherapeutic serum levels. J Antimicrob Chemother. 2017 Oct 7. doi:
10.1093/jac/dkx362. [Epub ahead of print] PubMed PMID: 29121264.
<br>

3: Ruban VV, Archana PT, Sundararajan M, Geraldine P, Thomas PA. Inflammation and
oxidative stress in corneal tissue in experimental keratitis due to Fusarium
solani: Amelioration following topical therapy with voriconazole and
epigallocatechin gallate. Mycoses. 2017 Oct 24. doi: 10.1111/myc.12718. [Epub
ahead of print] PubMed PMID: 29064157.
<br>

4: Liu X, Su H, Tong J, Chen J, Yang H, Xiao L, Hu J, Zhang L. Significance of
monitoring plasma concentration of voriconazole in a patient with liver failure:
A case report. Medicine (Baltimore). 2017 Oct;96(42):e8039. doi:
10.1097/MD.0000000000008039. PubMed PMID: 29049191; PubMed Central PMCID:
PMC5662357.
<br>

5: Lee KH, Lim YT, Hah JO, Kim YK, Lee CH, Lee JM. Voriconazole plus caspofungin
for treatment of invasive fungal infection in children with acute leukemia. Blood
Res. 2017 Sep;52(3):167-173. doi: 10.5045/br.2017.52.3.167. Epub 2017 Sep 25.
PubMed PMID: 29043231; PubMed Central PMCID: PMC5641508.

<br>
6: Gastine S, Lehrnbecher T, Müller C, Farowski F, Bader P, Ullmann-Moskovits J,
Cornely OA, Groll AH, Hempel G. Pharmacokinetic Modelling of Voriconazole to
Develop an Alternative Dosing Regimen in Children. Antimicrob Agents Chemother.
2017 Oct 16. pii: AAC.01194-17. doi: 10.1128/AAC.01194-17. [Epub ahead of print]
PubMed PMID: 29038273.
<br>

7: Criado PR, Cosenza FD, Junior WB, Ferreira PS. Longitudinal melanonychia due
to voriconazole therapy during treatment of chromoblastomycosis. Clin Exp
Dermatol. 2017 Oct 13. doi: 10.1111/ced.13279. [Epub ahead of print] PubMed PMID:
29030858.
<br>

8: Ebrahimpour S, Namazi S, Mohammadi M, Nikbakht M, Hadjibabaie M, Masoumi HT,
Ghavamzadeh A. Impact of CYP2C19 Polymorphisms on Serum Concentration of
Voriconazole in Iranian Hematological Patients. J Res Pharm Pract. 2017
Jul-Sep;6(3):151-157. doi: 10.4103/jrpp.JRPP_17_31. PubMed PMID: 29026840; PubMed
Central PMCID: PMC5632935.
<br>

9: Tian B, Yan Q, Wang J, Ding C, Sai S. Enhanced antifungal activity of
voriconazole-loaded nanostructured lipid carriers against Candida albicans with a
dimorphic switching model. Int J Nanomedicine. 2017 Sep 26;12:7131-7141. doi:
10.2147/IJN.S145695. eCollection 2017. PubMed PMID: 29026306; PubMed Central
PMCID: PMC5627732.

<br>
10: Girmenia C, Annino L, Bertaina A, Mariotti B, Caselli D, Fanci R, Barberi W,
Marchesi F, Carotti A, Ferrari A, Cerchiara E, Cupelli L, Arcioni F, Ribersani M,
Proia A, Cartoni C, Girardi K, Venditti A, Cassetta MI, Fallani S, Novelli A.
Voriconazole treatment in adults and children with hematological diseases: can it
be used without measurement of plasma concentration? Med Mycol. 2017 Aug 2. doi:
10.1093/mmy/myx053. [Epub ahead of print] PubMed PMID: 28992093.

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