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Merck

SML2287

Posaconazole

≥98% (HPLC), lanosterol 14α-demethylase inhibitor, powder

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C37H42F2N8O4
Numéro CAS:
Poids moléculaire :
700.78
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
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Nom du produit

Posaconazole, ≥98% (HPLC)

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

SMILES string

Fc1c(ccc(c1)F)[C@@]3(OC[C@H](C3)COc4ccc(cc4)N5CCN(CC5)c6ccc(cc6)N7C=NN(C7=O)[C@H]([C@@H](O)C)CC)C[n]2ncnc2

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

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.


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Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Harrys A Torres et al.
The Lancet. Infectious diseases, 5(12), 775-785 (2005-11-29)
Posaconazale is a new triazole drug being investigated in phase III clinical trials for the treatment and prevention of invasive fungal infections. In-vitro and in-vivo studies showed that posaconazole has broad-spectrum activity against most Candida species, Cryptococcus neoformans, Aspergillus species
Yanjun Li et al.
Clinical pharmacokinetics, 49(6), 379-396 (2010-05-21)
Posaconazole is a recently approved lipophilic triazole antifungal agent that exhibits potent and broad-spectrum antifungal activity in vitro and in vivo against most Candida spp., Cryptococcus neoformans, Aspergillus spp., many Zygomycetes, endemic fungi and dermatophytes. It has been documented that
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