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SML2287

Sigma-Aldrich

Posaconazole

≥98% (HPLC)

Synonym(s):

Posaconazole solution, 2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol, Sch 56592

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About This Item

Empirical Formula (Hill Notation):
C37H42F2N8O4
CAS Number:
171228-49-2
Molecular Weight:
700.78
MDL number:
MFCD00941162
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -24 to -32°, c = 1.0 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1

InChI key

RAGOYPUPXAKGKH-XAKZXMRKSA-N

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Application

Posaconazole has been used:
  • in antifungal susceptibility testing of Aspergillus terreus
  • as a lanosterol 14α-demethylase (CYP51)-specific inhibitor to study its effects on membrane permeability in Candida albicans cells
  • to study its effects on promastigotes

Biochem/physiol Actions

Posaconazole is a highly potent broadspectrum antifungal agent against the yeast infection caused especially by Candida sp. It blocks the growth of fungi by inhibiting the enzyme lanosterol 14α-demethylase (CYP51). In contrast to other antifungal azoles, posaconazole has been reported not to induce the efflux pump mechanism. Posaconazole exhibits antichagasic effects against different strains of Trypanosoma cruzi causing Chagas disease.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chiung-Kuang Chen et al.
PLoS neglected tropical diseases, 4(4), e651-e651 (2010-04-14)
Chagas Disease is the leading cause of heart failure in Latin America. Current drug therapy is limited by issues of both efficacy and severe side effects. Trypansoma cruzi, the protozoan agent of Chagas Disease, is closely related to two other
Galina I Lepesheva et al.
The Journal of biological chemistry, 285(33), 25582-25590 (2010-06-10)
Trypanosoma cruzi causes Chagas disease (American trypanosomiasis), which threatens the lives of millions of people and remains incurable in its chronic stage. The antifungal drug posaconazole that blocks sterol biosynthesis in the parasite is the only compound entering clinical trials
Israel Molina et al.
Current opinion in infectious diseases, 28(5), 397-407 (2015-07-24)
The current therapeutic scenario against Chagas disease has been recently updated with the use of the triazoles in clinical trials and several experimental assays (in-vitro and in-vivo models) which are bringing novel and promising evidence for the treatment of Chagas
Laura Judith Marcos-Zambrano et al.
Antimicrobial agents and chemotherapy, 61(7) (2017-04-26)
The objectives of our study were to describe the characteristics of patients with Candida guilliermondii candidemia and to perform an in-depth microbiological characterization of isolates and compare them with those of patients with C. albicans candidemia. We described the risk
Eleftheria Mavridou et al.
Antimicrobial agents and chemotherapy, 54(2), 860-865 (2009-11-18)
The in vivo efficacy of posaconazole against 4 clinical Aspergillus fumigatus isolates with posaconazole MICs ranging from 0.03 to 16 mg/liter, as determined by CLSI method M38A, was assessed in a nonneutropenic murine model of disseminated aspergillosis. The underlying resistance
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