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cefmenoxime   Click here for help

GtoPdb Ligand ID: 12024

Synonyms: A-50912 | Abbott 50192 | Bestron® | Cefmax® | SCE-1365
Approved drug
cefmenoxime is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: Cefmenoxime is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds [1]. It has broad-spectrum activity against both Gram-positive and Gram-negative bacteria and is resistant to hydrolysis by β-lactamases.
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 11
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 269.65
Molecular weight 511.05
XLogP -2.26
No. Lipinski's rules broken 1

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(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)/c1csc(n1)N
Isomeric SMILES Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/c2csc(n2)N)SC1)C(=O)O
InChI InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1
InChI Key HJJDBAOLQAWBMH-YCRCPZNHSA-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. US FDA (1987)
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]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
4930 cefmenoxime
Synonyms Click here for help
A-50912 | Abbott 50192 | Bestron® | Cefmax® | SCE-1365
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefmenoxime
Other databases
CAS Registry No. 65085-01-0 (source: Scifinder)
ChEBI CHEBI:55490
ChEMBL Ligand CHEMBL1201224
DrugBank Ligand DB00267
GtoPdb PubChem SID 464244165
PubChem CID 9570757
Search Google for chemical match using the InChIKey HJJDBAOLQAWBMH-YCRCPZNHSA-N
Search Google for chemicals with the same backbone HJJDBAOLQAWBMH
Search PubMed clinical trials cefmenoxime
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Search PubMed titles/abstracts cefmenoxime
UniChem Compound Search for chemical match using the InChIKey HJJDBAOLQAWBMH-YCRCPZNHSA-N
UniChem Connectivity Search for chemical match using the InChIKey HJJDBAOLQAWBMH-YCRCPZNHSA-N