Efinaconazole

Synonyms :
(2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylene-1-piperidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Status : approved

Description

Efinaconazole is a 14 alpha-demethylase inhibitor indicated in the treatment of fungal infection of the nail, known as onychomycosis. It was approved for use in Canada and the USA in 2014 and is marketed by Valeant Pharmaceuticals North America LLC under the name Jublia.

Used

Indicated in the treatment of fungal infection of the nail, known as onychomycosis.

Mechanism Of Action

Efinaconazole is an azole antifungal. Efinaconazole inhibits fungal lanosterol 14α-demethylase involved in the biosynthesis of ergosterol, a constituent of fungal cell membranes.

Dosage

Form Route Strength
Solution topical 10 %
Solution topical 100 mg/mL

Pharmacodynamics

mean ± SD plasma Cmax on Day 28 of treatment: 0.67 ± 0.37 ng/mL.
mean ± SD AUC was 12.15 ± 6.91 ng*h/mL.

Half Life

29.9 hours in healthy patients.

Chemical Classification

This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Amphetamines and derivatives

Organic compounds

Benzenoids

Benzene and substituted derivatives

Phenethylamines

Chemical Name

(2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylene-1-piperidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Brands

name Dosage form Country
Jublia solution Canada
Jublia solution US

Calculated Property

kind Value Source
logP 1.49 ALOGPS
logS -2.8 ALOGPS
Water Solubility 6.10e-01 g/l ALOGPS
logP 2.24 ChemAxon
IUPAC Name (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylidenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol ChemAxon
Traditional IUPAC Name (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylidenepiperidin-1-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol ChemAxon
Molecular Weight 348.398 ChemAxon
Monoisotopic Weight 348.17616767 ChemAxon
SMILES C[C@@H](N1CCC(=C)CC1)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1 ChemAxon
Molecular Formula C18H22F2N4O ChemAxon
InChI 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 ChemAxon
InChIKey NFEZZTICAUWDHU-RDTXWAMCSA-N ChemAxon
Polar Surface Area (PSA) 54.18 ChemAxon
Refractivity 103.94 ChemAxon
Polarizability 34.48 ChemAxon
Rotatable Bond Count 5 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest acidic) 12.7 ChemAxon
pKa (strongest basic) 7.45 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Candida albicans and other yeasts

Target within organism

  • Lanosterol 14-alpha demethylase : in Yeast