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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H10N3O6S.Na
Molecular Weight 299.236
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DURLOBACTAM SODIUM

SMILES

[Na+].CC1=C[C@@H]2C[N@]([C@@H]1C(N)=O)C(=O)N2OS([O-])(=O)=O

InChI

InChIKey=WHHNOICWPZIYKI-IBTYICNHSA-M
InChI=1S/C8H11N3O6S.Na/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);/q;+1/p-1/t5-,6+;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H10N3O6S
Molecular Weight 276.247
Charge -1
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
Durlobactam, a New Diazabicyclooctane β-Lactamase Inhibitor for the Treatment of Acinetobacter Infections in Combination With Sulbactam.
2021
Acinetobacter baumannii Resistance to Sulbactam/Durlobactam: A Systematic Review.
2022 Dec 10
Durlobactam in the Treatment of Multidrug-Resistant Acinetobacter baumannii Infections: A Systematic Review.
2022 Jun 7
Sulbactam-durlobactam for infections caused by Acinetobacter baumannii-calcoaceticus complex.
2023 Aug
Durlobactam, a Broad-Spectrum Serine β-lactamase Inhibitor, Restores Sulbactam Activity Against Acinetobacter Species.
2023 May 1
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
F78MDZ9CW9
Record Status Validated (UNII)
Record Version
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Name Type Language
DURLOBACTAM SODIUM
USAN  
Official Name English
XACDURO COMPONENT DURLOBACTAM SODIUM
Preferred Name English
Durlobactam sodium [WHO-DD]
Common Name English
DURLOBACTAM SODIUM [USAN]
Common Name English
ETX-2514 SODIUM
Code English
SODIUM (2S,5R)-2-CARBAMOYL-3-METHYL-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-3-EN-6-YL SULFATE
Common Name English
ETX2514 SODIUM
Code English
(1R,2S,5R)-2-Carbamoyl-3-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl sodium sulfate
Systematic Name English
Code System Code Type Description
DAILYMED
F78MDZ9CW9
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
100000183473
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
F78MDZ9CW9
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
C171695
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
PUBCHEM
89851851
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
1467157-21-6
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-69
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
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY