oxacillin   Click here for help

GtoPdb Ligand ID: 10943

Synonyms: Bactocill®
Approved drug
oxacillin is an approved drug (FDA (1971))
Compound class: Synthetic organic
Comment: Oxacillin is a semi-synthetic penicillinase-resistant and acid-stable, a parenteral β-lactam (penicillin) antibacterial. It has replaced methicillin in clinical use.
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 2
Rotatable bonds 5
Topological polar surface area 138.04
Molecular weight 401.1
XLogP 2.41
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@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1
Isomeric SMILES OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1
InChI InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
InChI Key UWYHMGVUTGAWSP-JKIFEVAISA-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 (1971))
Approved drug? Yes. FDA (1971)
IUPAC Name Click here for help
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
1372 oxacillin
Synonyms Click here for help
Bactocill®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Oxacillin
Other databases
BindingDB Ligand 50350483
CAS Registry No. 66-79-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL819
DrugBank Ligand DB00713
DrugCentral Ligand 2006
GtoPdb PubChem SID 405560384
PubChem CID 6196
Search Google for chemical match using the InChIKey UWYHMGVUTGAWSP-JKIFEVAISA-N
Search Google for chemicals with the same backbone UWYHMGVUTGAWSP
Search PubMed clinical trials oxacillin
Search PubMed titles oxacillin
Search PubMed titles/abstracts oxacillin
UniChem Compound Search for chemical match using the InChIKey UWYHMGVUTGAWSP-JKIFEVAISA-N
UniChem Connectivity Search for chemical match using the InChIKey UWYHMGVUTGAWSP-JKIFEVAISA-N