Tavaborole

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Tavaborole
Tavaborole.svg
Tavaborole ball-and-stick model.png
Names
Trade namesKerydin
Other namesAN2690
  • 5-Fluoro-2,1-benzoxaborol-1(3H)-ol
Clinical data
Drug classAntifungal[1]
Main usesFungal infections of the nail[1]
Side effectsSkin irritation, ingrown toenail[1]
Pregnancy
category
  • US: N (Not classified yet)
Routes of
use
Topical
External links
AHFS/Drugs.comMonograph
US NLMTavaborole
MedlinePlusa614049
Legal
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Chemical and physical data
FormulaC7H6BFO2
Molar mass151.93 g·mol−1
3D model (JSmol)
  • B1(C2=C(CO1)C=C(C=C2)F)O
  • 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, sold under the brand name Kerydin, is an antifungal medication used to treat fungal infections of the nail.[1] It is used by applying it to the nail in question.[1] Evidence supports its use in mild to moderate disease.[2]

Side effects may include skin irritation and an ingrown toenail.[1] It works by inhibits a enzyme, leucyl-tRNA synthetase, that is required for fungus to make protein.[1]

Tavaborole was approved for medical use in the United States in 2014.[3] In the United States 10 ml of solution costs about 1,600 USD as of 2021.[4] It is also available in Canada but not in Europe as of 2018.[5]

Medical uses

Tavaborole is used in the treatment of onychomycosis.[3] 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.[6] It is generally used daily for 48 weeks.[1]

Side effects

Application site skin peeling, skin redness, and irritation are possible side effects, and may occur in less than 5% of individuals.[6]

Pharmacology

Tavaborole acts as an inhibitor of fungal leucyl-tRNA synthetase.[7]

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.[citation needed] 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.[6]

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 an elimination half-life of 28.5 hours, a maximum concentration of 5.17 ng/mL after two weeks of daily use, and takes 8 days to reach the maximum concentration.[6]

History

Tavaborole began phase III clinical trials in December 2010[8] and was approved by the US FDA in July 2014.[9]

Society and culture

Economics

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.[10] A 10 mL bottle of a 5% solution of tavaborole will cost the patient without insurance about $1,356.[11]

See also

Crisaborole – a structurally related topical medication used for the treatment of mild-to-moderate atopic dermatitis (eczema)

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "Tavaborole Monograph for Professionals". Drugs.com. Retrieved 23 September 2021.
  2. Jinna, S; Finch, J (2015). "Spotlight on tavaborole for the treatment of onychomycosis". Drug design, development and therapy. 9: 6185–90. doi:10.2147/DDDT.S81944. PMID 26640371.
  3. 3.0 3.1 Gupta, Aditya K.; Mays, Rachel R.; Folley, Kelly A. (2019). "42. Topical antifungal agents". In Wolverton, Stephen E.; Wu, Jashin J. (eds.). Comprehensive Dermatologic Drug Therapy (4th ed.). Elsevier. p. 488. ISBN 978-0-323-61211-1.
  4. "Kerydin Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 23 September 2021.
  5. Rigopoulos, Dimitris; Elewski, Boni; Richert, Bertrand (6 August 2018). Onychomycosis: Diagnosis and Effective Management. John Wiley & Sons. p. 105. ISBN 978-1-119-22653-6.
  6. 6.0 6.1 6.2 6.3 Elewski BE, Aly R, Baldwin SL, González Soto RF, Rich P, Weisfeld M, et al. (July 2015). "Efficacy and safety of tavaborole topical solution, 5%, a novel boron-based antifungal agent, for the treatment of toenail onychomycosis: Results from 2 randomized phase-III studies". Journal of the American Academy of Dermatology. 73 (1): 62–9. doi:10.1016/j.jaad.2015.04.010. PMID 25956661.
  7. Markinson B, Ghannoum M, Winter T, Rycerz A, Rock F, Gupta AK. Examining the Benefits of the Boron-Based Mechanism of Action and Physicochemical Properties of Tavaborole in the Treatment of Onychomycosis. J Am Podiatr Med Assoc. 2018 Jan;108(1):12-19. doi:10.7547/16-154 PMID 29547036
  8. Clinical trial number NCT01270971 for "Efficacy and Safety Evaluation of AN2690 Topical Solution to Treat Onychomycosis of the Toenail" at ClinicalTrials.gov
  9. "FDA Approves Anacor Pharmaceuticals' KERYDIN™ (Tavaborole) Topical Solution, 5% for the Treatment of Onychomycosis of the Toenails". Market Watch. July 8, 2014.
  10. "Anacor's Kerydin to Be Commercialized by Sandoz in the U.S." Zacks.com. 22 July 2014. Retrieved 7 October 2015.
  11. "Kerydin". Retrieved 12 August 2015.

External links

External sites:
Identifiers: