Posaconazole

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Posaconazole
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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
Clinical data
[[Regulation of therapeutic goods |Template:Engvar data]]
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
administration		 Oral
Legal status
Legal status
Pharmacokinetic data
Bioavailability High
Protein binding 98 to 99%
Metabolism Hepatic glucuronidation
Biological half-life 16 to 31 hours
Excretion Fecal (77%) and renal (14%)
Identifiers
CAS Number 171228-49-2
ATC code J02AC04 (WHO)
PubChem CID 147912
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-[(2S,3S)-2-hydroxypentan-3-yl]-4,5-dihydro-1H-1,2,4-triazol-5-one
Chemical data
Formula C37H42F2N8O4
Molar mass 700.778 g/mol[[Script error: No such module "String".]]
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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. In Canada, posaconazole is marketed by Schering-Plough under the trade name Posanol.

Pharmacology

Mode of action

Posaconazole works by disrupting the close packing of acyl chains of phospholipids, impairing the functions of certain membrane-bound enzyme systems such as ATPase and enzymes of the electron transport system and thus inhibiting growth of the fungi. It does this by blocking the synthesis of ergosterol by inhibiting of the enzyme lanosterol 14α-demethylase and accumulation of methylated sterol precursors. Posaconazole is significantly more potent at inhibiting 14-alpha demethylase than itraconazole.[3][4][5]

Microbiology

Posaconazole is active against the following microorganisms:[3][6]

Pharmacokinetics

Posaconazole is absorbed within 3-5 hours. Posaconazole is predominately eliminated through the liver and has a half life of about 35 hours. Oral administration of Posconazole taken with a high fat meal exceeds 90% bioavailability and increases the concentration by 4 times compared to fasting state.[6][7]

Clinical use

It is used to treat invasive infections by Candida species[8], Mucor, and Aspergillus species[9] in severely immunocompromised patients.

There is also limited clinical evidence for its utility in treatment of invasive disease caused by Fusarium species (fusariosis).[10]

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.[11][12]

References

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Wall/
membrane
Ergosterol
inhibitors
topical: Thiabendazole
topical: (Natamycin, Nystatin#)
systemic: (Amphotericin B#)
Intracellular
Others

M: MYC

drug (fung)


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  1. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  2. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  3. ↑ 3.0 3.1 Brunton L, Lazo J, Parker K. Goodman and Gilman’s The Pharmacological Basis of Therapeutics. 11th ed. San Francisco: McGraw-Hill; 2006. ISBN 0071422803
  4. ↑ "Clinical Pharmacology Pasoconazole". Retrieved 18 February 2010. 
  5. ↑ "Daily Med, Product Information Noxafil". Retrieved 18 February 2010. 
  6. ↑ 6.0 6.1 Dodds Ashley, Elizabeth; Perfect, John (October 13, 2009). "Pharmacology of azoles". Retrieved 18 February 2010. 
  7. ↑ "Drugs at FDA: Noxafil" (PDF). Retrieved 18 February 2010. 
  8. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  9. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  10. ↑ 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" ([dead link]). Clin Infect Dis. 42 (10): 1398–1403.  External link in |journal= (help)
  11. ↑ 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. 
  12. ↑ 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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