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
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
| 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.
Originator
Approval Year
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. | 2013-06 |
|
| Discovery of a novel class of boron-based antibacterials with activity against gram-negative bacteria. | 2013-03 |
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
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VG9GE7GB3F
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