ceftolozane   Click here for help

GtoPdb Ligand ID: 10788

Synonyms: CXA-101 | CXA101 | FR-264205 | FR264205 | Zerbaxa® (ceftolozane + tazobactam)
Approved drug
ceftolozane is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Ceftolozane is a semi-synthetic, broad-spectrum, fifth-generation cephalosporin antibacterial with activity against certain Gram-negative (e.g. Pseudomonas spp.) and Gram-positive bacteria [6].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 7
Rotatable bonds 15
Topological polar surface area 355.75
Molecular weight 666.18
XLogP -6.08
No. Lipinski's rules broken 3
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Canonical SMILES NCCNC(=O)Nc1c[n+](n(c1N)C)CC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)/C(=N\OC(C(=O)O)(C)C)/c1nsc(n1)N
Isomeric SMILES NCCNC(=O)Nc1c[n+](n(c1N)C)CC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)/C(=N\OC(C(=O)O)(C)C)/c1nsc(n1)N
InChI InChI=1S/C23H30N12O8S2/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/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1
1. Cluck D, Lewis P, Stayer B, Spivey J, Moorman J. (2015)
Ceftolozane-tazobactam: A new-generation cephalosporin.
Am J Health Syst Pharm, 72 (24): 2135-46. [PMID:26637512]
2. Gallagher JC, Satlin MJ, Elabor A, Saraiya N, McCreary EK, Molnar E, El-Beyrouty C, Jones BM, Dixit D, Heil EL et al.. (2018)
Ceftolozane-Tazobactam for the Treatment of Multidrug-Resistant Pseudomonas aeruginosa Infections: A Multicenter Study.
Open Forum Infect Dis, 5 (11): ofy280. [PMID:30488041]
3. Giacobbe DR, Bassetti M, De Rosa FG, Del Bono V, Grossi PA, Menichetti F, Pea F, Rossolini GM, Tumbarello M, Viale P et al.. (2018)
Ceftolozane/tazobactam: place in therapy.
Expert Rev Anti Infect Ther, 16 (4): 307-320. [PMID:29493397]
4. Haidar G, Philips NJ, Shields RK, Snyder D, Cheng S, Potoski BA, Doi Y, Hao B, Press EG, Cooper VS et al.. (2017)
Ceftolozane-Tazobactam for the Treatment of Multidrug-Resistant Pseudomonas aeruginosa Infections: Clinical Effectiveness and Evolution of Resistance.
Clin Infect Dis, 65 (1): 110-120. [PMID:29017262]
5. Moyá B, Zamorano L, Juan C, Ge Y, Oliver A. (2010)
Affinity of the new cephalosporin CXA-101 to penicillin-binding proteins of Pseudomonas aeruginosa.
Antimicrob Agents Chemother, 54 (9): 3933-7. [PMID:20547785]
6. Zhanel GG, Chung P, Adam H, Zelenitsky S, Denisuik A, Schweizer F, Lagacé-Wiens PR, Rubinstein E, Gin AS, Walkty A et al.. (2014)
Ceftolozane/tazobactam: a novel cephalosporin/β-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli.
Drugs, 74 (1): 31-51. [PMID:24352909]