Tavaborole

Systematic (IUPAC) name
5-Fluoro-2,1-benzoxaborol-1(3H)-ol
Clinical data
Trade names	Kerydin
Legal status	℞ (Prescription only)
Routes of administration	Topical
Identifiers
CAS Number	174671-46-6
ATC code	None
PubChem	CID: 11499245
ChemSpider	9674047
UNII	K124A4EUQ3 Y
KEGG	D10169
Synonyms	AN2690
Chemical data
Formula	C7H6BFO2
Molecular mass	151.93 g/mol
SMILES B1(C2=C(CO1)C=C(C=C2)F)O
InChI InChI=1S/C7H6BFO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2 Key:LFQDNHWZDQTITF-UHFFFAOYSA-N

Tavaborole (AN2690, trade name Kerydin) is a topical antifungal medication for the treatment of onychomycosis, a fungal infection of the nail and nail bed. Tavaborole began its Phase 3 trials in December 2010 and was approved in July 2014. Tavaborole inhibits an essential fungal enzyme, leucyl-tRNA synthetase, that is required for protein synthesis. The inhibition of protein synthesis leads to termination of cell growth and then cell death, eliminating the fungal infection.

Pharmacokinetics

Tavaborole, when prepared with a 1:1 mixture of ethyl acetate and propylene glycol, has the ability to fully penetrate through the human nail. In studies with cadaver fingernails, a 5% solution of tavaborole penetrated the nail an average of 524.7 mcg/cm² after two weeks of daily use.

Clinical

Tavaborole is detectable in the blood at a level of 3.54 ng/mL after a single use of 0.2 mL of the 5% solution. Tavaborole has a half-life in the blood of 28.5 hrs, a maximum concentration of 5.17 ng/mL after two weeks of daily use, and takes 8.03 days to reach the maximum concentration.

Therapeutic trials

In clinical trials, tavaborole was more effective than the vehicle (ethyl acetate and propylene glycol) alone in curing onychomycosis. In two studies, fungal infection was eliminated using tavaborole in 6.5% of the cases vs. 0.5% using the vehicle alone, and 27.5% vs. 14.6% using the vehicle alone.

Adverse effects

Application site exfoliation, erythema (rash), and irritation are all possible side effects, though they occur in less than 5% of the patents tested.

Commercial

Originally developed by Anacor, it is now marketed in the United States by Novartis subsidiary Sandoz. Anacor was paid US$65 million and also entered into a profit sharing scheme for future sales. A 10mL bottle of a 5% solution of Tavaborole will cost the patient about $1,356.