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azlocillin   Click here for help

GtoPdb Ligand ID: 12260

Synonyms: Azlin® | BAY-E-6905
Approved drug
azlocillin is an approved drug (FDA)
Compound class: Synthetic organic
Comment: Azlocillin is a semisynthetic penicillin derivative belonging to the β-lactam class of antibacterial compounds.
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 4
Rotatable bonds 8
Topological polar surface area 173.45
Molecular weight 461.14
XLogP 0.65
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 O=C([C@@H](c1ccccc1)NC(=O)N1CCNC1=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)NC(=O)N1CCNC1=O)C(=O)O)C
InChI InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChI Key JTWOMNBEOCYFNV-NFFDBFGFSA-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 (0)
IUPAC Name Click here for help
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4011 azlocillin
Synonyms Click here for help
Azlin® | BAY-E-6905
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Azlocillin
Other databases
CAS Registry No. 37091-66-0 (source: Scifinder)
ChEBI CHEBI:2956
ChEMBL Ligand CHEMBL1537
DrugBank Ligand DB01061
DrugCentral Ligand 277
GtoPdb PubChem SID 473153848
PubChem CID 6479523
Search Google for chemical match using the InChIKey JTWOMNBEOCYFNV-NFFDBFGFSA-N
Search Google for chemicals with the same backbone JTWOMNBEOCYFNV
Search PubMed clinical trials azlocillin
Search PubMed titles azlocillin
Search PubMed titles/abstracts azlocillin
UniChem Compound Search for chemical match using the InChIKey JTWOMNBEOCYFNV-NFFDBFGFSA-N
UniChem Connectivity Search for chemical match using the InChIKey JTWOMNBEOCYFNV-NFFDBFGFSA-N