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Key Documents

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:
164650-44-6
Molecular Weight:
348.39
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

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

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

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.
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
GHS08

Signal Word

Warning

Hazard Statements

H361

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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