Efinaconazole

Identification

Name
Efinaconazole
Accession Number
DB09040
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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 348.398
Monoisotopic: 348.17616767
Chemical Formula
C18H22F2N4O
Synonyms
  • (2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylene-1-piperidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol
  • efinaconazol
  • Efinaconazole
External IDs
  • IDP 108
  • IDP-108
  • IDP108
  • KP 103
  • KP-103

Pharmacology

Indication

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

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

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.

TargetActionsOrganism
ALanosterol 14-alpha demethylase
inhibitor
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life

29.9 hours in healthy patients.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Candida albicans and other yeasts
  • Yeast and other Trichophyton or Microsporum fungi
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
JubliaSolution10 %TopicalBausch Health, Canada Inc.2014-07-21Not applicableCanada flag
JubliaSolution100 mg/1mLTopicalBausch Health US LLC2014-06-06Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
D01AC19 — Efinaconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Fluorobenzenes / Aralkylamines / Piperidines / Aryl fluorides / Triazoles / Tertiary alcohols / Heteroaromatic compounds / Trialkylamines / 1,2-aminoalcohols
show 5 more
Substituents
1,2,4-triazole / 1,2-aminoalcohol / Alcohol / Amine / Amphetamine or derivatives / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, organofluorine compound, tertiary alcohol, tertiary amino compound, triazole antifungal drug, conazole antifungal drug, olefinic compound (CHEBI:82718)

Chemical Identifiers

UNII
J82SB7FXWB
CAS number
164650-44-6
InChI Key
NFEZZTICAUWDHU-RDTXWAMCSA-N
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
IUPAC Name
(2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylidenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
SMILES
C[[email protected]@H](N1CCC(=C)CC1)[[email protected]](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

References

General References
  1. Patel T, Dhillon S: Efinaconazole: first global approval. Drugs. 2013 Nov;73(17):1977-83. doi: 10.1007/s40265-013-0152-x. [PubMed:24249649]
KEGG Drug
D10021
PubChem Compound
489181
PubChem Substance
310264988
ChemSpider
428538
RxNav
1539753
ChEBI
82718
ChEMBL
CHEMBL2103877
ZINC
ZINC000000006251
Drugs.com
Drugs.com Drug Page
Wikipedia
Efinaconazole
AHFS Codes
  • 84:04.08.08 — Azoles
FDA label
Download (330 KB)
MSDS
Download (226 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentMild to Moderate Onychomycosis Due to Dermatophyte1
4CompletedTreatmentDermatophytosis / Onychomycosis1
4CompletedTreatmentOnychomycosis1
4CompletedTreatmentOnychomycosis of Toenail1
3CompletedTreatmentOnychomycosis3
2CompletedTreatmentOnychomycosis1
Not AvailableCompletedOtherEvaluation of Jublia on Nail Polish With Healthy Toenails1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionTopical10 %
SolutionTopical100 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7214506No2007-05-082021-10-05US flag
US8039494No2011-10-182030-07-08US flag
US8486978No2013-07-162030-10-24US flag
US9302009No2016-04-052030-10-24US flag
US9662394No2017-05-302034-10-02US flag
US9566272No2017-02-142028-01-03US flag
US9861698No2018-01-092030-07-08US flag
US9877955No2018-01-302028-01-03US flag
US10105444No2018-10-232030-07-08US flag
US10512640No2019-12-242028-01-03US flag
US10478601No2019-11-192035-04-25US flag
US10342875No2019-07-092034-10-02US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.61 mg/mLALOGPS
logP1.49ALOGPS
logP2.24ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.94 m3·mol-1ChemAxon
Polarizability34.48 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol (By similarity).
Gene Name
ERG11
Uniprot ID
P50859
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
61304.95 Da
References
  1. Patel T, Dhillon S: Efinaconazole: first global approval. Drugs. 2013 Nov;73(17):1977-83. doi: 10.1007/s40265-013-0152-x. [PubMed:24249649]

Drug created on April 21, 2015 10:37 / Updated on November 25, 2020 08:53

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