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 antibiotic that has broad spectrum activity against Gram positive and Gram negative bacteria. The active Ingredient in medications is cefotaxime sodium.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). 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
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
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UniChem Compound Search for chemical match using the InChIKey GPRBEKHLDVQUJE-QSWIMTSFSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPRBEKHLDVQUJE-QSWIMTSFSA-N