Cas no 67914-61-8 (Deacetyl Ketoconazole)

Deacetyl Ketoconazole is a derivative of the antifungal agent Ketoconazole, characterized by the removal of the acetyl group from its molecular structure. This modification enhances its metabolic stability and bioavailability compared to its parent compound. It exhibits potent antifungal activity by inhibiting ergosterol synthesis, disrupting fungal cell membrane integrity. Deacetyl Ketoconazole is particularly effective against dermatophytes, yeasts, and other pathogenic fungi. Its improved pharmacokinetic profile allows for lower dosing frequencies while maintaining therapeutic efficacy. The compound is commonly utilized in topical formulations for treating cutaneous fungal infections due to its targeted action and reduced systemic absorption. Its stability and solubility properties make it suitable for various pharmaceutical applications.
Deacetyl Ketoconazole structure
Deacetyl Ketoconazole structure
Product Name:Deacetyl Ketoconazole
CAS No:67914-61-8
MF:C24H26Cl2N4O3
MW:489.394243717194
MDL:MFCD00872139
CID:967761
PubChem ID:12854716
Update Time:2025-05-22

Deacetyl Ketoconazole Chemical and Physical Properties

Names and Identifiers

    • cis-1-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
    • Deacetyl Ketoconazole
    • (+/-)-DAK
    • KETOCONAZOLE IMPURITY D
    • R 39519
    • DEACETYLKETOCONAZOLE
    • P7P4A1FD7Z
    • KETOCONAZOLE IMPURITY D [EP IMPURITY]
    • PIPERAZINE, 1-(4-(((2R,4S)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-, REL-
    • Piperazine, 1-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, cis-
    • 1-[4-[[(2RS,4SR)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
    • 1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
    • N-Desacetyl Ketonazole
    • cis-1-(4-((2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
    • A1-01723
    • 1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl) piperazine
    • MFCD00872139
    • EINECS 267-745-3
    • N-DEACETYLKETOCONAZOLE-(+/-)-
    • Q27286330
    • Ketoconazole Imp. D (EP); 1-[4-[[(2RS,4SR)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; Ketoconazole Impurity D
    • N-Deacetylketoconazole
    • CHEMBL372799
    • 67914-61-8
    • UNII-P7P4A1FD7Z
    • 1-(4-(((2RS,4SR)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE
    • SCHEMBL15940936
    • AS-6141
    • R-39519
    • rel-1-(4-(((2R,4S)-2-((1H-Imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
    • AKOS027250804
    • Deacylketoconazole
    • DB-243276
    • 1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
    • MDL： MFCD00872139
    • Inchi： 1S/C24H26Cl2N4O3/c25-18-1-6-22(23(26)13-18)24(16-29-10-7-28-17-29)32-15-21(33-24)14-31-20-4-2-19(3-5-20)30-11-8-27-9-12-30/h1-7,10,13,17,21,27H,8-9,11-12,14-16H2/t21-,24-/m0/s1
    • InChI Key： LOUXSEJZCPKWAX-URXFXBBRSA-N
    • SMILES： ClC1C=C(C=CC=1[C@@]1(CN2C=NC=C2)OC[C@H](COC2C=CC(=CC=2)N2CCNCC2)O1)Cl

Computed Properties

  • Exact Mass: 488.1381961g/mol
  • Monoisotopic Mass: 488.1381961g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 7
  • Complexity: 621
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.4
  • Topological Polar Surface Area: 60.8?2

Experimental Properties

  • Density: 1.39±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 173 oC
  • Boiling Point: 699.7±55.0 °C at 760 mmHg
  • Flash Point: 376.9±31.5 °C
  • Solubility: Very slightly soluble (0.11 g/l) (25 o C),
  • Vapor Pressure: 0.0±2.2 mmHg at 25°C

Deacetyl Ketoconazole Security Information

Deacetyl Ketoconazole Pricemore >>

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Chemenu
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 67914-61-8 95%
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Chemenu
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1-(4-(((2R,4S)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
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TRC
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(CAS:67914-61-8)Deacetyl Ketoconazole
Order Number:A1030361
Stock Status:in Stock
Quantity:100mg/250mg/1g
Purity:99%
Pricing Information Last Updated:Thursday, 29 August 2024 15:39
Price ($):174.0/349.0/878.0

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Additional information on Deacetyl Ketoconazole

Research Brief on Deacetyl Ketoconazole (CAS: 67914-61-8): Recent Advances and Applications

Deacetyl Ketoconazole (CAS: 67914-61-8), a metabolite of the antifungal agent Ketoconazole, has garnered significant attention in recent years due to its unique pharmacological properties and potential therapeutic applications. This research brief aims to synthesize the latest findings on Deacetyl Ketoconazole, focusing on its chemical characteristics, biological activities, and emerging roles in drug development.

Recent studies have highlighted the compound's distinct mechanism of action compared to its parent molecule, Ketoconazole. While Ketoconazole primarily functions as a cytochrome P450 (CYP) inhibitor, Deacetyl Ketoconazole exhibits a more selective inhibition profile, particularly targeting CYP3A4 with reduced off-target effects. This selectivity has sparked interest in its potential as a safer alternative for certain clinical applications, especially in scenarios where drug-drug interactions are a concern.

In the realm of antifungal research, novel formulations incorporating Deacetyl Ketoconazole have demonstrated improved pharmacokinetic properties. A 2023 study published in the Journal of Medicinal Chemistry reported that nanoparticle-encapsulated Deacetyl Ketoconazole showed enhanced bioavailability and tissue penetration compared to conventional formulations. This advancement could address longstanding challenges in treating systemic fungal infections, particularly in immunocompromised patients.

Beyond its antifungal applications, recent investigations have explored Deacetyl Ketoconazole's potential in oncology. Preliminary in vitro studies suggest that the compound may modulate androgen receptor signaling pathways, making it a candidate for prostate cancer research. However, these findings require further validation through comprehensive preclinical and clinical studies to establish efficacy and safety profiles.

The metabolic pathways of Deacetyl Ketoconazole have also been a focus of recent research. Advanced analytical techniques, including LC-MS/MS and NMR spectroscopy, have provided new insights into its biotransformation processes. These studies are crucial for understanding potential drug interactions and optimizing dosing regimens in clinical settings.

From a chemical synthesis perspective, recent advancements have improved the yield and purity of Deacetyl Ketoconazole production. Green chemistry approaches have been successfully applied to reduce environmental impact while maintaining high product quality. These developments are particularly relevant for pharmaceutical manufacturers scaling up production for clinical trials.

Regulatory considerations surrounding Deacetyl Ketoconazole continue to evolve as new data emerges. Current discussions focus on establishing appropriate guidelines for its use as both a therapeutic agent and a reference standard in analytical applications. The compound's unique properties present both opportunities and challenges in regulatory classification.

Looking forward, the research landscape for Deacetyl Ketoconazole appears promising. Ongoing clinical trials are expected to provide critical data on its therapeutic potential, while continued mechanistic studies may uncover novel applications. The compound's versatility positions it as a valuable asset in both pharmaceutical development and basic research within the chemical biology domain.

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Amadis Chemical Company Limited
(CAS:67914-61-8)Deacetyl Ketoconazole
A1030361
Purity:99%/99%/99%
Quantity:100mg/250mg/1g
Price ($):174.0/349.0/878.0
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