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SML2287

Sigma-Aldrich

Posaconazole

≥98% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C37H42F2N8O4
Numero CAS:
Peso molecolare:
700.78
Numero MDL:
Codice UNSPSC:
12352200
NACRES:
NA.77

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Saggio

≥98% (HPLC)

Stato

powder

Attività ottica

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

Colore

white to beige

Solubilità

DMSO: 2 mg/mL, clear

Temperatura di conservazione

−20°C

Stringa SMILE

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
RAGOYPUPXAKGKH-XAKZXMRKSA-N

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Applicazioni

Posaconazole has been used:
  • in antifungal susceptibility testing of Aspergillus terreus[1]
  • as a lanosterol 14α-demethylase (CYP51)-specific inhibitor to study its effects on membrane permeability in Candida albicans cells[2]
  • to study its effects on promastigotes[3]

Azioni biochim/fisiol

Posaconazole is a highly potent broadspectrum antifungal agent against the yeast infection caused especially by Candida sp.[4][5] It blocks the growth of fungi by inhibiting the enzyme lanosterol 14α-demethylase (CYP51).[4] 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.[6]

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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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
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
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
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

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