84604-65-9

Basic information

• Product Name: ()-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one
• Synonyms: cis-Itraconazole; (1)-cis-4-(4-(4-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one
• CAS NO: 84604-65-9
• Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
• Molecular Weight: 705.643
• EINECS: 283-347-2
• Mol File: 84604-65-9.mol

Chemical Properties

• CAS DataBase Reference: ()-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: ()-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one(84604-65-9)
• EPA Substance Registry System: ()-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one(84604-65-9)

Safety Data

• Hazardous Substances Data: 84604-65-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
()-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one is used as an antifungal agent for its ability to inhibit the synthesis of ergosterol, which is a critical component of fungal cell membranes. This makes it effective against a broad spectrum of fungal pathogens and useful in treating various fungal infections.
Additionally, it has demonstrated antiparasitic properties and is under investigation for potential applications in treating parasitic infections, further expanding its utility in the pharmaceutical domain.

Upstream product

• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 252964-68-4 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 106461-41-0 (-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-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 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 

Downstream Products

• 154003-17-5 (2R,4S,2'S)-Itraconazole 
• 154003-18-6 (2R,4S,2'R)-Itraconazole 
• 154003-19-7 (2S,4R,2'S)-Itraconazole 
• 154003-20-0 (2S,4R,2'R)-Itraconazole 

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.

Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction

The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).