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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
190.0 nM [IC50] | |||
4.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | XACDURO Approved UseXACDURO 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 Date2023 |
|||
Curative | XACDURO Approved UseXACDURO 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 Date2023 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.01506-19 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.01506-19 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.00794-19 |
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 CLINICAL TRIAL https://journals.asm.org/doi/full/10.1128/aac.01506-19 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 91.0 |
no [IC50 >1000 uM] | |||
Page: 34 | 85 |
no | |||
Page: 34 | 84 |
no | |||
Page: 34 | 84 | 128 |
no | |||
Page: 34 | 84 | 127 |
no | |||
Page: 34 | 84 |
no | |||
Page: 34 | 84 | 127 |
no | |||
Page: 34 | 84 | 128 |
no | |||
Page: 34 | 84 | 127 |
no | |||
Page: 34 | 84 | 128 |
no | |||
Page: 34 | 84 | 128 |
no | |||
Page: 34 | 84 | 127 |
no | |||
Page: 34 | 84 |
no | |||
Page: 34 | 84 | 127 | 128 |
no | |||
Page: 127 | 128 |
no | |||
Page: 34 | 85 |
no | |||
Page: 34 | 85 |
no | |||
Page: 34 | 85 |
no | |||
Page: 34 | 85 |
no | |||
Page: 34 | 85 | 129 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 84 | 85 |
no | |||
Page: 33.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 91.0 |
||||
Page: 91.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
Sources: https://pubmed.ncbi.nlm.nih.gov/28665414
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
Edited
Tue Apr 01 21:23:18 GMT 2025
by
admin
on
Tue Apr 01 21:23:18 GMT 2025
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Record UNII |
F78MDZ9CW9
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Record Status |
Validated (UNII)
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Record Version |
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100000183473
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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