EPETRABOROLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16BNO4
Molecular Weight	237.06
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC[C@H]1OB(O)C2=C1C=CC=C2OCCCO

InChI

InChIKey=FXQIIDINBDJDKL-SNVBAGLBSA-N

InChI=1S/C11H16BNO4/c13-7-10-8-3-1-4-9(16-6-2-5-14)11(8)12(15)17-10/h1,3-4,10,14-15H,2,5-7,13H2/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H16BNO4
Molecular Weight	237.06
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23295920 | https://newdrugapprovals.org/2015/10/30/gsk-2251052/ | https://adisinsight.springer.com/drugs/800031276

Epetraborole (AN3365 or GSK2251052) is a novel boron-containing antibiotic that inhibits bacterial leucyl tRNA synthetase. It is active against Gram-negative bacteria, including Enterobacteriaceae bearing NDM-1 and KPC carbapenemases, as well as P. aeruginosa. Epetraborole was under development for the treatment of Gram-negative bacterial infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Leucyl-tRNA synthetase (Bacterial) 3 Target ID: Leucyl-tRNA synthetase (Bacterial) Sources: https://adisinsight.springer.com/drugs/800031276 \| https://newdrugapprovals.org/2015/10/30/gsk-2251052/	Inhibitor 8297

PubMed

Title	Date	PubMed
Potency and spectrum of activity of AN3365, a novel boron-containing protein synthesis inhibitor, tested against clinical isolates of Enterobacteriaceae and nonfermentative Gram-negative bacilli.	2013 Jun	23507283
Discovery of a novel class of boron-based antibacterials with activity against gram-negative bacteria.	2013 Mar	23295920

Patents

Sample Use Guides

In Vitro Use Guide

Epetraborole (AN3365 or GSK2251052) (MIC(50/90), 0.5/1 μg/ml) was active against Enterobacteriaceae, including a subset of Klebsiella pneumoniae carbapenemase (KPC)-producing K. pneumoniae strains (MIC(50/90), 1/2 μg/ml). AN3365 inhibited 98.0 and 92.2% of wild-type (MIC(50/90), 2/8 μg/ml) and carbapenem-resistant (MIC(50/90), 4/8 μg/ml) Pseudomonas aeruginosa strains, respectively, at ≤ 8 μg/ml. AN3365 also demonstrated activity against wild-type Acinetobacter baumannii (MIC(50/90), 2/8 μg/ml) and Stenotrophomonas maltophilia (MIC(50/90), 2/4 μg/ml), while it was less active against multidrug-resistant A. baumannii (MIC50/90, 8/16 μg/ml) and Burkholderia cepacia (MIC(50/90), 8/32 μg/ml).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:02:00 GMT 2023` Edited by `admin` on `Sat Dec 16 02:02:00 GMT 2023`
Record UNII	6MC93Z2DF9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPETRABOROLE

Official Name

English

GSK-2251052

Code

English

GSK2251052

Code

English

1-PROPANOL, 3-(((3S)-3-(AMINOMETHYL)-1,3-DIHYDRO-1-HYDROXY-2,1-BENZOXABOROL-7-YL)OXY)-

Systematic Name

English

AN3365

Code

English

epetraborole [INN]

Common Name

English

AN-3365

Code

English

Epetraborole [WHO-DD]

Common Name

English

Code System Code Type Description

DRUG BANK

DB11744