Enmetazobactam

Synonym(s): AAI101  |  OCID 5090

Class: Beta-lactamase inhibitor (penicillanic acid sulfone)

Details of activity:	Binds irreversibly to beta-lactamases, mainly class A enzymes. No intrinsic antibacterial activity
Combined with other compounds:	Yes
Description:	Semisynthetic, derived from tazobactam, similar inhibition profiles to tazobactam. Only available as a combination product, fixed combination with cefepime
Institute where first reported:	Orchid, Allecra
Year first mentioned:	1998
Highest developmental phase:	Approved by FDA in 2024
Development status:	Approved

Chemical structure(s):
Canonical SMILES:	C[C@]1(CN2C=C[N+](=N2)C)[C@H](C(=O)[O-])N3C(=O)C[C@H]3S1(=O)=O
Isomeric SMILES:	C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])CN3C=C[N+](=N3)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
InChI Key:	HFZITXBUTWITPT-YWVKMMECSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/23653540

External links:
Guide to Pharmacology:	enmetazobactam
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6496078/
Citations:	https://www.escmid.org/fileadmin/src/media/PDFs/Abstractbook2020_05.05.2020_Part5.pdf#page=131 https://www.pnas.org/doi/10.1073/pnas.2117310119