ceftibuten   Click here for help

GtoPdb Ligand ID: 12029

Synonyms: 7432-S | Cedax® | SCH 39720
Approved drug
ceftibuten is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Ceftibuten is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds [1].
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 10
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 216.46
Molecular weight 410.04
XLogP -2.77
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 OC(=O)C/C=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O)/c1csc(n1)N
Isomeric SMILES C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C\CC(=O)O)/c1csc(n1)N)C(=O)O
InChI InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
InChI Key UNJFKXSSGBWRBZ-BJCIPQKHSA-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
Approved drug? Yes (FDA (1995))
Approved drug? Yes. FDA (1995)
IUPAC Name Click here for help
(6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]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
6335 ceftibuten
Synonyms Click here for help
7432-S | Cedax® | SCH 39720
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ceftibuten
Other databases
CAS Registry No. 97519-39-6 (source: Scifinder)
ChEBI CHEBI:3510
ChEMBL Ligand CHEMBL1605
DrugBank Ligand DB01415
DrugCentral Ligand 562
GtoPdb PubChem SID 464244170
PubChem CID 5282242
Search Google for chemical match using the InChIKey UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Search Google for chemicals with the same backbone UNJFKXSSGBWRBZ
Search PubMed clinical trials ceftibuten
Search PubMed titles ceftibuten
Search PubMed titles/abstracts ceftibuten
UniChem Compound Search for chemical match using the InChIKey UNJFKXSSGBWRBZ-BJCIPQKHSA-N
UniChem Connectivity Search for chemical match using the InChIKey UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Wikipedia Ceftibuten