Compound ID | 93

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Ceftolozane + tazobactam (Zerbaxa)

Synonym(s): Ceftolozane sulfate  |  tazobactam sodium

Class: Beta-lactam + beta-lactamase inhibitor

Agent Type: Semisynthetic; Small molecule; Direct acting; Indirect acting; Antibiotic adjuvant;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Ceftolozane inhibits PBP3-mediated bacterial cell wall synthesis; tazobactam irreversibly inhibits selected class A β-lactamases and protects ceftolozane from enzymatic degradation
Target Pathogen: Escherichia coli, Klebsiella pneumoniae, Klebsiella oxytoca, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Serratia marcescens, and Haemophilus influenzae (approved indications), with additional activity against many ESBL-producing Enterobacterales
Combined with other compounds: Yes
Description: Ceftolozane is a novel antipseudomonal fourth-generation cephalosporin combined with tazobactam, a penicillanic acid sulfone β-lactamase inhibitor
Institute where first reported: Cubist Pharmaceuticals; Merck & Co; Astellas Pharma
Year first mentioned: 2012
Highest development stage: Approved by FDA in 2014
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 966.99
Iso. SMILES: C[C@@]1([C@@H](N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.CC(C)(C(=O)O)O/N=C(\C1=NSC(=N1)N)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)[O-]
InChI Key: GRHWKSLBMDQBQW-KZVOOCJBSA-N
Can. SMILES: CC(C)(C(=O)O)O/N=C(\C1=NSC(=N1)N)/C(=O)N[C@@H]2C(=O)N3C(=C(C[N+]4=CC(=C(N)N4C)NC(=O)NCCN)CS[C@H]23)C(=O)[O-].C[C@]1(CN2C=CN=N2)[C@H](C(=O)O)N3C(=O)CC3S1(=O)=O
InChI: InChI=1S/C23H30N12O8S2.C10H12N4O5S/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24;1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42);2-3,7-8H,4-5H2,1H3,(H,16,17)/b31-11+;/t12-,18-;7?,8-,10-/m10/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/86291594
Guide to Pharmacology: ceftolozane
Citations:
  • http://aac.asm.org/content/56/6/3086.long
  • http://aac.asm.org/content/57/12/6305.full
  • http://aac.asm.org/content/57/6/2809.full
    • Patent: US20150045336A1

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