Posaconazole

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Cat Number

API171228492

CAS Number

171228-49-2

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CAS Number

171228-49-2

EINECS

682-747-8

Storage

Store at room temperature

Synonyms

Noxafil; SCH56592; posaconazol

Molecular Formula

C37H42F2N8O4

Molecular Weight

700.8

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)OC[C@H]5C[C@](OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F

Appearance

White solid

Melting Point

170-172°C

Boiling Point

850.7±75.0°C at 760 mmHg (Predicted)

Relative Density

1.36±0.1 (Predicted)

General Description

Posaconazole is a synthetic triazole antifungal agent with a large lipophilic side chain, structurally related to itraconazole. Its chemical structure is 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-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,2,4-triazol-3-one.

Mechanism of Action

Posaconazole inhibits the synthesis of ergosterol by blocking the enzyme lanosterol 14α-demethylase, which is essential for the fungal cell membrane. This leads to the accumulation of toxic sterols and disruption of membrane integrity. The drug has a broad spectrum of activity, including against Aspergillus, Candida, and Zygomycetes species.

Application

Posaconazole is indicated for the prophylaxis of invasive fungal infections in patients with severe immunosuppression, such as those with hematologic malignancies or undergoing hematopoietic stem cell transplantation. It is also used for the treatment of oropharyngeal candidiasis and for the treatment of invasive aspergillosis in patients refractory to other azoles. The drug is effective in reducing the incidence of fungal infections.

Differentiated HL‑60 cells loaded with posaconazole achieved intracellular concentrations 265‑fold higher than extracellular, maintained chemotaxis, and transferred the drug to Aspergillus hyphae in a contact‑dependent manner, reducing fungal viability. In a neutropenic mouse model of invasive pulmonary aspergillosis, posaconazole‑loaded cells significantly reduced fungal burden. This leukocyte‑loading strategy may improve antifungal delivery and holds promise for therapy.

Fig. 1 Posaconazole-loaded dHL-60 cell mediated inhibition of Aspergillus fumigatus. (Baistrocchi SR, et al., 2017)

References

Baistrocchi SR, et al. Posaconazole-Loaded Leukocytes as a Novel Treatment Strategy Targeting Invasive Pulmonary Aspergillosis. J Infect Dis. 2017;215(11):1734-1741.

Posaconazole was conjugated to PEG-imidazole modified generation 5 dendrimers, achieving an average of 23 drug molecules per dendrimer with high solubility (50 mg/mL, vs <0.03 mg/mL for free drug). The conjugate showed extended drug release in human plasma (>72 hours) and inhibited Aspergillus fumigatus growth for >96 hours. These POS-polymer conjugates are novel, highly soluble, and efficient antifungal agents.

Fig. 2 Preparation of POS derivatives A–D. (Tang S, et al., 2021)

References

Tang S, et al. Dendrimer-based posaconazole nanoplatform for antifungal therapy. Drug Deliv. 2021;28(1):2150-2159.

Does Posaconazole require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration. Store in light-resistant containers, preferably original opaque packaging.

What is the recommended storage temperature for Posaconazole?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate oxidative degradation.

Is Posaconazole stable in oral suspension and tablet formulations?

Yes, when formulated with preservatives and protected from light.

How is the impurity posaconazole N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.