7602. Posaconazole

Nomenclature

CAS number: 171228-49-2
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; (3R-cis)-4-[4-[4-[4-[5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)tetrahydrofuran-3-ylmethoxy]phenyl]piperazin-1-yl]phenyl]-2-[1(S)-ethyl-2(S)-hydroxypropyl]-3,4-dihydro-2H-1,2,4-triazol-3-one; Sch-56592; Noxafil (Schering-Plough).
C37H42F2N8O4; mol wt 700.78.
C 63.41%, H 6.04%, F 5.42%, N 15.99%, O 9.13%.

Description and references

Orally active triazole antifungal. Prepn: A. K. Saksena et al., WO 9517407; eidem, US 5661151 (1995, 1997 both to Schering); eidem, Tetrahedron Lett. 37, 5657 (1996). Comparative antifungal spectrum: A. Cacciapuoti et al., Antimicrob. Agents Chemother. 44, 2017 (2000). Pharmacokinetics, safety and tolerability: R. Courtney et al., ibid. 47, 2788 (2003). HPLC determn in serum: H. Kim et al., J. Chromatogr. B 738, 93 (2000). Review of development: A. K. Saksena et al. in Anti-Infectives: Recent Advances in Chemistry and Structure Activity Relationships (Royal Soc. Chem., Cambridge, 1997) pp 180-199; and clinical efficacy in fungal infections: R. Herbrecht, Int. J. Clin. Pract. 58, 612-624 (2004).

Chemical structure

Properties

White solid, mp 170-172°.

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic); Triazoles