NAV

Efinaconazole

Identification

Summary

Efinaconazole is an antifungal agent used to treat onychomycosis, a fungal infection of the nail.

Brand Names
Jublia
Generic Name
Efinaconazole
DrugBank Accession Number
DB09040
Background

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
3D
Similar Structures
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
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Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofOnychomycosis••••••••••••
Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

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 % w/wTopicalBausch Health, Canada Inc.2014-07-21Not applicableCanada flag
JubliaSolution100 mg/1mLTopicalBausch Health US LLC2014-06-06Not applicableUS flag

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)
Affected organisms
  • Candida albicans and other yeasts
  • Yeast and other Trichophyton or Microsporum fungi
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton

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[C@@H](N1CCC(=C)CC1)[C@](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. [Article]
  2. FDA Approved Drug Products: Jublia (efinaconazole) topical solution [Link]
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
FDA label
Download (330 KB)
MSDS
Download (226 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDermatophytosis / Onychomycosis1
4CompletedTreatmentMild to Moderate Onychomycosis Due to Dermatophyte1
4CompletedTreatmentOnychomycosis1
4CompletedTreatmentOnychomycosis of the Toenails1
3CompletedTreatmentOnychomycosis3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionTopical10 % w/w
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
US10828293No2020-11-102034-10-02US flag
US10864274No2020-12-152034-10-02US flag
US10828369No2020-11-102028-01-03US flag
US11213519No2008-01-032028-01-03US flag
US11654139No2014-10-022034-10-02US flag
US11872218No2008-01-032028-01-03US flag

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-MSsplash10-00di-2960000000-1334772d8096be70cc21
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0129000000-5c2c822163a3628871b5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-256202cc7b2acd0b9af1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01wb-6395000000-5ef9aa0794586eff74fe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-3789000000-e5165efa5459f576654d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9010000000-2e7720412f83062150d0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-1922000000-cf78c6b11cba754b3386
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.26985
predicted
DeepCCS 1.0 (2019)
[M+H]+180.62785
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.07826
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lanosterol 14-alpha demethylase
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. [Article]

Drug created at April 21, 2015 16:37 / Updated at April 18, 2024 09:15