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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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 8
Topological polar surface area 201.14
Molecular weight 462.51
XLogP 0.2
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 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
InChI Key OLVCFLKTBJRLHI-AXAPSJFSSA-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 (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
cephamandole
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)
ChEBI CHEBI:3480
ChEMBL Ligand CHEMBL1146
DrugBank Ligand DB01326
DrugCentral Ligand 527
GtoPdb PubChem SID 472319330
PubChem CID 456255
RCSB PDB Ligand SMX
Search Google for chemical match using the InChIKey OLVCFLKTBJRLHI-AXAPSJFSSA-N
Search Google for chemicals with the same backbone OLVCFLKTBJRLHI
Search PubMed clinical trials cefamandole
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Search PubMed titles/abstracts cefamandole
UniChem Compound Search for chemical match using the InChIKey OLVCFLKTBJRLHI-AXAPSJFSSA-N
UniChem Connectivity Search for chemical match using the InChIKey OLVCFLKTBJRLHI-AXAPSJFSSA-N