AN-2718

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6BClO2
Molecular Weight	168.385
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OB1OCC2=C1C=CC(Cl)=C2

InChI

InChIKey=HMAFTPZYFJFEHK-UHFFFAOYSA-N

InChI=1S/C7H6BClO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2

HIDE SMILES / InChI

Molecular Formula	C7H6BClO2
Molecular Weight	168.385
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800019312 | https://idsa.confex.com/idsa/2008/webprogram/Paper27819.html

AN-2718 is a member of a new class of antifungals, benzoxaboroles, which inhibit fungal growth by blocking protein synthesis. AN-2718 is being developed for the topical treatment of tinea pedis including the hard to treat mocassin-type, which at present is only treatable with oral antifungals. AN-2718 inhibits an essential protein synthesis enzyme, leucyl-transfer RNA synthetase, or LeuRS. AN-2718 Inhibits LeuRS by the OBORT mechanism of trapping tRNALEU in the editing site of LeuRS. AN-2718 has good MIC90 activity against the dermatophytes, T. rubrum and T. mentagrophytes, which supports its use as a topical agent to treat tinea pedis. AN-2718 has been used in trials studying Tinea Pedis, but its development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UNIPROT: Q9HGT2 (Cytosolic leucyl-tRNA synthetase) 1 Target ID: UNIPROT: Q9HGT2 (Cytosolic leucyl-tRNA synthetase) Sources: https://idsa.confex.com/idsa/2008/webprogram/Paper27819.html	Inhibitor 8297		4.2 µM [IC50]

PubMed

Title	Date	PubMed
Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (AN2690), for the potential treatment of onychomycosis.	2006 Jul 27	16854048

Patents

Sample Use Guides

In Vitro Use Guide

AN-2718 has a broad-spectrum of antifungal activity with MIC90 of 1 ug/mL, 0.25 ug/mL, 1 ug/mL, 0.5 ug/mL for C. albicans (n=100), C. glabrata (n=100), Trichophyton mentagrophytes (n=100) and T. rubrum respectively (n=100). AN-2718 inhibits cytoplasmic LeuRS from molds, A. fumigatus, and from yeasts, C. albicans, with an IC50 of 2 uM and 4.2 uM, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:50:19 GMT 2023` Edited by `admin` on `Sat Dec 16 06:50:19 GMT 2023`
Record UNII	810U6C2DGG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AN-2718

Common Name

English

2,1-BENZOXABOROLE, 5-CHLORO-1,3-DIHYDRO-1-HYDROXY-

Systematic Name

English

AN2718

Common Name

English

Code System Code Type Description

FDA UNII

810U6C2DGG