enmetazobactam   Click here for help

GtoPdb Ligand ID: 12188

Synonyms: AAI101 | OCID-5090
Compound class: Synthetic organic
Comment: Enmetazobactam is an extended-spectrum β-lactamase inhibitor. It is an N-methylated tazobactam derivative, under clinical development for use alongside β-lactam-containing antibacterial compounds to reduce their lactamase-induced degradation.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 124.66
Molecular weight 314.07
XLogP -1.75
No. Lipinski's rules broken 0
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Canonical SMILES [O-]C(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)[C@@]1(C)Cn1cc[n+](n1)C
Isomeric SMILES C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])Cn1cc[n+](n1)C
InChI InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1
1. Kaye KS, Belley A, Barth P, Lahlou O, Knechtle P, Motta P, Velicitat P. (2022)
Effect of Cefepime/Enmetazobactam vs Piperacillin/Tazobactam on Clinical Cure and Microbiological Eradication in Patients With Complicated Urinary Tract Infection or Acute Pyelonephritis: A Randomized Clinical Trial.
JAMA, 328 (13): 1304-1314. [PMID:36194218]
2. Papp-Wallace KM, Bethel CR, Caillon J, Barnes MD, Potel G, Bajaksouzian S, Rutter JD, Reghal A, Shapiro S, Taracila MA et al.. (2019)
Beyond Piperacillin-Tazobactam: Cefepime and AAI101 as a Potent β-Lactam-β-Lactamase Inhibitor Combination.
Antimicrob Agents Chemother, 63 (5). [PMID:30858223]