ceftiofur   Click here for help

GtoPdb Ligand ID: 13653

Synonyms: Naxcel® (veterinary)
Compound class: Synthetic organic
Comment: Ceftiofur is a third generation cephalosporin belonging to the β-lactam class of antibacterial compounds. It has activity against Gram-positive and Gram-negative bacteria and was developed for use in veterinary medicine [1].

ceftiofur 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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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 10
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 248.88
Molecular weight 523.57
XLogP -2.1
No. Lipinski's rules broken 1

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(/C1=CSC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=C(CS[C@H]23)CSC(=O)C4=CC=CO4)C(=O)O
Isomeric SMILES CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O
InChI InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1
InChI Key ZBHXIWJRIFEVQY-IHMPYVIRSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-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
5703 ceftiofur
Synonyms Click here for help
Naxcel® (veterinary)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ceftiofur
Other databases
BindingDB Ligand 50103524
CAS Registry No. 80370-57-6 (source: Scifinder)
ChEMBL Ligand CHEMBL222913
DrugBank Ligand DB11485
DrugCentral Ligand 5663
GtoPdb PubChem SID 507750287
PubChem CID 6328657
Search Google for chemical match using the InChIKey ZBHXIWJRIFEVQY-IHMPYVIRSA-N
Search Google for chemicals with the same backbone ZBHXIWJRIFEVQY
Search PubMed clinical trials ceftiofur
Search PubMed titles ceftiofur
Search PubMed titles/abstracts ceftiofur
UniChem Compound Search for chemical match using the InChIKey ZBHXIWJRIFEVQY-IHMPYVIRSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZBHXIWJRIFEVQY-IHMPYVIRSA-N

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MedChemExpress
Ceftiofur (links to external site)
Cat. No. HY-N7102