1309272-50-1
Chemical Structure
Itraconazole-d9
Synonym(s): R51211-d9
- CAS No.: 1309272-50-1
- Formula:C35H29D9Cl2N8O4
- Molecular Weight:714.69
IUPAC Name: 4-(4-(4-(4-(((2R,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(butan-2-yl-d9)-2,4-dihydro-3H-1,2,4-triazol-3-one
InChIKey: VHVPQPYKVGDNFY-FALIESLJSA-N
SMILES: O=C(N(N=C1)C(C([2H])([2H])[2H])([2H])C([2H])([2H])C([2H])([2H])[2H])N1C(C=C2)=CC=C2N(CC3)CCN3C(C=C4)=CC=C4OC[C@@H](CO5)O[C@]5(C6=C(C=C(C=C6)Cl)Cl)CN7C=NC=N7
Biological Activity: Itraconazole-d9 is the deuterium labeled Itraconazole[1]. 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[2][3][4][5].
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Itraconazole-d9 | 97.86% | Itraconazole-d9 is the deuterium labeled 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. | ||||||||||||||||||||
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Itraconazole (Standard) | ≥98% | Itraconazole (Standard) is the analytical standard of Itraconazole. This product is intended for research and analytical applications. 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. | ||||||||||||||||||||
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Itraconazole-d5 | 99.55% | Itraconazole-d5 is the deuterium labeled 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. | ||||||||||||||||||||
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Itraconazole-d3 | 99.62% | Itraconazole-d3 (R51211-d3) is the deuterium labeled Itraconazole (HY-17514). 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. | ||||||||||||||||||||
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Itraconazole | 99.59% | 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. | ||||||||||||||||||||
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- [1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216. [Content Brief]
- [2]. 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. [Content Brief]
- [3]. Chong, C.R., et al., Inhibition of angiogenesis by the antifungal drug itraconazole. ACS Chem Biol, 2007. 2(4): p. 263-70. [Content Brief]
- [4]. 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. [Content Brief]
- [5]. 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.
