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

Download

MOLSDFPDBSMILESInChI

Similar Structures

Structure for Tavaborole (DB09041)

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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.

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Associated Conditions

• Onychomycosis

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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

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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

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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
Kerydin	Solution	43.5 mg/1mL	Topical	Anacor Pharmaceuticals, Inc.	2014-07-07	2015-06-04

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Tavaborole	Solution	43.5 mg/1mL	Topical	Lupin Pharmaceuticals, Inc.	2021-07-09	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Aleor Dermaceuticals Limited	2020-10-23	Not applicable
Tavaborole	Liquid	43.5 mg/1mL	Topical	Estreno Pharma, LLC	2021-02-04	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Amneal Pharmaceuticals NY LLC	2020-11-28	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Taro Pharmaceuticals U.S.A., Inc.	2021-05-07	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Encube Ethicals Private Limited	2020-10-19	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Mayne Pharma Inc.	2021-02-01	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	bryant ranch prepack	2021-01-10	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Alembic Pharmaceuticals, Inc.	2020-10-23	Not applicable
Tavaborole	Solution	43.5 mg/1mL	Topical	Cipla USA Inc.	2021-02-18	Not applicable

Categories

ATC Codes

D01AE24 — Tavaborole

• D01AE — Other antifungals for topical use
• D01A — ANTIFUNGALS FOR TOPICAL USE
• D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

Drug Categories

• Anti-Infective Agents
• Antifungal Agents
• Antifungals for Dermatological Use
• Antifungals for Topical Use
• Dermatologicals
• Oxaborole Antifungal
• Protein Synthesis Inhibitors

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]

External Links

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

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
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
US7767657	No	2010-08-03	2027-05-22
US9566289	Yes	2017-02-14	2026-08-16
US9549938	Yes	2017-01-24	2026-08-16
US9566290	Yes	2017-02-14	2026-08-16
US9572823	Yes	2017-02-21	2026-08-16

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

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Details1. Cytosolic leucyl-tRNA synthetase

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]

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