sulbactam   Click here for help

GtoPdb Ligand ID: 10769

Synonyms: Betamaze | CP-45,899 | CP-45899
Approved drug PDB Ligand
sulbactam is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Sulbactam is a β-lactamase inhibitor that is used to limit degradation of β-lactam antibacterials. Its synergy with β-lactam antibacterials against some multiply drug-resistant Enterobacteriaceae and Pseudomonas species is reported to be inconsistent, likely as it cannot inhibit the AmpC cephalosporinase expressed by these species [1].

sulbactam 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 6
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 100.13
Molecular weight 233.04
XLogP -1.13
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 OC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C
Isomeric SMILES OC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C
InChI InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
InChI Key FKENQMMABCRJMK-RITPCOANSA-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 (1986)
Prodrug sultamicillin
IUPAC Name Click here for help
(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4845 sulbactam
Synonyms Click here for help
Betamaze | CP-45,899 | CP-45899
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulbactam | Sulbactam/ carbenicillin
Other databases
CAS Registry No. 68373-14-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL403
DrugCentral Ligand 2492
GtoPdb PubChem SID 405560210
PubChem CID 130313
RCSB PDB Ligand 0RN
Search Google for chemical match using the InChIKey FKENQMMABCRJMK-RITPCOANSA-N
Search Google for chemicals with the same backbone FKENQMMABCRJMK
Search PubMed clinical trials sulbactam
Search PubMed titles sulbactam
Search PubMed titles/abstracts sulbactam
UniChem Compound Search for chemical match using the InChIKey FKENQMMABCRJMK-RITPCOANSA-N
UniChem Connectivity Search for chemical match using the InChIKey FKENQMMABCRJMK-RITPCOANSA-N

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MedChemExpress
Sulbactam (links to external site)
Cat. No. HY-B0334