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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O6S
Molecular Weight 277.254
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DURLOBACTAM

SMILES

CC1=C[C@@H]2C[N@]([C@@H]1C(N)=O)C(=O)N2OS(O)(=O)=O

InChI

InChIKey=BISPBXFUKNXOQY-RITPCOANSA-N
InChI=1S/C8H11N3O6S/c1-4-2-5-3-10(6(4)7(9)12)8(13)11(5)17-18(14,15)16/h2,5-6H,3H2,1H3,(H2,9,12)(H,14,15,16)/t5-,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula C8H11N3O6S
Molecular Weight 277.254
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Durlobactam is a new member of the diazabicyclooctane class of beta-lactamase inhibitors with broad-spectrum activity against Ambler class A, C, and D serine beta-lactamases. Sulbactam is a first-generation beta-lactamase inhibitor with activity limited to a subset of class A enzymes that also has direct-acting antibacterial activity against Acinetobacter spp. The latter feature is due to sulbactam's ability to inhibit certain penicillin-binding proteins, essential enzymes involved in bacterial cell wall synthesis in this pathogen. Because sulbactam is also susceptible to cleavage by numerous beta-lactamases, its clinical utility for the treatment of contemporary Acinetobacter infections is quite limited. However, when combined with durlobactam, the activity of sulbactam is effectively restored against these notoriously multidrug-resistant strains. In May 2023, the FDA approved Innoviva’s antibiotic, sulbactam-durlobactam (Xacduro), for treatment in patients 18 years of age and older for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP) caused by susceptible isolates of ABC.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
XACDURO

Approved Use

XACDURO is a co-packaged product containing sulbactam, a beta-lactam antibacterial and beta lactamase inhibitor, and durlobactam, a beta lactamase inhibitor, indicated in patients 18 years of age and older for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of Acinetobacter baumannii-calcoaceticus complex.

Launch Date

2023
Curative
XACDURO

Approved Use

XACDURO is a co-packaged product containing sulbactam, a beta-lactam antibacterial and beta lactamase inhibitor, and durlobactam, a beta lactamase inhibitor, indicated in patients 18 years of age and older for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of Acinetobacter baumannii-calcoaceticus complex.

Launch Date

2023
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
29.2 μg/mL
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
25.5 μg/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
38.7 μg/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
33.3 μg/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
27 μg/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
28.6 μg/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.9 μg/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
39.9 μg/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
471 μg × h/mL
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
659 μg × h/mL
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
895 μg × h/mL
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1743 μg × h/mL
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
202 μg × h/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
209 μg × h/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
151 μg × h/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
110 μg × h/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
280 μg × h/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
123 μg × h/mL
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
123.8 μg × h/mL
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.51 h
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.4 h
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.8 h
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3 h
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.29 h
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.1 h
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.1 h
500 mg 4 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.2 h
1000 mg 4 times / day steady-state, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
1 g 4 times / day steady-state, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered: SULBACTAM
DURLOBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >1000 uM]
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Sulbactam-durlobactam for infections caused by Acinetobacter baumannii-calcoaceticus complex.
2023-08
Durlobactam, a Broad-Spectrum Serine β-lactamase Inhibitor, Restores Sulbactam Activity Against Acinetobacter Species.
2023-05-01
Acinetobacter baumannii Resistance to Sulbactam/Durlobactam: A Systematic Review.
2022-12-10
Durlobactam in the Treatment of Multidrug-Resistant Acinetobacter baumannii Infections: A Systematic Review.
2022-06-07
Durlobactam, a New Diazabicyclooctane β-Lactamase Inhibitor for the Treatment of Acinetobacter Infections in Combination With Sulbactam.
2021
Patents

Sample Use Guides

Administer XACDURO (1 g of sulbactam, 1 g of durlobactam) every 6 hours by intravenous (IV) infusion over 3 hours in patients with creatinine clearance (CLcr) of 45 to 129 mL/min. (2.1) • Dosing regimen adjustments are recommended for CLcr less than 45 mL/min and CLcr greater than or equal to 130 mL/min. (2.2) • Administer all doses of XACDURO by IV infusion over 3 hours. (2.3)
Route of Administration: Intravenous
In Vitro Use Guide
Durlobactam sodium salt is an inhibitor of beta-lactamase with IC50 values of 4 nM, 14 nM, and 190 nM for Class A KPC-2, Class C AmpC, and Class D OXA-24, respectively.
Substance Class Chemical
Created
by admin
on Tue Apr 01 21:23:18 GMT 2025
Edited
by admin
on Tue Apr 01 21:23:18 GMT 2025
Record UNII
PSA33KO9WA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DURLOBACTAM
INN   USAN  
Official Name English
ETX-2514
Preferred Name English
(2S,5R)-2-CARBAMOYL-3-METHYL-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-3-EN-6-YL SULFATE
Common Name English
SULFURIC ACID, MONO((2S,5R)-2-(AMINOCARBONYL)-3-METHYL-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-3-EN-6-YL) ESTER
Systematic Name English
durlobactam [INN]
Common Name English
ETX2514
Code English
DURLOBACTAM [USAN]
Common Name English
Durlobactam [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
89851852
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
NCI_THESAURUS
C174851
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
DAILYMED
PSA33KO9WA
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
USAN
GH-68
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
SMS_ID
100000183570
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
FDA UNII
PSA33KO9WA
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
CAS
1467829-71-5
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
INN
10824
Created by admin on Tue Apr 01 21:23:18 GMT 2025 , Edited by admin on Tue Apr 01 21:23:18 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY