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SML2357

Sigma-Aldrich

Isavuconazole

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

Synonyme(s) :

(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

Formule empirique (notation de Hill):
C22H17F2N5OS
Numéro CAS:
241479-67-4
Poids moléculaire :
437.47
Numéro MDL:
MFCD06407745
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

product name

Isavuconazole, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

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

Clé InChI

DDFOUSQFMYRUQK-RCDICMHDSA-N

Application

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361fd

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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
A Prigitano et al.
The Journal of hospital infection, 123, 74-79 (2022-02-20)
Preventing and reducing nosocomial infections is a public health goal. Concern about healthcare-associated fungal infections has increased in recent years due to the emergence and spread of new pathogens, increasing antifungal resistance and outbreaks in hospital settings. To investigate the
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
J Steinmann et al.
Antimicrobial agents and chemotherapy, 60(11), 6890-6891 (2016-08-17)
The in vitro susceptibilities to the novel triazole isavuconazole and six other antifungal agents of a large collection of Rasamsonia isolates (n = 47) belonging to seven species were determined. Isavuconazole and voriconazole had no in vitro activity (MIC, >32
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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