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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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
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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
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Summary of Clinical Use Click here for help
Oxacillin is used to treat moderate-to-severe, penicillin-resistant staphylococcal infections. In the US oxacillin or nafcillin are recommended as the first-line treatment of choice for staphylococcal endocarditis (in patients with no artificial heart valves). Oxacillin-resistant Staphylococcus aureus (ORSA) can be treated with vancomycin.
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