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164650-44-6

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164650-44-6 Usage

Description

Different sources of media describe the Description of 164650-44-6 differently. You can refer to the following data:
1. In October 2013, efinaconazole (also known as KP-103) was approved in Canada as a 10% topical solution for the treatment of onychomycosis. Like other azole antifungal agents, efinaconazole acts by disrupting fungal cell membranes through inhibition of sterol 14α-demethylase, an enzyme involved in the biosynthesis of ergosterol, which is a key component of the fungal cell membrane. Efinaconazole has potent antifungal activity against clinical isolates of dermatophytes, including Trichophyton mentagrophyes (MIC80 =0.125 μg/mL) and Trichophyton rubrum (MIC80 =0.25 μg/mL), as well as against Candida and Malassezia species. Unlike other antifungal agents, efinaconazole retains activity in the presence of keratin, indicating that more unbound drug is available at the site of action. Efinaconazole is efficacious in guinea-pig models of fungal infection. Efinaconazole is prepared by reaction of an epoxide intermediate with 4-methylenepiperidine.
2. Efinaconazole is a broad-spectrum triazole antifungal agent with activity against Acremonium, Aspergillus, Candida, Cryptococcus, Epidermophyton, Fusarium, Microsporum, Paecilomyces, Pseudallescheria, Scopulariopsis, Trichophyton, and Trichosporon. It inhibits the growth of T. rubrum and T. mentagrophytes clinical isolates with MIC values ranging from ≤2.0 to 60 ng/ml and of C. albicans isolates with MIC values ranging from ≤0.5 to >250 ng/ml. Efinaconazole inhibits sterol 14α-demethylase, which arrests ergosterol biosynthesis at the fungal membrane. It inhibits ergosterol biosynthesis in T. mentagrophytes and C. albicans with IC50 values of 7.0 and 0.40 ng/ml, respectfully. Topical formulations containing efinaconazole have been used for the treatment of onychomycosis.

Originator

Kaken Pharmaceuticals (Japan)

Uses

Efinaconazole has been used as:a topical anti-onychomycosis drug to determine its effects on Trichophyton rubrum and Trichophyton interdigitaleas an anti-fungal agent to study its permeability into the nail lysatesas an anti-fungal agent to study its effects on Candida africana and Candida dubliniensis

Definition

ChEBI: A member of the class of triazoles that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,4-difluorophenyl, and 4-methylenepiperidin-1-yl groups, respectively (the 2R,3R stereoisomer). It is an antifungal drug used for the topical treatment of onychomycosis (a nail infection caused mainly by dermatophytes).

Brand name

Jublia

Biochem/physiol Actions

Efinaconazole is a triazole antifungal drug approved clinically for the treatment of nail fungus (Onychomycosis). It inhibits sterol biosynthesis by inhibition of cytochrome P450 14α-demethylase, an enzyme in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. Efinaconazole has better nail penetration, so is more effective than other topical agents and as effective as oral medication for nail fungus.

Synthesis

Commercially available (R)-methyl lactate (55) was first converted to THP protected alcohol 57 in 4 steps and 78% yield via morpholino amide 56. Grignard displacement of the morpholine afforded ketone 58 in 81% yield. Next, ketone 58 was epoxidized by means of the Corey ylide followed by ring-opening of the epoxide by triazole which had been activated by exposure to sodium tbutoxide. Finally, subjection to methanesulfonic acid furnished diol 59 in 51% yield as the corresponding mesylate salt. Diol 59 was then converted to epoxide 60 through the use of mesyl chloride and triethylamine in 78% yield and >99% ee. Finally, treatment of epoxide 60 with 4-methylene piperidine–HBr in the presence of lithium hydroxide afforded efinaconazole (VIII) in 87% yield.

Check Digit Verification of cas no

The CAS Registry Mumber 164650-44-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,4,6,5 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 164650-44:
(8*1)+(7*6)+(6*4)+(5*6)+(4*5)+(3*0)+(2*4)+(1*4)=136
136 % 10 = 6
So 164650-44-6 is a valid CAS Registry Number.

164650-44-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name efinaconazole

1.2 Other means of identification

Product number -
Other names Efinaconazole [USAN:INN]

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:164650-44-6 SDS

164650-44-6Downstream Products

164650-44-6Relevant articles and documents

Identification, synthesis, and control of efinaconazole impurities

Zhu, Fuqiang,Zhang, Jian,Xiamuxi, Hainimu,Chen, Weiming,Hu, Tianwen,Yang, Xiaojun,Tian, Guanghui,Ni, Runyan,Li, Jian,Suo, Jin,Xie, Yuanchao,Shen, Jingshan,Aisa, Haji A.,He, Yang

, p. 438 - 441 (2018)

Impurities A-F were observed, identified, and confirmed during the efinaconazole production process. The possible formation pathways of the mentioned impurities were understood, and thereafter, a controlling strategy was established by locating the proper process parameters with the consideration of efficient cost and less waste as well. This impurity investigation is also essential for quality control of consistently delivering of qualified efinaconazole API.

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai

supporting information, p. 6961 - 6966 (2021/09/11)

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

PREPARATION METHOD FOR EFINACONAZOLE

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Paragraph 0031-0048, (2021/11/26)

The present invention provides a preparation method for Efinaconazole, comprising the following steps: in the presence of a bromide and a base, subjecting (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazole-1-yl)methyl]oxirane and an inorganic a

METHOD OF PRODUCING 1-TRIAZOLE-2-BUTANOL DERIVATIVES

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Paragraph 0039-0066, (2018/05/15)

PROBLEM TO BE SOLVED: To provide a novel method of producing 1-triazole-2-butanol derivatives useful as pharmaceuticals. SOLUTION: A method of producing a 1-triazole 2-butanol derivative represented by formula (1) comprises reacting a compound represented by formula (2) with 4-methylenepiperidine (3) in the presence of a metal salt (excluding lithium salts). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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