74855-91-7

Basic information

• Product Name: Propyl Itraconazole
• Synonyms: Propyl Itraconazole;Itraconazole EP IMpurity C;Itraconazole iMpurity C;)-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-propyl-3H-1,2,4-triazol-3-one;cis-(±cis-(±)-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-propyl-3H-1,2,4-triazol-3-one;4-[4-[4-[4-[[cis-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxyphenyl]piperazin-1-yl]phenyl]-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one;Itraconazole Propyl Analog
• CAS NO: 74855-91-7
• Molecular Formula: C34H36Cl2N8O4
• Molecular Weight: 691.60684
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74855-91-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Propyl Itraconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Propyl Itraconazole(74855-91-7)
• EPA Substance Registry System: Propyl Itraconazole(74855-91-7)

Safety Data

• Hazardous Substances Data: 74855-91-7(Hazardous Substances Data)

Usage

Description

Propyl Itraconazole, also known as Itraconazole EP Impurity C, is a novel derivative of Itraconazole (I937500), which is an antimycotic azole. It is characterized by its potent antifungal properties and is currently being explored for its potential applications in various fields, including COVID-19 research.

Uses

Used in Pharmaceutical Industry:
Propyl Itraconazole is used as an antimycotic agent for treating various fungal infections. Its potent antifungal activity makes it a valuable asset in the pharmaceutical industry for developing new treatments and therapies.
Used in COVID-19 Research:
Propyl Itraconazole is also used as a research product in the context of COVID-19. Its potential applications in this area are currently being investigated, with the aim of understanding its effectiveness against the virus and its possible role in the development of new treatments for COVID-19.

Upstream product

• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 79538-91-3 4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 113770-65-3 2RS,4RS-toluene-4-sulfonic acid (2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl ester 
• 74852-92-9 4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 100-00-5 4-chlorobenzonitrile 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 67914-86-7 cis-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate 
• 154003-21-1 ((2S,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methyl 4-methyl-benzenesulfonate 
• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 
• 74852-62-3 4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine 
• 74853-06-8 phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate 
• 74852-89-4 N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarboxamide 

Relevant articles and documents

Repurposing the Clinically Efficacious Antifungal Agent Itraconazole as an Anticancer Chemotherapeutic

Itraconazole (ITZ) is an FDA-approved member of the triazole class of antifungal agents. Two recent drug repurposing screens identified ITZ as a promising anticancer chemotherapeutic that inhibits both the angiogenesis and hedgehog (Hh) signaling pathways. We have synthesized and evaluated first- and second-generation ITZ analogues for their anti-Hh and antiangiogenic activities to probe more fully the structural requirements for these anticancer properties. Our overall results suggest that the triazole functionality is required for ITZ-mediated inhibition of angiogenesis but that it is not essential for inhibition of Hh signaling. The synthesis and evaluation of stereochemically defined des-triazole ITZ analogues also provides key information as to the optimal configuration around the dioxolane ring of the ITZ scaffold. Finally, the results from our studies suggest that two distinct cellular mechanisms of action govern the anticancer properties of the ITZ scaffold.

Itraconazole Side Chain Analogues: Structure-Activity Relationship Studies for Inhibition of Endothelial Cell Proliferation, Vascular Endothelial Growth Factor Receptor 2 (VEGFR2) Glycosylation, and Hedgehog Signaling

Itraconazole is an antifungal drug that was recently found to possess potent antiangiogenic activity and anti-hedgehog (Hh) pathway activity. To search for analogues of itraconazole with greater potency and to understand the structure-activity relationship in both antiangiogenic and Hh targeting activity, 25 itraconazole side chain analogues were synthesized and assayed for inhibition of endothelial cell proliferation and Gli1 transcription in a medulloblastoma (MB) culture. Through this analysis, we have identified analogues with increased potency for inhibiting endothelial cell proliferation and the Hh pathway, as well as VEGFR2 glycosylation that was recently found to be inhibited by itraconazole. An SAR analysis of these activities revealed that potent activity of the analogues against VEGFR2 glycosylation was generally driven by side chains of at least four carbons in composition with branching at the α or β position. SAR trends for targeting the Hh pathway were divergent from those related to HUVEC proliferation or VEGFR2 glycosylation. These results also suggest that modification of the sec-butyl side chain can lead to enhancement of the biological activity of itraconazole.