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Posaconazole
- SCH 56592 - Noxafil
- Optical Purity: Optically pure
- Soluble in DMSO
- MF: C37H42F2N8O4
- MW: 700.78
Description
Posaconazole (SCH56592) is a broad-spectrum triazole antifungal compound that inhibits fungal lanosterol 14-alpha demethylase (CYP51).
CYP51 inhibition disrupts ergosterol biosynthesis and compromises fungal membrane integrity. Posaconazole is useful as a reference azole for antifungal susceptibility testing, CYP51 pharmacology and studies of azole resistance mechanisms.
Key Features
- Triazole inhibitor of fungal CYP51
- Blocks ergosterol biosynthesis
- Broad-spectrum antifungal pharmacology
- Reference compound for azole-resistance research
Applications
- Antifungal susceptibility studies
- CYP51 enzyme pharmacology
- Ergosterol biosynthesis assays
- Fungal resistance mechanism research
More Information
| Parent CAS No. | 171228-49-2 |
|---|---|
| Chemical Name | 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-hydroxypentan-3-yl)-1H-1,2,4-triazol-5(4H)-one |
| SMILES | C1(=O)N(C2C=CC(N3CCN(C4C=CC(OC[C@@H]5CO[C@@](CN6N=CN=C6)(C6C(F)=CC(F)=CC=6)C5)=CC=4)CC3)=CC=2)C=NN1[C@H]([C@@H](O)C)CC |&1:17,20,45,46,r| |
| MFCD | N.A. |
| 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 |
| CID | 468595 |
| Short Description | Antifungal agent |
References
- JA Urbina et al. Antiproliferative Effects and Mechanism of Action of SCH 56592 against Trypanosoma (Schizotrypanum)cruzi: In Vitro and In Vivo Studies. Antimicrob. Agents Chemother. 1998, 42(7), 1771-1777.
- DS Schiller and HB Fung. Posaconazole: an extended-spectrum triazole antifungal agent. Clin Ther 2007, 29(9), 1862–86.
- EJ Rachwalski et al. Posaconazole: an oral triazole with an extended spectrum of activity. Ann Pharmacother 2008, 42 (10): 1429–38.
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