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SML2357

Sigma-Aldrich

Isavuconazole

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

Synonym(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

Empirical Formula (Hill Notation):
C22H17F2N5OS
CAS Number:
241479-67-4
Molecular Weight:
437.47
MDL number:
MFCD06407745
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Isavuconazole, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

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

InChI key

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.

Biochem/physiol Actions

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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000370819
0000352642
0000354449
0000327988
0000327989

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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
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
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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