Posaconazole

Overview

Posaconazole, sold under the brand name Noxafil among others, is a triazole antifungal medication.[1][2] WP

It was approved for medical use in the European Union in October 2005, and in the United States in September 2006. It is available as a generic medication.[3–7] WP

Uses, dosage and effects

Medical uses

Posaconazole is used to treat invasive Aspergillus and Candida infections. It is also used for the treatment of oropharyngeal candidiasis (OPC), including OPC refractory to other drugs such as itraconazole and fluconazole.[4] WP

Clinical evidence of efficacy in treatment of invasive disease caused by Fusarium species (fusariosis) is limited.[8] WP

Intravenous administration appears to be helpful in a mouse model of naegleriasis and the drug kills Acanthamoeba castellanii cysts in vitro.[9][10] WP

It has been used to treat mucormycosis (black fungus disease) caused by Rhizopus mold.[11] WP

Pharmacology

Mechanism of action

Posaconazole works by disrupting the functions of certain fungal and protozoal membrane-bound enzyme systems. It does this by blocking the synthesis and turnover of the eukaryotic cell membrane component ergosterol via the inhibition of an enzyme known as CYP51. Posaconazole is significantly more potent at binding to CYP51 than itraconazole.[4][12][13] WP

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.[4][14] WP

Chemistry

Formula

C37H42F2N8O4 PC

CAS number

171228-49-2 PC

Molar mass (g/mol)

700.8 PC

IUPAC name (computed by PubChem)

4-[4-[4-[4-[[(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 PC

SMILES

CC[C@@H]([C@H](C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5C[C@](OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F PC

InChIKey

RAGOYPUPXAKGKH-AGDNISCASA-N PC

PubChem CID

147912

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Schiller DS, Fung HB. Posaconazole: an extended-spectrum triazole antifungal agent. Clinical Therapeutics. September 2007. doi:10.1016/j.clinthera.2007.09.015 · PMID 18035188
2. Journal / agency Rachwalski EJ, Wieczorkiewicz JT, Scheetz MH. Posaconazole: an oral triazole with an extended spectrum of activity. The Annals of Pharmacotherapy. October 2008. doi:10.1345/aph.1L005 · PMID 18713852
3. Journal / agency Noxafil EPAR. 28 March 2007
4. Journal / agency Noxafil- posaconazole suspension Noxafil- posaconazole tablet, coated Noxafil- posaconazole solution. 20 March 2020
5. Journal / agency Drug Approval Package: Noxafil (Posaconazole) NDA #022003. 9 November 2006
6. Journal / agency Posaconazole: FDA-Approved Drugs
7. Journal / agency First Generic Drug Approvals. 17 October 2022
8. Journal / agency Raad II, Hachem RY, Herbrecht R, Graybill JR, Hare R, Corcoran G, Kontoyiannis DP. Posaconazole as salvage treatment for invasive fusariosis in patients with underlying hematologic malignancy and other conditions. Clinical Infectious Diseases. May 2006. doi:10.1086/503425 · PMID 16619151
9. Journal / agency Colon BL, Rice CA, Guy RK, Kyle DE. Phenotypic Screens Reveal Posaconazole as a Rapidly Acting Amebicidal Combination Partner for Treatment of Primary Amoebic Meningoencephalitis. The Journal of Infectious Diseases. March 2019. doi:10.1093/infdis/jiy622 · PMID 30358879 · PMC6420171
10. Journal / agency Iovieno A, Miller D, Ledee DR, Alfonso EC. Cysticidal activity of antifungals against different genotypes of Acanthamoeba. Antimicrob Agents Chemother. September 2014. doi:10.1128/AAC.02635-14 · PMID 25001304 · PMC4135811
11. Journal / agency Fatemizadeh R, Rodman E, Demmler-Harrison GJ, Dinu D. Rhizopus Infection in a Preterm Infant: A Novel Use of Posaconazole. Pediatr Infect Dis J. April 2020. doi:10.1097/INF.0000000000002554 · PMID 32084112
12. Other Brunton L, Lazo J, Parker K. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. San Francisco: McGraw-Hill; 2006 ISBN 978-0-07-142280-2
13. Other Clinical Pharmacology Posaconazole
14. Other Ashley ED, Perfect JR. UpToDate. October 2017

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.