Itraconazole

SKU: orb1310057

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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

Cardiovascular Research, Cell Biology

Images & Validation

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Key Properties

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CAS Number	84625-61-6
MW	705.6
Purity	>98%
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	GPCR
Solubility	Soluble in DMSO (up to 1.5 mg/ml with warming)

Bioactivity

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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. Read more...
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. Read more...

Storage & Handling

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Storage	-20°C
Expiration Date	12 months from date of receipt.
Disclaimer	For research use only

Alternative Names

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Oriconazole; R51211

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Compound Identifiers

PubChem CID

55283 ↗

Key Properties

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No computed properties available.

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Itraconazole (orb1310057)

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CAS Number:	112560-33-5
MW:	719.62
Formula:	C₃₅H₃₆Cl₂N₈O₅

Purity:	99.59% (May vary between batches)
CAS Number:	112559-91-8
MW:	721.63
Formula:	C₃₅H₃₈Cl₂N₈O₅

Purity:	98.01% (May vary between batches)
CAS Number:	106461-41-0
MW:	393.48
Formula:	C₂₂H₂₇N₅O₂

Purity:	>98% (HPLC)
CAS Number:	182760-06-1
MW:	437.47
Formula:	C₂₂H₁₇F₂N₅OS

Purity:	>98% (HPLC)
CAS Number:	1776-30-3
MW:	240.25
Formula:	C₁₅H₁₂O₃?

Itraconazole

Description

Research Area

Images & Validation

Key Properties

Bioactivity

Storage & Handling

Alternative Names

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Itraconazole (orb1310057)

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