AN-2690
AN-2690
CAS: 174671-46-6
Molecular Formula: C7H6BFO2
AN-2690 - Names and Identifiers
AN-2690 - Physico-chemical Properties
| Molecular Formula | C7H6BFO2 |
| Molar Mass | 151.93 |
| Density | 1.28±0.1 g/cm3(Predicted) |
| Melting Point | 120-122℃ |
| Boling Point | 230.8±50.0 °C(Predicted) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | powder |
| Color | white to beige |
| pKa | 6.81±0.20(Predicted) |
| Storage Condition | -20°C |
| Stability | Hygroscopic |
AN-2690 - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 6.582 ml | 32.91 ml | 65.82 ml |
| 5 mM | 1.316 ml | 6.582 ml | 13.164 ml |
| 10 mM | 0.658 ml | 3.291 ml | 6.582 ml |
| 5 mM | 0.132 ml | 0.658 ml | 1.316 ml |
Last Update：2024-01-02 23:10:35
AN-2690 - Reference Information
| Anti-fungal agents | tamoxifen Tavaborole (AN-2690) is AN anti-fungal agent, resistant to Trichophyton, effective treatment of onychomycosis. Tavaborol (Tavaborole, trade name Kerydin)®) is the first boron-based topical antifungal drug from Anacor, Inc., approved by the FDA on 7/7/2014 for the topical treatment of fungal infections of toenails. Anacor focuses on the development and production of boron-based drugs, and according to its latest news, Tavaborole can also be used for fingernail infections in the future. |
| mechanism of action | Tavaborole transfer RNA(tRNA) through the cytoplasm and the synthetase forms an adduct to prevent cellular protein synthesis, thereby exerting its antifungal activity. Simvastatin is a boron-containing antifungal agent with aminoacyl-tRNA synthetase inhibitory effect, which has a unique mechanism of action. tavaborole has been reported to inhibit fungal protein synthesis by inhibiting aminoacyl transfer ribonucleic acid (tRNA) synthetase (AARS), AARS catalyzes the attachment of the correct amino acid to its corresponding tRNA during the translation of the genetic code. Tavaborole was approved by the FDA in 2014 for the treatment of onychomycosis. |
| Drug metabolism | after a single dose, the mean peak concentration (Cmax) of Tavaborole was 3.54±2.26 ng/mL, the mean AUClast was 44.4±25.5 nghr/mL. After 2 weeks of daily dosing, the mean Cmax was 5.17±3.47 ng/mL and the mean AUC τ was 75.8±44.5 ng HR/mL. In addition, Tavaborole showed antifungal effect after 5 days of topical administration with a half-life of 28.5h, and elimination of metabolically produced sulfate conjugates and benzoic acid metabolites mainly by the kidneys. |
| key clinical data | The FDA is based on two multicenter, randomized, A double-blind clinical trial established the efficacy and safety of Tavaborole. The clinical trial compared Tavaborole to topical excipients containing active skin care ingredients. The primary endpoint was "complete cure", defined as complete clean toenails (0% of clinical lesions), while negative KOH tests and cultures determined cure of fungal infection. In both trials, the rates of complete cure were 6.5% and 9.1%, respectively, and the rates of complete cure were 0.5% and 1.5% in the vehicle control group, respectively. The secondary endpoint was a "complete or nearly complete cure", I .e. less than 10% of the concurrent clinical lesions were cured of the fungal infection, or only cured of the fungal infection. Tavaborole showed obvious advantages in both aspects. Tavaborole was generally well tolerated, with most adverse events reported to be mild and unrelated to treatment. Treatment-related adverse events that occurred in more than 1% of participants included application site exfoliation, application site erythema and application site dermatitis, and ingrowth of toenails [5, 6]. |
| editing function of eukaryotic leucyl-tRNA synthetase against broad-spectrum drug AN2690 after transfer | , wang Endo's research group, a researcher in Shanghai Institute of Biochemistry and Cell Biology, Chinese Academy of Sciences, published a research paper in Biochemical Journal: Editing and correction function of eukaryotic leucyl-tRNA synthetase resistant to broad spectrum drug an2690. The group has revealed that leucyl-tRNA synthetases (LeuRS) have multiple redaction pathways, its post-transfer redaction domain is located in the long connecting Peptide 1 (CP1) domain inserted into the active center. Anacor Pharmaceutical Company of the United States has screened a broad-spectrum antifungal drug 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxabol, numbered AN2690, which reduces the aminoacylation activity of yeast LeuRS and loses the post-transfer correction. Biochemical and structural biology studies have confirmed that the compound is covalently bound to the 3 'End of tRNA located in the CP1 domain of the enzyme, and its target is the CP1 domain of fungal LeuRS (Science, 1759, 316, 1761-). Dr. Zhou Xiaolong of Wang Endo's Laboratory studied and compared GlLeuRS and human cytosolic LeuRS(hcLeuRS) based on the study of the structure and function of eukaryotic Giardia LeuRS(GlLeuRS) in CP1, an element called eukaryotic-specific insert 1(Eukarya-Specific Insertion 1, ESI) was found to be involved in amino acid activation, tRNA aminoacylation, and post-transfer editing reactions, but it does not affect the specificity of the editing and correction reaction after the transfer. The study revealed that the post-transfer editing function of GlLeuRS was the result of the synergistic effect of the tRNA binding domain and the CP1 domain at the C- terminal. AN2690 does not affect the tRNA leucine acylation activity of GlLeuRS and the editing and correcting activity after transfer, but affects these two activities of hcLeuRS. This indicates that there is a slight difference in the CP1 domain between GlLeuRS and hbleurs. The introduction of a key mutation point in the CP1 domain of GlLeuRS can restore the effect of AN290 inhibiting both activities. The significance of this work lies in: it is found that the structure of LeuRS changes gradually in the process of evolution, and its function is also fine-tuned accordingly; the differences in the CP1 domains of GlLeuRS and hbleurs will provide a basis for targeting the redacted active domain of GlLeuRS to design a specific drug for the treatment of giardiasis, which should have no effect on human cells. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Product Name: AN-2690 Visit Supplier Webpage Request for quotationCAS: 174671-46-6
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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