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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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
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)
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