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SML1244

Sigma-Aldrich

Efinaconazole

≥98% (HPLC)

Synonym(s):

(αR,βR)-, α-(2,4-Difluorophenyl)-β-methyl-4-methylene-α-(1H-1,2,4-triazol-1-ylmethyl)-1-piperidineethanol, (2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, KP-103

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About This Item

Empirical Formula (Hill Notation):
C18H22F2N4O
CAS Number:
Molecular Weight:
348.39
UNSPSC Code:
51111800
NACRES:
NA.77

Pricing and availability is not currently available.

Quality Level

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -85 to -95°, c = 1 in chloroform

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

InChI

1S/C18H22F2N4O/c1-13-5-7-23(8-6-13)14(2)18(25,10-24-12-21-11-22-24)16-4-3-15(19)9-17(16)20/h3-4,9,11-12,14,25H,1,5-8,10H2,2H3/t14-,18-/m1/s1

InChI key

NFEZZTICAUWDHU-RDTXWAMCSA-N

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This Item
Z694398Z687820Z694371
suitability

suitable for (multiple organ co-culture)

suitability

suitable for (multiple organ co-culture)

suitability

suitable for (multiple organ co-culture)

suitability

suitable for (multiple organ co-culture)

material

colorless wells, polystyrene

material

clear polystyrene , clear wells

material

colorless wells, polystyrene

material

clear wells, polystyrene

sterility

sterile

sterility

sterile

sterility

sterile

sterility

sterile

packaging

pack of 1 ea

packaging

-

packaging

pack of 5 ea

packaging

-

manufacturer/tradename

Advanced Pharmaceutical Sciences 71011

manufacturer/tradename

Advanced Pharmaceutical Sciences 71044

manufacturer/tradename

Advanced Pharmaceutical Sciences 71010

manufacturer/tradename

Advanced Pharmaceutical Sciences 71043

Application

Efinaconazole has been used as:
  • a topical anti-onychomycosis drug to determine its effects on Trichophyton rubrum and Trichophyton interdigitale[1]
  • as an anti-fungal agent to study its permeability into the nail lysates[2]
  • as an anti-fungal agent to study its effects on Candida africana and Candida dubliniensis[3]

Biochem/physiol Actions

Efinaconazole exhibits its activity against pathogens such as Trichophyton mentagrophytes, Trichophyton rubrum, and Candida albicans. It is active against Candida sp. that cause nail and skin candidiasis. Efinaconazole is also effective against Malassezia sp. that causes tinea versicolor.[4]
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.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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    William J Jo Siu et al.
    Antimicrobial agents and chemotherapy, 57(4), 1610-1616 (2013-01-16)
    Onychomycosis is a common fungal nail infection in adults that is difficult to treat. The in vitro antifungal activity of efinaconazole, a novel triazole antifungal, was evaluated in recent clinical isolates of Trichophyton rubrum, Trichophyton mentagrophytes, and Candida albicans, common
    Gholamreza Shokoohi et al.
    Mycoses, 64(7), 771-779 (2021-04-04)
    Vulvovaginal candidiasis (VVC) is a common and debilitating long-term illness affecting million women worldwide. This disease is caused mainly by Candida albicans and a lesser extent by other species, including the two phylogenetically closely related pathogens Candida africana and Candida
    Keita Sugiura et al.
    Journal of fungi (Basel, Switzerland), 7(3) (2021-04-04)
    To evaluate the combination effects of anti-onychomycosis drugs, the minimum inhibitory concentrations of topical (efinaconazole, luliconazole, and tavaborole) and oral (itraconazole and terbinafine) drugs for Trichophyton rubrum and Trichophyton interdigitale (8 each, with a total of 16 strains) were determined
    Heather Davies-Strickleton et al.
    PloS one, 15(2), e0229414-e0229414 (2020-02-29)
    Onychomycosis, or fungal nail infection, is a common fungal infection largely caused by dermatophyte fungi, such as Trichophyton rubrum or Trichophyton mentagrophytes, which affects a significant number of people. Treatment is either through oral antifungal medicines, which are efficacious but

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