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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16BNO4.ClH
Molecular Weight 273.521
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPETRABOROLE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=DADYQGIQOBJGIW-HNCPQSOCSA-N
InChI=1S/C11H16BNO4.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 01:19:41 GMT 2023
Edited
by admin
on Sat Dec 16 01:19:41 GMT 2023
Record UNII
MM0NZY12FA
Record Status Validated (UNII)
Record Version
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Name Type Language
EPETRABOROLE HYDROCHLORIDE
WHO-DD  
Common Name English
1-PROPANOL, 3-(((3S)-3-(AMINOMETHYL)-1,3-DIHYDRO-1-HYDROXY-2,1-BENZOXABOROL-7-YL)OXY)-, HYDROCHLORIDE (1:1)
Systematic Name English
Epetraborole hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 860621
Created by admin on Sat Dec 16 01:19:42 GMT 2023 , Edited by admin on Sat Dec 16 01:19:42 GMT 2023
Code System Code Type Description
CAS
1234563-16-6
Created by admin on Sat Dec 16 01:19:41 GMT 2023 , Edited by admin on Sat Dec 16 01:19:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT002062
Created by admin on Sat Dec 16 01:19:42 GMT 2023 , Edited by admin on Sat Dec 16 01:19:42 GMT 2023
PRIMARY
PUBCHEM
52918389
Created by admin on Sat Dec 16 01:19:42 GMT 2023 , Edited by admin on Sat Dec 16 01:19:42 GMT 2023
PRIMARY
FDA UNII
MM0NZY12FA
Created by admin on Sat Dec 16 01:19:42 GMT 2023 , Edited by admin on Sat Dec 16 01:19:42 GMT 2023
PRIMARY
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