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
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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.
Target Actions Organism 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jublia Solution 100 mg/1mL Topical Bausch Health US LLC 2014-06-06 Not applicable US Jublia Solution 10 % w/w Topical Bausch Health, Canada Inc. 2014-07-21 Not applicable Canada
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
- External Links
- KEGG Drug
- D10021
- PubChem Compound
- 489181
- PubChem Substance
- 310264988
- ChemSpider
- 428538
- 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
Phase Status Purpose Conditions Count 4 Completed Treatment Dermatophytosis / Onychomycosis 1 4 Completed Treatment Mild to Moderate Onychomycosis Due to Dermatophyte 1 4 Completed Treatment Onychomycosis 1 4 Completed Treatment Onychomycosis of the Toenails 1 3 Completed Treatment Onychomycosis 3 2 Completed Treatment Onychomycosis 1 Not Available Completed Other Evaluation of Jublia on Nail Polish With Healthy Toenails 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Topical 10 % w/w Solution Topical 100 mg/1mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7214506 No 2007-05-08 2021-10-05 US US8039494 No 2011-10-18 2030-07-08 US US8486978 No 2013-07-16 2030-10-24 US US9302009 No 2016-04-05 2030-10-24 US US9662394 No 2017-05-30 2034-10-02 US US9566272 No 2017-02-14 2028-01-03 US US9861698 No 2018-01-09 2030-07-08 US US9877955 No 2018-01-30 2028-01-03 US US10105444 No 2018-10-23 2030-07-08 US US10512640 No 2019-12-24 2028-01-03 US US10478601 No 2019-11-19 2035-04-25 US US10342875 No 2019-07-09 2034-10-02 US US10828293 No 2020-11-10 2034-10-02 US US10864274 No 2020-12-15 2034-10-02 US US10828369 No 2020-11-10 2028-01-03 US US11213519 No 2008-01-03 2028-01-03 US US11654139 No 2014-10-02 2034-10-02 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.61 mg/mL ALOGPS logP 1.49 ALOGPS logP 2.24 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 12.7 Chemaxon pKa (Strongest Basic) 7.45 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.18 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 103.94 m3·mol-1 Chemaxon Polarizability 34.48 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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
- 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 December 06, 2023 02:33