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Key Documents

SML1244

Sigma-Aldrich

Efinaconazole

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C18H22F2N4O
Numéro CAS:
164650-44-6
Poids moléculaire :
348.39
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

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

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

−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

Clé InChI

NFEZZTICAUWDHU-RDTXWAMCSA-N

Application

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

Actions biochimiques/physiologiques

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.
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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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