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Avibactam

Avibactam Pharmaceutical Intermediates CAS NO 1192500-31-4 Cas 1192491-61-4

Clinical data
Trade names	Avycaz (formulated with ceftazidime)
License data	EU EMA: by INN
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	IV
ATC code	None
Legal status
Legal status	US: ?-only
Pharmacokinetic data
Bioavailability	100% (intravenous)
Protein binding	5.7–8.2%[1]
Metabolism	Nil
Onset of action	Increases in proportion to dose
Excretion	Renal (97%)
Identifiers
IUPAC name[hide] [(2S,5R)-2-Carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
CAS Number	1192500-31-4
PubChem CID	9835049
ChemSpider	8010770
KEGG	D10340
ChEBI	CHEBI:85984 [Yes]
ChEMBL	CHEMBL1689063
Chemical and physical data
Formula	C7H11N3O6S
Molar mass	265.24 g/mol
3D model (JSmol)	Interactive image
SMILES[hide] [C@]12C[N@]([C@@H](CC1)C(N)=O)C(=O)N2OS(O)(=O)=O
InChI[hide] InChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1 Key:NDCUAPJVLWFHHB-UHNVWZDZSA-N

Avibactam is a non-β-lactam β-lactamase inhibitor[2] developed by Actavis (now [Teva]) jointly with AstraZeneca. A new drug application for avibactam in combination with ceftazidime (branded as Avycaz) was approved by the FDA on February 25, 2015, for treating complicated urinary tract (cUTI) and complicated intra-abdominal infections (cIAI) caused by antibiotic resistant-pathogens, including those caused by multi-drug resistant Gram-negative bacterial pathogens.

Increasing resistance to cephalosporins among Gram-(−) bacterial pathogens, especially among hospital-acquired infections, results in part from the production of β-lactamase enzymes that deactivate these antibiotics. While the co-administration of a β-lactamase inhibitor can restore antibacterial activity to the cephalosporin, previously approved β-lactamase inhibitors such as tazobactam andclavulanic acid do not inhibit important classes of β-lactamases, including Klebsiella pneumoniae carbapenemases (KPCs), New Delhi metallo-β-lactamase 1 (NDM-1), and AmpC-type β-lactamases. Whilst avibactam inhibits class A (KPCs, CTX-M, TEM, SHV), class C (AmpC), and, some, class D serine β-lactamases (such as OXA-23, OXA-48), it has been reported to be a poor substrate/weak inhibitor of class B metallo-β-lactamases, such as VIM-2, VIM-4, SPM-1, BcII, NDM-1, Fez-1.

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