cefotaxime   Click here for help

GtoPdb Ligand ID: 10893

Synonyms: Claforan® | Ru-24756
Approved drug PDB Ligand
cefotaxime is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: Cefotaxime is a third generation semisynthetic cephalosporin antibacterial that has broad spectrum activity against Gram positive and Gram negative bacteria. The active Ingredient in medications is cefotaxime sodium.

cefotaxime 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 9
Topological polar surface area 227.05
Molecular weight 455.06
XLogP -2.71
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]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C
InChI InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChI Key GPRBEKHLDVQUJE-QSWIMTSFSA-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 (1981))
Approved drug? Yes. FDA (1981)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(6R,7R)-3-(acetyloxymethyl)-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
4504 cefotaxime
Synonyms Click here for help
Claforan® | Ru-24756
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefotaxime | Ceftriaxone and Cefotaxime
Other databases
CAS Registry No. 63527-52-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL1730
DrugCentral Ligand 546
GtoPdb PubChem SID 405560334
PubChem CID 5742673
RCSB PDB Ligand CE3
Search Google for chemical match using the InChIKey GPRBEKHLDVQUJE-QSWIMTSFSA-N
Search Google for chemicals with the same backbone GPRBEKHLDVQUJE
Search PubMed clinical trials cefotaxime
Search PubMed titles cefotaxime
Search PubMed titles/abstracts cefotaxime
UniChem Compound Search for chemical match using the InChIKey GPRBEKHLDVQUJE-QSWIMTSFSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPRBEKHLDVQUJE-QSWIMTSFSA-N

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MedChemExpress
Cefotaxime (links to external site)
Cat. No. HY-A0088A