Posaconazole

• CAT Number: I002234
• CAS Number: 171228-49-2
• Molecular Formula: C37H42F2N8O4
• Molecular Weight: 700.78
• Purity: ≥95%
• Synonyms: 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
• Target: C14ɑ demethylase
• Solubility: 10 mM in DMSO
• Storage: 3 years -20C powder
• InChI: 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
• InChIKey: RAGOYPUPXAKGKH-XAKZXMRKSA-N
• SMILES: CCC(C(C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5CC(OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F

Posaconazole (CAT: I002234) is a broad-spectrum antifungal medication used to prevent and treat various fungal infections. It belongs to the class of drugs known as triazole antifungals. Posaconazole works by inhibiting the synthesis of ergosterol, an essential component of fungal cell membranes, leading to the disruption of fungal growth and replication. It is effective against a wide range of fungi, including Candida species, Aspergillus species, and certain other molds. It is commonly used in immunocompromised patients, such as those undergoing chemotherapy or hematopoietic stem cell transplantation, to prevent or treat fungal infections.

Overview of Clinical Research

Posaconazole is a 14-alpha demethylase inhibitor and a Cytochrome P 450 enzyme system inhibitor. Phase-II clinical trials started in Invasive bronchopulmonary aspergillosis (In children, In adolescents) in USA, Russia, Peru, Mexico, South Korea, Israel (IV) in 2019.

Reference

1: Uchida K, Yokota N, Yamaguchi H. In vitro antifungal activity of posaconazole against various pathogenic fungi. Int J Antimicrob Agents. 2001 Aug;18(2):167-72. PubMed PMID: 11516940.
2: Petraitiene R, Petraitis V, Groll AH, Sein T, Piscitelli S, Candelario M, Field-Ridley A, Avila N, Bacher J, Walsh TJ. Antifungal activity and pharmacokinetics of posaconazole (SCH 56592) in treatment and prevention of experimental invasive pulmonary aspergillosis: correlation with galactomannan antigenemia. Antimicrob Agents Chemother. 2001 Mar;45(3):857-69. PubMed PMID: 11181372; PubMed Central PMCID: PMC90385.
3: Connolly P, Wheat LJ, Schnizlein-Bick C, Durkin M, Kohler S, Smedema M, Goldberg J, Brizendine E, Loebenberg D. Comparison of a new triazole, posaconazole, with itraconazole and amphotericin B for treatment of histoplasmosis following pulmonary challenge in immunocompromised mice. Antimicrob Agents Chemother. 2000 Oct;44(10):2604-8. PubMed PMID: 10991831; PubMed Central PMCID: PMC90122.
4: Cacciapuoti A, Loebenberg D, Corcoran E, Menzel F Jr, Moss EL Jr, Norris C, Michalski M, Raynor K, Halpern J, Mendrick C, Arnold B, Antonacci B, Parmegiani R, Yarosh-Tomaine T, Miller GH, Hare RS. In vitro and in vivo activities of SCH 56592 (posaconazole), a new triazole antifungal agent, against Aspergillus and Candida. Antimicrob Agents Chemother. 2000 Aug;44(8):2017-22. PubMed PMID: 10898669; PubMed Central PMCID: PMC90007.
5: Molina J, Martins-Filho O, Brener Z, Romanha AJ, Loebenberg D, Urbina JA. Activities of the triazole derivative SCH 56592 (posaconazole) against drug-resistant strains of the protozoan parasite Trypanosoma (Schizotrypanum) cruzi in immunocompetent and immunosuppressed murine hosts. Antimicrob Agents Chemother. 2000 Jan;44(1):150-5. PubMed PMID: 10602737; PubMed Central PMCID: PMC89642.