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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H16N4O7S
Molecular Weight 324.311
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NACUBACTAM

SMILES

NCCONC(=O)[C@@H]1CC[C@@H]2C[N@]1C(=O)N2OS(O)(=O)=O

InChI

InChIKey=RSBPYSTVZQAADE-RQJHMYQMSA-N
InChI=1S/C9H16N4O7S/c10-3-4-19-11-8(14)7-2-1-6-5-12(7)9(15)13(6)20-21(16,17)18/h6-7H,1-5,10H2,(H,11,14)(H,16,17,18)/t6-,7+/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H16N4O7S
Molecular Weight 324.311
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Nacubactam (FPI-1459) was developed as an antibacterial drug. Nacubactam successfully has completed phase I clinical trials for the treatment of serious gram-negative bacterial infections. The drug is currently being developed for the treatment of complicated urinary tract infection, hospital-acquired bacterial pneumonia, ventilator-associated bacterial pneumonia, and complicated intra-abdominal infections. FPI-1459 works through several mechanisms of action, inhibiting a number of beta-lactamase enzymes as well as certain bacterial cell wall enzymes. In January 2019, FPI-1459 received Fast Track and Qualified Infectious Disease Product designations from the U.S. Food and Drug Administration (FDA).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.0 nM [IC50]

Sample Use Guides

Participants will receive a single 2000 milligram (mg) intravenous (IV) infusion of nacubactam over 1.5 hours.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:38:16 GMT 2023
Edited
by admin
on Sat Dec 16 11:38:16 GMT 2023
Record UNII
832O37V7MZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NACUBACTAM
INN   WHO-DD  
INN  
Official Name English
SULFURIC ACID, MONO((1R,2S,5R)-2-(((2-AMINOETHOXY)AMINO)CARBONYL)-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-6-YL) ESTER, (-)-
Common Name English
RO-7079901
Code English
(1R,2S,5R)-2-((2-AMINOETHOXY)CARBAMOYL)-7-OXO- 1,6-DIAZABICYCLO(3.2.1)OCTAN-6-YL HYDROGEN SULFATE
Systematic Name English
RG-6080
Code English
FPI-1459
Code English
NACUBACTAM [USAN]
Common Name English
SULFURIC ACID, MONO((1R,2S,5R)-2-(((2-AMINOETHOXY)AMINO)CARBONYL)-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-6-YL) ESTER
Systematic Name English
RO7079901
Code English
Nacubactam [WHO-DD]
Common Name English
nacubactam [INN]
Common Name English
Code System Code Type Description
CAS
1452458-86-4
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
PUBCHEM
73386748
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
FDA UNII
832O37V7MZ
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
USAN
EF-79
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
DRUG BANK
DB15353
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
SMS_ID
100000174644
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
INN
10300
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
NCI_THESAURUS
C175153
Created by admin on Sat Dec 16 11:38:16 GMT 2023 , Edited by admin on Sat Dec 16 11:38:16 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
A diazabicyclooctane beta-lactamase inhibitor, for treating bacterial infection. In July 2016, nacubactam was reported to be in phase 1 clinical development. Sulfuric acid, mono((1R,2S,5R)-2-(((2-aminoethoxy)amino)carbonyl)-7-oxo-1,6-diazabicyclo(3.2.1)oct-6-yl) ester A .BETA.-lactamase inhibitor potentially for the treatment of bacterial infections.