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Posaconazole
Systematic (IUPAC) name
4-(4-(4-(4-(((3r,5r)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-((2s,3s)-2-hydroxypentan-3-yl)-1,2,4-triazol-3-one
Identifiers
CAS number 171228-49-2
ATC code J02AC04
PubChem 147912
Chemical data
Formula C 37H42F2N8O4  
Mol. mass 700.778 g/mol
Synonyms 4-{4-[4-(4-{[(5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-[(2 S,3S)-2-hydroxypentan-3-yl]-4,5-dihydro-1H-1,2,4-triazol-5-one
Pharmacokinetic data
Bioavailability High
Protein binding 98 to 99%
Metabolism Hepatic glucuronidation
Half life 16 to 31 hours
Excretion Fecal (77%) and renal (14%)
Therapeutic considerations
Licence data

EU EMEA:linkUS FDA:link

Pregnancy cat. B3(AU) C(US)
Legal status -only (US)
Routes Oral
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Posaconazole is a triazole antifungal drug.[1][2]

Posaconazole is marketed in the United States, the European Union, and in other countries by Schering-Plough under the trade name Noxafil.

Uses

It is used to treat invasive infections by Candida species[3], Mucor, and Aspergillus species[4] in severely immunocompromised patients.

There is also limited clinical evidence for its utility in treatment of invasive disease caused by Fusarium species (fusariosis).[5]

Two studies published in the January 25, 2007 issue of the New England Journal of Medicine suggest posaconazole may be superior to other triazoles, such as fluconazole or itraconazole, in the prevention of invasive fungal infections, although it may cause more serious side effects.[6][7]

References

  1. ^ Schiller DS, Fung HB (September 2007). "Posaconazole: an extended-spectrum triazole antifungal agent". Clin Ther 29 (9): 1862–86. doi:10.1016/j.clinthera.2007.09.015. PMID 18035188. http://linkinghub.elsevier.com/retrieve/pii/S0149-2918(07)00296-2.  
  2. ^ Rachwalski EJ, Wieczorkiewicz JT, Scheetz MH (October 2008). "Posaconazole: an oral triazole with an extended spectrum of activity". Ann Pharmacother 42 (10): 1429–38. doi:10.1345/aph.1L005. PMID 18713852. http://www.theannals.com/cgi/pmidlookup?view=long&pmid=18713852.  
  3. ^ Li X, Brown N, Chau AS, et al. (January 2004). "Changes in susceptibility to posaconazole in clinical isolates of Candida albicans". J. Antimicrob. Chemother. 53 (1): 74–80. doi:10.1093/jac/dkh027. PMID 14657086. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=14657086.  
  4. ^ Walsh TJ, Raad I, Patterson TF, et al. (January 2007). "Treatment of invasive aspergillosis with posaconazole in patients who are refractory to or intolerant of conventional therapy: an externally controlled trial". Clin. Infect. Dis. 44 (1): 2–12. doi:10.1086/508774. PMID 17143808. http://www.journals.uchicago.edu/doi/abs/10.1086/508774?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dncbi.nlm.nih.gov.  
  5. ^ Raad I, Hachem R, Herbrecht R, et al. (2006). "Posaconazole as salvage treatment for invasive fusariosis in patients with underlying hematologic malignancy and other conditions" (). Clin Infect Dis 42 (10): 1398–1403. http://www.journals.uchicago.edu/CID/journal/issues/v42n10/38411/brief/38411.abstract.html.  
  6. ^ Cornely O, Maertens J, Winston D, Perfect J, Ullmann A, Walsh T, Helfgott D, Holowiecki J, Stockelberg D, Goh Y, Petrini M, Hardalo C, Suresh R, Angulo-Gonzalez D (2007). "Posaconazole vs. fluconazole or itraconazole prophylaxis in patients with neutropenia". N Engl J Med 356 (4): 348–59. doi:10.1056/NEJMoa061094. PMID 17251531.  
  7. ^ Ullmann A, Lipton J, Vesole D, Chandrasekar P, Langston A, Tarantolo S, Greinix H, Morais de Azevedo W, Reddy V, Boparai N, Pedicone L, Patino H, Durrant S (2007). "Posaconazole or fluconazole for prophylaxis in severe graft-versus-host disease". N Engl J Med 356 (4): 335–47. doi:10.1056/NEJMoa061098. PMID 17251530.  
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