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) antibiotic. It has replaced methicillin in clinical use.
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
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
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
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