U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16BNO4.C8H8O3
Molecular Weight 389.207
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPETRABOROLE R-MANDELATE

SMILES

O[C@@H](C(O)=O)C1=CC=CC=C1.NC[C@H]2OB(O)C3=C2C=CC=C3OCCCO

InChI

InChIKey=GKQOYBLEEYTDIB-DEZAYANASA-N
InChI=1S/C11H16BNO4.C8H8O3/c13-7-10-8-3-1-4-9(16-6-2-5-14)11(8)12(15)17-10;9-7(8(10)11)6-4-2-1-3-5-6/h1,3-4,10,14-15H,2,5-7,13H2;1-5,7,9H,(H,10,11)/t10-;7-/m11/s1

HIDE SMILES / InChI

Molecular Formula C8H8O3
Molecular Weight 152.1473
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
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
Discovery of a novel class of boron-based antibacterials with activity against gram-negative bacteria.
2013 Mar
Patents

Patents

Sample Use Guides

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 00:26:35 GMT 2023
Edited
by admin
on Sat Dec 16 00:26:35 GMT 2023
Record UNII
VG9GE7GB3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPETRABOROLE R-MANDELATE
WHO-DD  
Common Name English
Epetraborole R-mandelate [WHO-DD]
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, (.ALPHA.R)-, COMPD. WITH 3-(((3S)-3-(AMINOMETHYL)-1,3-DIHYDRO-1-HYDROXY-2,1-BENZOXABOROL-7-YL)OXY)-1-PROPANOL (1:1)
Systematic Name English
Code System Code Type Description
CAS
1234563-15-5
Created by admin on Sat Dec 16 00:26:35 GMT 2023 , Edited by admin on Sat Dec 16 00:26:35 GMT 2023
PRIMARY
FDA UNII
VG9GE7GB3F
Created by admin on Sat Dec 16 00:26:35 GMT 2023 , Edited by admin on Sat Dec 16 00:26:35 GMT 2023
PRIMARY
PUBCHEM
91617525
Created by admin on Sat Dec 16 00:26:35 GMT 2023 , Edited by admin on Sat Dec 16 00:26:35 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY