AN-2690 - CAS 174671-46-6
Catalog number: 174671-46-6
Category: Inhibitor
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Molecular Formula:
C7H6BFO2
Molecular Weight:
151.93
COA:
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Targets:
Antifungal
Description:
Tavaborole (AN2690) is a potent antifungal that targets the post-transfer editing site of leucyl-tRNA synthetase (LeuRS). Tavaborole forms a covalent adduct with the 3' adenosine of tRNA(leu) at the editing site of fungal, but not bacterial LeuRS, locking the enzyme in an inactive conformation. Tavaborole was recently approved for the treatment of onychomycosis of the toenail in adults.
Purity:
>98%
Synonyms:
Tavaborole; AN2690; AN 2690
MSDS:
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InChIKey:
LFQDNHWZDQTITF-UHFFFAOYSA-N
InChI:
InChI=1S/C7H6BFO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2
Canonical SMILES:
B1(C2=C(CO1)C=C(C=C2)F)O
1.Spotlight on tavaborole for the treatment of onychomycosis.
Jinna S1, Finch J1. Drug Des Devel Ther. 2015 Nov 20;9:6185-90. doi: 10.2147/DDDT.S81944. eCollection 2015.
Onychomycosis is a fungal nail plate infection that has been increasing in prevalence. A variety of oral and topical anti-fungal agents are currently available but their use is limited by their adverse effect profile, drug-drug interactions, and limited efficacy. Therefore, there is a great need for newer anti-fungal agents. Tavaborole is one of these newer agents and was approved by the US Food and Drug Administration in July 2014 for the topical treatment of mild to moderate toenail onychomycosis. Tavaborole is a novel, boron-based anti-fungal agent with greater nail plate penetration than its predecessors, due to its smaller molecular weight. It has proven through several Phase II and III trials that it can be a safe and effective topical agent for the treatment of mild to moderate toenail onychomycosis without the need for debridement. In this paper, we review the landscape of topical and systemic treatment of onychomycosis, with particular attention to the pharmacokinetics, safety, and efficacy of topical tavaborole.
2.Efinaconazole and Tavaborole: Emerging Antifungal Alternatives for the Topical Treatment of Onychomycosis.
Poulakos M1, Grace Y2, Machin JD1, Dorval E1. J Pharm Pract. 2016 Feb 11. pii: 0897190016630904. [Epub ahead of print]
PURPOSE: The purpose of this article is to review the safety, efficacy, and role of efinaconazole and tavaborole in the treatment of onychomycosis.
3.Tavaborole, a Novel Boron-Containing Small Molecule Pharmaceutical Agent for Topical Treatment of Onychomycosis: I. Reproductive and Developmental Toxicity Studies.
Ciaravino V1, Coronado D2, Lanphear C3, Hoberman A4, Chanda S2. Int J Toxicol. 2016 Apr 4. pii: 1091581816639113. [Epub ahead of print]
Tavaborole is a topical antifungal agent approved by the US Food and Drug Administration for the treatment of toenail onychomycosis. As part of the nonclinical development program, reproductive and developmental toxicity studies were conducted (rat oral fertility and early embryonic development, rat (oral) and rabbit (dermal) embryo-fetal development). There were no effects on fertility or reproductive performance at doses up to 300 mg/kg/d (107 times the maximum recommended human dose [MRHD] based on mean area under the plasma concentration-time curve comparisons). In the rat embryo-fetal development toxicity studies, teratogenicity was not observed at doses up to 100 mg/kg/d (29 times the MRHD). However, several treatment-related skeletal malformations and variations were observed at 300 mg/kg/d (570 times the MRHD). In rabbit embryo-fetal development toxicity studies dosed via oral or dermal administration, the no observable adverse effect level for maternal toxicity and embryo-fetal toxicity was 50 mg/kg/d (16 times the MRHD) and 5% (26 times the MRHD), respectively.
4.Evaluation of the Appearance of Nail Polish Following Daily Treatment of Ex Vivo Human Fingernails With Topical Solutions of Tavaborole or Efinaconazole.
Coronado D, Vlahovic TC, Chanda S, Merchant T, Zane LT. J Drugs Dermatol. 2016 Jan 1;15(1):89-94.
INTRODUCTION: Patients with onychomycosis may mask infected nails with polish. Tavaborole topical solution, 5% is a boron-based, small-molecule pharmaceutical approved for the treatment of toenail onychomycosis caused by <em>Trichophyton rubrum</em> and <em>Trichophyton mentagrophytes</em>; efinaconazole topical solution, 10% is approved for the same indication. Nail polish appearance after application of tavaborole (dropper) or efinaconazole (brush); respective applicator appearance; presence of color transfer from respective applicators; and color transfer to remaining solutions after dosing of polished nails were evaluated.<br/>
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CAS 174671-46-6 AN-2690

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