Tavaborole
Identification
- Name
- Tavaborole
- Accession Number
- DB09041
- Description
Tavaborale is a novel, boron-based topical antifungal medication for the treatment of onychomycosis, a fungal infection of the nail and nail bed due to Trichophyton rubrum or Trichophyton mentagrophytes infection. Tavaborole functions by inhibiting Leucyl-tRNA synthetase, or LeuRS, an essential fungal enzyme required for protein synthesis and for the catalysis of ATP-dependent ligation of L-leucine to tRNA(Leu).
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Tavaborole (DB09041)
- Weight
- Average: 151.93
Monoisotopic: 152.044488 - Chemical Formula
- C7H6BFO2
- Synonyms
- 5-Fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
- 5-Fluoro-2,1-benzoxaborol-1(3H)-ol
- Tavaborole
- External IDs
- AN 2690
- AN-2690
- AN2690
Pharmacology
- Indication
Indicated for the treatment of onychomycosis (a fungal infection) of the toenails due to Trichophyton rubrum or Trichophyton mentagrophytes.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
After a single dose, the mean (± standard deviation) peak concentration (Cmax) of tavaborole was 3.54 ± 2.26 ng/mL (n=21 with measurable concentrations, range 0.618-10.2 ng/mL, LLOQ=0.5 ng/mL), and the mean AUClast was 44.4 ± 25.5 nghr/mL (n=21). After 2 weeks of daily dosing, the mean Cmax was 5.17 ± 3.47 ng/mL (n=24, range 1.51-12.8 ng/mL), and the mean AUCτ was 75.8 ± 44.5 nghr/mL.
- Mechanism of action
Tavaborole exerts its antifungal activity by blocking cellular protein synthesis through the formation of an adduct with cytoplasmic leucyl-aminoacyl transfer RNA (tRNA) synthetase.
Target Actions Organism ACytosolic leucyl-tRNA synthetase inhibitorYeast - Absorption
7.5%. Subungual onychomycosis is difficult to treat due to the poorly perfused location of the infection in the nailbed. To be effective, a topical treatment must penetrate the nail plate and reach the site of infection at a concentration sufficient to exert anti-fungal activity. Tavaborole was shown to produce anti-fungal effects after 5 days of topical administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Tavaborole undergoes extensive metabolism. Metabolite profiling revealed trace levels of a sulfated-conjugate and a benzoic acid metabolite, consistent with the known biotransformation of tavaborole.
- Route of elimination
Primarily renal.
- Half-life
28.5 hr
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Tavaborole is generally well tolerated with most adverse events reported as mild and not related to treatment. Treatment related adverse events that occurred in >1 % of participants include application site exfoliation, application site erythema, and application site dermatitis, and ingrown toenail.
- Affected organisms
- 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
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataKerydin Solution 43.5 mg/1mL Topical Anacor Pharmaceuticals, Inc. 2014-07-07 2015-06-04 US 
Kerydin Solution 43.5 mg/1mL Topical Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2014-07-07 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataTavaborole Solution 43.5 mg/1mL Topical Amneal Pharmaceuticals NY LLC 2020-11-28 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Encube Ethicals Private Limited 2020-10-19 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Alembic Pharmaceuticals, Inc. 2020-10-23 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Paddock Laboratories, LLC. 2021-01-10 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Aleor Dermaceuticals Limited 2020-10-23 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- D01AE24 — Tavaborole
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aryl fluorides. These are organic compounds containing the acyl fluoride functional group.
- Kingdom
- Organic compounds
- Super Class
- Organohalogen compounds
- Class
- Aryl halides
- Sub Class
- Aryl fluorides
- Direct Parent
- Aryl fluorides
- Alternative Parents
- Benzenoids / Oxaborole derivatives / Boronic acid esters / Oxacyclic compounds / Organic metalloid salts / Organooxygen compounds / Organofluorides / Organoboron compounds / Hydrocarbon derivatives
- Substituents
- 1,2-oxaborole derivative / Aromatic heteropolycyclic compound / Aryl fluoride / Benzenoid / Boronic acid derivative / Boronic acid ester / Hydrocarbon derivative / Organic metalloid salt / Organic oxygen compound / Organic salt
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, benzoxaborole (CHEBI:77942)
Chemical Identifiers
- UNII
- K124A4EUQ3
- CAS number
- 174671-46-6
- InChI Key
- LFQDNHWZDQTITF-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H6BFO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2
- IUPAC Name
- 5-fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol
- SMILES
- OB1OCC2=CC(F)=CC=C12
References
- General References
- Toledo-Bahena ME, Bucko A, Ocampo-Candiani J, Herz-Ruelas ME, Jones TM, Jarratt MT, Pollak RA, Zane LT: The efficacy and safety of tavaborole, a novel, boron-based pharmaceutical agent: phase 2 studies conducted for the topical treatment of toenail onychomycosis. J Drugs Dermatol. 2014 Sep;13(9):1124-32. [PubMed:25226015]
- Markham A: Tavaborole: first global approval. Drugs. 2014 Sep;74(13):1555-8. doi: 10.1007/s40265-014-0276-7. [PubMed:25118637]
- External Links
- KEGG Drug
- D10169
- PubChem Compound
- 11499245
- PubChem Substance
- 310264989
- ChemSpider
- 9674047
- BindingDB
- 50370987
- 1543173
- ChEBI
- 77942
- ChEMBL
- CHEMBL443052
- ZINC
- ZINC000169990691
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tavaborole
- FDA label
- Download (603 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Onychomycosis / Tinea Unguium 1 3 Completed Treatment Onychomycosis of Toenails 2 2 Completed Treatment Distal, Subungual Onychomycosis 2 2 Completed Treatment Onychomycosis 5 1 Completed Other Onychomycosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Topical 43.5 mg/1mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7582621 Yes 2009-09-01 2027-11-26 US US7767657 No 2010-08-03 2027-05-22 US US9566289 Yes 2017-02-14 2026-08-16 US US9549938 Yes 2017-01-24 2026-08-16 US US9566290 Yes 2017-02-14 2026-08-16 US US9572823 Yes 2017-02-21 2026-08-16 US Additional Data Available- Filed OnFiled OnAvailable 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
Property Value Source Water Solubility 11.3 mg/mL ALOGPS logP 1.51 ALOGPS logP 2.24 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 8.91 ChemAxon pKa (Strongest Basic) -4.8 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 29.46 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 33.86 m3·mol-1 ChemAxon Polarizability 14.21 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes 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
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Leucine-trna ligase activity
- Specific Function
- Not Available
- Gene Name
- CDC60
- Uniprot ID
- Q9HGT2
- Uniprot Name
- Cytosolic leucyl-tRNA synthetase
- Molecular Weight
- 125454.54 Da
References
- Toledo-Bahena ME, Bucko A, Ocampo-Candiani J, Herz-Ruelas ME, Jones TM, Jarratt MT, Pollak RA, Zane LT: The efficacy and safety of tavaborole, a novel, boron-based pharmaceutical agent: phase 2 studies conducted for the topical treatment of toenail onychomycosis. J Drugs Dermatol. 2014 Sep;13(9):1124-32. [PubMed:25226015]
Drug created on April 23, 2015 11:24 / Updated on June 12, 2020 11:42