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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key JHFNIHVVXRKLEF-DCZLAGFPSA-N
References
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]