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Posaconazole
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Systematic (IUPAC) name
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4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro- 5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy] phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl- 2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
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Identifiers
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CAS number
| 171228-49-2
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ATC code
| J02AC04
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PubChem
| 147912
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Chemical data
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Formula | C37H42F2N8O4
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Mol. mass | 700.778 g/mol
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Pharmacokinetic data
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Bioavailability | High
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Protein binding
| 98 to 99%
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Metabolism | Hepatic glucuronidation
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Half life | 16 to 31 hours
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Excretion | Fecal (77%) and renal (14%)
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Therapeutic considerations
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Licence data |
EU US
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Pregnancy cat.
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B3(AU) C(US)
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Legal status
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℞-only(US)
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Routes
| Oral
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Posaconazole is a triazole antifungal drug that is used to treat invasive infections by Candida species and Aspergillus species in severely immunocompromised patients. There is also limited clinical evidence for its utility in treatment of invasive disease caused by Fusarium species (fusariosis).[1] 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.[2][3]
Additional recommended knowledge
Posaconazole is marketed in the U.S. by Schering-Plough under the trade name Noxafil.
References
- ^ 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.
- ^ 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. PMID 17251531.
- ^ 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. PMID 17251530.
Antifungals (D01 and J02) |
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Antibiotics | Griseofulvin • polyene antimycotics (Natamycin, Nystatin) |
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Topical azoles | imidazoles (Bifonazole, Clomidazole, Clotrimazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole) • triazoles (Fluconazole) • benzimidazole (Thiabendazole) |
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Other topicals | Ciclopirox • Ethylparaben • Flucytosine • Salicylic acid • Selenium sulfide • Tolnaftate • Undecylenic acid • allylamines (Amorolfine, Butenafine, Naftifine, Terbinafine) |
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For systemic use | Griseofulvin • allylamine (Terbinafine) • polyene antimycotic (Amphotericin B) • triazoles (Itraconazole, Posaconazole, Voriconazole) • echinocandins (Anidulafungin, Caspofungin, Micafungin) |
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Other | Tea tree oil • citronella oil • lemon grass • orange oil • patchouli • lemon myrtle |
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Can cause very severe kidney problems in otherwise healthy young individuals within days of starting course.
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