SML2287

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

Properties

• 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

Description

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]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable