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ceftizoxime   Click here for help

GtoPdb Ligand ID: 10785

Synonyms: Cefizox® | compound 22 {PMID: 2342058] | Epocelin® | FK-749 | FK749 | FR-13749 | FR13749 | SK&F 88373-Z
Approved drug
ceftizoxime is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: Ceftizoxime is a semisynthetic, broad-spectrum, β-lactamase-resistant, parenterally administered third-generation cephalosporin antibacterial with Gram +ve and Gram -ve activity. Unlike other third-generation cephalosporins, ceftizoxime's C-3 side chain has been removed to prevent deactivation by hydrolytic enzymes.

ceftizoxime is commercially available from our sponsors

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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 200.75
Molecular weight 383.04
XLogP -2.27
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
InChI InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
InChI Key NNULBSISHYWZJU-LLKWHZGFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Blaszczak LC, Brown RF, Cook GK, Hornback WJ, Hoying RC, Indelicato JM, Jordan CL, Katner AS, Kinnick MD, McDonald 3rd JH et al.. (1990)
Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins.
J Med Chem, 33 (6): 1656-62. [PMID:2342058]
2. Cui L, Neoh HM, Shoji M, Hiramatsu K. (2009)
Contribution of vraSR and graSR point mutations to vancomycin resistance in vancomycin-intermediate Staphylococcus aureus.
Antimicrob Agents Chemother, 53 (3): 1231-4. [PMID:19124662]