Posaconazole

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Posaconazole
Clinical data
Trade namesNoxafil, Posanol, others
AHFS/Drugs.comMonograph
MedlinePlusa607036
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow (8 to 47% Oral)
Protein binding98 to 99%
MetabolismLiver (glucuronidation)
Elimination half-life16 to 31 hours
ExcretionFecal (71–77%) and Kidney (13–14%)
Identifiers
  • 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
JSmol)
  • O=C1N(/N=C\N1c2ccc(cc2)N7CCN(c6ccc(OCC3C[C@@](OC3)(c4ccc(F)cc4F)Cn5ncnc5)cc6)CC7)[C@@H](CC)[C@@H](O)C
  • 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 checkY
  • Key:RAGOYPUPXAKGKH-AGDNISCASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Posaconazole, sold under the brand name Noxafil among others, is a

antifungal medication.[7][8]

It was approved for medical use in the United States in September 2006,

generic medication.[10][11]

Medical uses

Posaconazole is used to treat invasive Aspergillus and Candida infections.[5] It is also used for the treatment of oropharyngeal candidiasis (OPC), including OPC refractory to itraconazole and/or fluconazole therapy.[5]

It is also used to treat invasive infections by Candida, Mucor, and Aspergillus species in severely immunocompromised patients.[12][13]

Clinical evidence for its utility in treatment of invasive disease caused by Fusarium species (fusariosis) is limited.[14]

It appears to be helpful in a

mouse model of naegleriasis.[15]

Pharmacology

Pharmacodynamics

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, 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.[5][16][17]

Microbiology

Posaconazole is active against the following microorganisms:[16][18]

Pharmacokinetics

Posaconazole is absorbed within three to five hours. It is predominantly eliminated through the liver, and has a half-life of about 35 hours. Oral administration of posaconazole taken with a high-fat meal exceeds 90% bioavailability and increases the concentration by four times compared to fasting state.[5][18]

References

  1. ^ "Posaconazole (Noxafil) Use During Pregnancy". Drugs.com. 23 April 2019. Archived from the original on 30 January 2020. Retrieved 30 January 2020.
  2. ^ "Posaconazole suspension ARX/Posaconazole TIH/APX-Posaconazole (Arrow Pharma Pty Ltd)". Therapeutic Goods Administration (TGA). 16 February 2023. Archived from the original on 18 March 2023. Retrieved 29 April 2023.
  3. ^ "Posanol Product information". Health Canada. 25 April 2012. Archived from the original on 16 May 2021. Retrieved 3 July 2022.
  4. ^ "Noxafil 100 mg Gastro-resistant Tablets - Summary of Product Characteristics (SmPC)". (emc). 10 January 2022. Archived from the original on 24 February 2022. Retrieved 3 July 2022.
  5. ^ a b c d e f "Noxafil- posaconazole suspension Noxafil- posaconazole tablet, coated Noxafil- posaconazole solution". DailyMed. 20 March 2020. Archived from the original on 26 February 2021. Retrieved 15 August 2020.
  6. ^ "Noxafil EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 19 October 2021. Retrieved 3 July 2022.
  7. PMID 18035188
    .
  8. S2CID 21777822. Retrieved 11 December 2008.[dead link
    ]
  9. ^ "Drug Approval Package: Noxafil (Posaconazole) NDA #022003". U.S. Food and Drug Administration (FDA). 9 November 2006. Archived from the original on 3 April 2021. Retrieved 15 August 2020.
  10. ^ "Posaconazole: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 20 October 2020. Retrieved 15 August 2020.
  11. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration. 17 October 2022. Archived from the original on 26 January 2021. Retrieved 28 November 2022.
  12. PMID 14657086
    .
  13. PMID 17143808.  – via JSTOR
    (subscription required)
  14. PMID 16619151
    .
  15. PMID 30358879
    .
  16. ^
    ISBN 978-0-07-142280-2
  17. ^ "Clinical Pharmacology Posaconazole". Archived from the original on 30 August 2021. Retrieved 18 February 2010.
  18. ^ a b Ashley ED, Perfect JR (October 2017). "Pharmacology of azoles". In Kauffman CA (ed.). UpToDate. Waltham, MA: UpToDate. Archived from the original on 9 February 2013. Retrieved 18 February 2010.

External links

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