Itraconazole

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Cat.No. 5981 - Itraconazole | C35H38Cl2N8O4 | CAS No. 84625-61-6
Description: SMO antagonist; acts at different binding site to cyclopamine (Cat No. 1623)
Chemical Name: 4-[4-[4-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one
Purity: ≥99% (HPLC)
Datasheet
Citations
Reviews
Literature

Biological Activity

SMO antagonist (IC50 = 690 nM); acts at different binding site to cyclopamine (Cat. No. 1623). Also cytochrome p450 inhibitor (IC50 = 16-26 nM). Inhibits cell cycle at G1 phase in vitro and blocks angiogenesis in vivo (IC50 = 160 nM). Antifungal.

Technical Data

M. Wt 705.63
Formula C35H38Cl2N8O4
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 84625-61-6
PubChem ID 3793
InChI Key VHVPQPYKVGDNFY-UHFFFAOYSA-N
Smiles CCC(N1N=CN(C2=CC=C(N3CCN(C4=CC=C(C=C4)OC[C@H]5CO[C@@](O5)(C6=C(C=C(C=C6)Cl)Cl)CN7C=NC=N7)CC3)C=C2)C1=O)C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 14.11 20mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 705.63. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.42 mL 7.09 mL 14.17 mL
5 mM 0.28 mL 1.42 mL 2.83 mL
10 mM 0.14 mL 0.71 mL 1.42 mL
50 mM 0.03 mL 0.14 mL 0.28 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Chong et al (2007) Inhibition of angiogenesis by the antifungal drug itraconazole. ACS Chem.Biol. 2 263 PMID: 17432820

Kim et al (2013) Itraconazole and arsenic trioxide inhibit Hedgehog pathway activation and tumor growth associated with acquired resistance to smoothened antagonists. Cancer Cell 23 23 PMID: 23291299

Kim et al (2010) Itraconazole, a commonly used antifungal that inhibits Hedgehog pathway activity and cancer growth. Cancer Cell 17 388 PMID: 20385363

Pace et al (2016) Repurposing the clinically efficacious antifungal agent itraconazole as an anticancer chemotherapeutic. J.Med.Chem. 59 3635 PMID: 27014922


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Keywords: Itraconazole, supplier, SMO, antagonists, smoothened, receptors, cytochrome, p450, inhiibitors, inhibits, cell, cycle, angiogenesis, antifungals, hedgehog, Smoothened, Receptors, Antiangiogenics, Cell, Cycle, Inhibitors, Antibiotics, Smoothened, Receptors, Tocris Bioscience

Citations for Itraconazole

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Literature in this Area

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