Itraconazole

SKU: orb1310057

Description

Itraconazole (R51211) is an orally active triazole antifungal agent that also acts as a Hedgehog pathway antagonist, an OSBP inhibitor, and a cytochrome P450 enzyme inhibitor. It is widely used in research for studying antifungal mechanisms, cancer signaling pathways, and lipid transport in both in vitro and in vivo models.

Research Area

Cell Biology, Infectious Disease & Virology, Metabolism Research, Pharmacology & Drug Discovery, Stem Cell & Developmental Biology

Key Properties

• CAS Number: 84625-61-6
• MW: 705.63
• Purity: 99.90%
• Formula: C₃₅H₃₈Cl₂N₈O₄
• SMILES: C([C@]1(O[C@@H](COC2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)N5C(=O)N(C(CC)C)N=C5)CO1)C6=C(Cl)C=C(Cl)C=C6)N7C=NC=N7
• Target: Cytochromes P450,Autophagy,Hedgehog/Smoothened,Antibacterial,Antibiotic,Antifungal
• Solubility: 10% DMSO+40% PEG300+5% Tween 80+45% Saline:0.71 mg/mL (1.01 mM);DMSO:8 mg/mL (11.34 mM)

Bioactivity

• Target IC50:
  CYP3A4:6.1 nM
• In Vivo:
  Itraconazole exhibits affinity for mammalian cytochrome P-450 enzymes and fungal P-450-dependent enzymes, thereby possessing potential for clinically significant interactions with azoles (e.g., simvastatin, terfenadine, rifampin, oral contraceptives, H2 receptor antagonists, warfarin, cyclosporine). Metabolized into hydroxy-itraconazole (OH-ITZ) and two novel metabolites, keto-itraconazole (keto-ITZ) and N-desalkyl itraconazole (ND-ITZ), its metabolites are inhibitors of CYP3A4 as potent, or more so, than itraconazole itself. Itraconazole acts on the hedgehog (Hh) signaling pathway component Smoothened with a mechanism distinct from cyclopamine and other known SMO antagonists, preventing SMO accumulation stimulated by Hh activation. It inhibits 60 clinical isolates of Aspergillus with MICs at 0.25 mg/mL, primarily by damaging ergosterol synthesis, leading to defective fungal cell membranes with altered permeability and function.
• In Vitro:
  Like other Hedgehog (Hh) pathway antagonists, Itraconazole can inhibit the activity of the Hh pathway and the growth of medulloblastoma in a murine syngeneic transplant model.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Triazole, Smoothened, R 51211, R-51211, R51211, Inhibitor, Itraconazole, inhibit, lanosterol, Hedgehog, Fungal, ergosterol, Cytochrome P450, CYP-450, CYP3A4, CYPs, 14α-demethylase, anticancer, Antibiotic, antifungal, antiangiogenic, Autophagy

Compound Identifiers

PubChem CID

55283