Itraconazole

Itraconazole (R51211) is a triazole antifungal agent and a potent and orally active Hedgehog (Hh) signaling pathway antagonist with an IC50 of ~800 nM. Itraconazole potently inhibits lanosterol 14α-demethylase (cytochrome P450 enzyme), thereby inhibits the oxidative conversion of lanosterol to ergosterol. Itraconazole has anticancer and antiangiogenic effects. Itraconazole is a oxysterol-binding protein (OSBP) inhibitor[1][2][3][4].

Product Specifications

CAS Number

[84625-61-6]

Product Name Alternative

R51211

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Antibiotic; Autophagy; Bacterial; Cytochrome P450; Fungal; Hedgehog

Type

Reference compound

Related Pathways

Anti-infection; Autophagy; Metabolic Enzyme/Protease; Stem Cell/Wnt

Applications

COVID-19-immunoregulation

Field of Research

Infection; Cancer

Assay Protocol

https://www.medchemexpress.com/Itraconazole.html

Purity

99.59

Solubility

DMSO : 6.25 mg/mL (ultrasonic)

Smiles

ClC1=C(C=CC(Cl)=C1)[C@@]2(O[C@@H](COC3=CC=C(N4CCN(C5=CC=C(N(C=NN6C(C)CC)C6=O)C=C5)CC4)C=C3)CO2)CN7C=NC=N7

Molecular Formula

C35H38Cl2N8O4

Molecular Weight

705.63

Precautions

H302, H315, H319, H335

References & Citations

[1]Kim, J., et al., Itraconazole, a commonly used antifungal that inhibits Hedgehog pathway activity and cancer growth. Cancer Cell, 2010. 17 (4) : p. 388-99.|[2]Chong, C.R., et al., Inhibition of angiogenesis by the antifungal drug itraconazole. ACS Chem Biol, 2007. 2 (4) : p. 263-70.|[3]Pace JR, et al. Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic. J Med Chem. 2016 Apr 28;59 (8) :3635-49.|[4]Albulescu L, et al. Uncovering oxysterol-binding protein (OSBP) as a target of the anti-enteroviral compound TTP-8307. Antiviral Res. 2017;140:37-44.