| Identification | Back Directory | [Name]
1-[2-methylsulfanyl-1-(2-pentoxyphenyl)ethenyl]imidazole hydrochloride | [CAS]
130773-02-3 | [Synonyms]
SS-717
Atolant
Neticonazole hydrochloride
1-[2-methylsulfanyl-1-(2-pentoxyphenyl)ethenyl]imidazole hydrochloride
1-[(E)-2-methylsulfanyl-1-(2-pentoxyphenyl)ethenyl]imidazole,hydrochloride
(E)-1-(2-(Methylthio)-1-(2-(pentyloxy)phenyl)vinyl)-1H-imidazole hydrochloride
long-acting,colorectal,Neticonazole,antifungal,Neticonazole Hydrochloride,Imidazole,anti-cancer,nSMase2,Fungal,secretion,Inhibitor,p-ERK,anti-infection,inhibit,exosome | [Molecular Formula]
C17H23ClN2OS | [MDL Number]
MFCD00895755 | [MOL File]
130773-02-3.mol | [Molecular Weight]
338.9 |
| Chemical Properties | Back Directory | [Melting point ]
145-147° | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: 250 mg/mL (737.68 mM) | [form ]
Solid | [color ]
White to off-white |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic by ingestion. | [Description]
Neticonazole hydrochloride is a novel imidazole antifungal agent introduced for the
treatment of infections caused by Candida species. One percent neticonazole cream oncedaily
application has been reported to be effective in treating patients with tinea pedis, tinea
corporis, tinea cruris, intertrigo-type candidiasis, erosio interdigitalis and tinea versicolor.
Compared with other agents of the azole class, neticonazole has the most potent activity
against a variety of fungi, including the dermatophytes and pathogenic yeasts. It also has
activity against Gram-positive, but not Gram-negative bacteria. | [Originator]
SS Pharmaceutical (Japan
) | [Definition]
ChEBI: Neticonazole hydrochloride is a hydrochloride resulting from the formal reaction of equimolar amounts of neticonazole and hydrogen chloride. An inhibitor of P450-dependent C-14alpha-demethylation of lanosterol (preventing conversion to ergosterol and inhibiting cell wall synthesis in fungi), it is used in Japan as an antifungal drug for the treatment of superficial skin infections. It has a role as an antifungal drug and an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor. It is a hydrochloride, an imidazole antifungal drug and a conazole antifungal drug. It contains a neticonazole(1+). | [Brand name]
Atolant | [Synthesis]
The general procedure for the synthesis of (E)-1-(2-(methylthio)-1-(2-(pentyloxy)phenyl)ethenyl)-1H-imidazole hydrochloride from 1-iodopentane and (E)-1-[2-methylmercapto-1-[2-hydroxyphenyl]vinyl]-1H-imidazole was carried out as follows: the compound of formula (4) (E)-1-[1-(2-hydroxyphenyl)-2-(methylthio) vinyl]-1H-imidazole (15.1 g, 65 mmol), potassium hydroxide (5.1 g, 91 mmol) and 1-iodopentane (15.55 g, 78 mmol) were dissolved in 75 mL of DMF and the reaction was stirred at room temperature for 3.5 hours. After the reaction was completed, the reaction solution was poured into 375 mL of water and extracted with ethyl acetate, and the organic phase was washed with water and saturated saline in turn. The organic phase was concentrated under reduced pressure to obtain an oil. The oily substance was dissolved in ethyl acetate saturated with hydrogen chloride gas and stirred for 10 hours. A white solid precipitated from the reaction solution, which was filtered, washed with acetonitrile and dried under vacuum to give 16.4 g of white solid product. Yield: 73.2%. HPLC purity (area normalized): 99.61%, single impurity content <0.1%. | [storage]
Store at -20°C | [References]
[1] Patent: CN107556245, 2018, A. Location in patent: Paragraph 0045; 0046 |
|
|