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 antibiotic 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.
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1983))
Withdrawn drug? Yes
Prodrug ceftizoxime alapivoxil
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4743 ceftizoxime
Synonyms Click here for help
Cefizox® | compound 22 {PMID: 2342058] | Epocelin® | FK-749 | FK749 | FR-13749 | FR13749 | SK&F 88373-Z
Database Links Click here for help
BindingDB Ligand 237182
CAS Registry No. 68401-81-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL528
DrugCentral Ligand 563
GtoPdb PubChem SID 405560226
PubChem CID 6533629
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UniChem Compound Search for chemical match using the InChIKey NNULBSISHYWZJU-LLKWHZGFSA-N
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