cefamandole   Click here for help

GtoPdb Ligand ID: 12210

Synonyms: cephamandole
Approved drug PDB Ligand
cefamandole is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Cefamandole is a semisynthetic, second generation cephalosporin belonging to the β-lactam class of antibacterial compounds [1]. It has broad-spectrum activity and is β-lactamase-resistant. It is administered parenterally as the prodrug cefamandole nafate.
Because of its inhibitory activity towards human aldehyde dehydrogenase, cefamandole produces an effect to ethanol similar to that produced by disulfiram (Antabuse®).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 201.14
Molecular weight 462.51
XLogP 0.2
No. Lipinski's rules broken 0
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Canonical SMILES O[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)c1ccccc1
Isomeric SMILES Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](c2ccccc2)O)SC1)C(=O)O
InChI InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1978))
IUPAC Name Click here for help
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-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
3329 cefamandole
Synonyms Click here for help
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefamandole
Other databases
CAS Registry No. 34444-01-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1146
DrugBank Ligand DB01326
DrugCentral Ligand 527
GtoPdb PubChem SID 472319330
PubChem CID 456255
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UniChem Compound Search for chemical match using the InChIKey OLVCFLKTBJRLHI-AXAPSJFSSA-N
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