Compound ID | 1954

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Sulbactam plus durlobactam (Xacduro)

Synonym(s): ETX2514SUL

Class: Beta-lactamase inhibitor (penicillanic acid sulfone)

Spectrum of activity: Gram-negative
Details of activity: Sulbactam binds to Penicillin Binding Protein 1 and 3 (PBP 1, 3) of Acinetobacter but is hydrolysed by OXA beta-lactamases of Acinetobacter. Durlobactam inhibits class D beta-lactamases (OXA beta-lactamases) in Acinetobacter.
Combined with other compounds: Yes
Description: Combination of a semisynthetic penicillanic acid sulfone beta-lactamase inhibitor with Penicillin Binding Protein binding activity in Acinetobacter and a synthetic non-β-lactam diazabicyclooctane (DBO) β-lactamase inhibitor
Institute where first reported: Entasis Therapeutics, Innoviva
Year first mentioned: 2017
Highest developmental phase: Approved by FDA in 2023
Development status: Approved
Chemical structure(s):
Sulbactam
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Molecular weight: 233.24
Iso. SMILES: CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C
InChI Key: FKENQMMABCRJMK-RITPCOANSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O
InChI: InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
Durlobactam
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Molecular weight: 277.26
Iso. SMILES: CC1=C[C@@H]2CN([C@@H]1C(=O)N)C(=O)N2OS(=O)(=O)O
InChI Key: BISPBXFUKNXOQY-RITPCOANSA-N
Can. SMILES: CC1=C[C@@H]2CN([C@@H]1C(=O)N)C(=O)N2OS(=O)(=O)O
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/130313
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/89851852
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/28835096/
  • https://www.nature.com/articles/d41573-023-00096-8
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6414696/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4325763/

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