Tavaborole

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
ACytosolic leucyl-tRNA synthetase
inhibitor
Yeast
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
Adverseeffects
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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.

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

Products2
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KerydinSolution43.5 mg/1mLTopicalAnacor Pharmaceuticals, Inc.2014-07-072015-06-04US flag
KerydinSolution43.5 mg/1mLTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2014-07-07Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TavaboroleSolution43.5 mg/1mLTopicalLupin Pharmaceuticals, Inc.2021-07-09Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalMayne Pharma Inc.2021-02-01Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalEncube Ethicals Private Limited2020-10-19Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalCipla USA Inc.2021-02-18Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalAlembic Pharmaceuticals, Inc.2020-10-23Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalTaro Pharmaceuticals U.S.A., Inc.2021-05-07Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalPaddock Laboratories, LLC.2021-01-10Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalbryant ranch prepack2021-01-10Not applicableUS flag
TavaboroleLiquid43.5 mg/1mLTopicalEstreno Pharma, LLC2021-02-04Not applicableUS flag
TavaboroleSolution43.5 mg/1mLTopicalAleor Dermaceuticals Limited2020-10-23Not applicableUS flag

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
  1. 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]
  2. Markham A: Tavaborole: first global approval. Drugs. 2014 Sep;74(13):1555-8. doi: 10.1007/s40265-014-0276-7. [Article]
  3. FDA Approved Drug Products: KERYDIN (tavaborole) topical [Link]
KEGG Drug
D10169
PubChem Compound
11499245
PubChem Substance
310264989
ChemSpider
9674047
BindingDB
50370987
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentOnychomycosis / Tinea Unguium1
3CompletedTreatmentOnychomycosis of Toenails2
2CompletedTreatmentDistal, Subungual Onychomycosis2
2CompletedTreatmentOnychomycosis5
1CompletedOtherOnychomycosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionTopical43.5 mg/1mL
LiquidTopical43.5 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7582621Yes2009-09-012027-11-26US flag
US7767657No2010-08-032027-05-22US flag
US9566289Yes2017-02-142026-08-16US flag
US9549938Yes2017-01-242026-08-16US flag
US9566290Yes2017-02-142026-08-16US flag
US9572823Yes2017-02-212026-08-16US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.3 mg/mLALOGPS
logP1.51ALOGPS
logP2.24ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.86 m3·mol-1ChemAxon
Polarizability14.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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

Drugtargets2
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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
  1. 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]

Drug created on April 23, 2015 17:24 / Updated on August 07, 2021 00:11