Identification
- Summary
Tavaborole is an antifungal agent used to treat onychomycosis, a fungal infection of the nail.
- Brand Names
- Kerydin
- Generic Name
- Tavaborole
- DrugBank Accession Number
- DB09041
- Background
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.3
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Onychomycosis of the toenails caused by trichophyton mentagrophytes •••••••••••• •••••••• Treatment of Onychomycosis of the toenails caused by trichophyton rubrum •••••••••••• •••••••• - Contraindications & Blackbox Warnings
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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 Aleucine--tRNA ligase inhibitorTrichophyton rubrum - 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
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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.
- 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 Kerydin Solution 43.5 mg/1mL Topical Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2014-07-07 Not applicable US 
Kerydin Solution 43.5 mg/1mL Topical Anacor Pharmaceuticals, Inc. 2014-07-07 2015-06-04 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tavaborole Solution 43.5 mg/1mL Topical Chartwell Rx, Llc 2021-02-03 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical bryant ranch prepack 2021-01-10 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Padagis US LLC 2021-01-10 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Cipla USA Inc. 2021-02-18 Not applicable US Tavaborole Solution 43.5 mg/1mL Topical Aleor Dermaceuticals Limited 2020-10-23 Not applicable US
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)
- Affected organisms
- Yeast and other Trichophyton or Microsporum fungi
- Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
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. [Article]
- Markham A: Tavaborole: first global approval. Drugs. 2014 Sep;74(13):1555-8. doi: 10.1007/s40265-014-0276-7. [Article]
- FDA Approved Drug Products: KERYDIN (tavaborole) topical [Link]
- 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 the 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 Liquid Topical 43.5 mg/1mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7582621 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
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Trichophyton rubrum
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Aminoacyl-trna editing activity
- Gene Name
- Not Available
- Uniprot ID
- A0A178ESV1
- Uniprot Name
- leucine--tRNA ligase
- Molecular Weight
- 127117.965 Da
References
- Mazzantini D, Celandroni F, Calvigioni M, Lupetti A, Ghelardi E: In Vitro Resistance and Evolution of Resistance to Tavaborole in Trichophyton rubrum. Antimicrob Agents Chemother. 2021 Mar 18;65(4):e02324-20. doi: 10.1128/AAC.02324-20. Print 2021 Mar 18. [Article]
- Zane LT, Plattner J, Chanda S, Coronado D, Merchant T, Alley MR, Gupta AK: Tavaborole topical solution, 5% for the treatment of toenail onychomycosis. Drugs Today (Barc). 2015 Oct;51(10):599-607. doi: 10.1358/dot.2015.51.10.2401004. [Article]
Drug created at April 23, 2015 17:24 / Updated at February 27, 2023 22:24