SML2287

Posaconazole

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

• Synonym(e): 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
• Empirische Formel (Hill-System): C₃₇H₄₂F₂N₈O₄
• CAS-Nummer: 171228-49-2
• Molekulargewicht: 700.78
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00941162
• Assay: ≥98% (HPLC)
• Form: powder

Eigenschaften

• Produktname: 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

Beschreibung

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.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• Was ist los?: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable