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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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$221.00
25 MG
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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

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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

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Posaconazole ≥98% (HPLC)

SML2287

Posaconazole

Isavuconazole ≥98% (HPLC)

SML2357

Isavuconazole

Posaconazole VETRANAL®, analytical standard

32103

Posaconazole

Efinaconazole ≥98% (HPLC)

SML1244

Efinaconazole

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

form

powder

form

powder

form

-

form

powder

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

-

solubility

DMSO: 20 mg/mL, clear

color

white to beige

color

white to beige

color

-

color

white to beige

optical activity

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

optical activity

-

optical activity

-

optical activity

[α]/D -85 to -95°, c = 1 in chloroform

Application

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]

Biochem/physiol Actions

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]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    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
    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
    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
    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
    View All Related Papers

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