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SML2357

Sigma-Aldrich

Isavuconazole

≥98% (HPLC), powder, fungal sterol biosynthesis inhibitor

Synonym(e):

(2R,3R)-3-[4-(4-Cyanophenyl)thiazol-2-yl]-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 1-[(2R,3R)-3-[4-(4-Cyanophenyl)thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-1,2,4-triazole, 4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile, BAL 4815, RO 0094815

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About This Item

Empirische Formel (Hill-System):
C22H17F2N5OS
CAS-Nummer:
241479-67-4
Molekulargewicht:
437.47
MDL-Nummer:
MFCD06407745
UNSPSC-Code:
12352200
NACRES:
NA.77

Produktbezeichnung

Isavuconazole, ≥98% (HPLC)

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

2-8°C

SMILES String

Fc1c(cc(cc1)F)[C@](O)([C@@H](C)c3[s]cc(n3)c4ccc(cc4)C#N)C[n]2ncnc2

InChI

1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1

InChIKey

DDFOUSQFMYRUQK-RCDICMHDSA-N

Anwendung

Isavuconazole has been used as an antifungal agent to test its effect on Mucor circinelloides gene transcription. It has also been used
to analyze its in vitro activity against isolates from the R. argillacea species complex A. fumigatus, N. hiratsukae and C. parapsilosis.

Biochem./physiol. Wirkung

Isavuconazole is a triazole antifungal drug. It inhibits fungal sterol biosynthesis by inhibition of cytochrome P450 sterol 14-α-demethylase (CYP51), an enzyme in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. It has been approved for the treatment of both invasive aspergillosis and invasive mucormycosis.
Triazole antifungal drug.

Piktogramme

Health hazard
GHS08

Signalwort

Warning

H-Sätze

H361fd

Gefahreneinstufungen

Repr. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Analysenzertifikate (COA)

Lot/Batch Number

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Die Dokumentenbibliothek aufrufen

M-P Ledoux et al.
Journal de mycologie medicale, 28(1), 15-22 (2018-03-20)
Isavuconazole, the active moiety of its prodrug isavuconazonium, is a new extended-spectrum triazole whose activity against yeasts, molds, including Aspergillus and mucorales, and dimorphic fungi has been shown in vitro and in preclinical models. The most relevant pharmacokinetics features are
Jeffrey M Rybak et al.
Pharmacotherapy, 35(11), 1037-1051 (2015-11-26)
Coinciding with the continually increasing population of immunocompromised patients worldwide, the incidence of invasive fungal infections has grown over the past 4 decades. Unfortunately, infections caused by both yeasts such as Candida and molds such as Aspergillus or Mucorales remain
Seyedmojtaba Seyedmousavi et al.
Antimicrobial agents and chemotherapy, 59(5), 2855-2866 (2015-03-11)
Azole resistance is an emerging problem in Aspergillus fumigatus which translates into treatment failure. Alternative treatments with new azoles may improve therapeutic outcome in invasive aspergillosis (IA) even for strains with decreased susceptibility to current azoles. The in vivo efficacy

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