Oxacillin

Class: Beta-lactam (isoxazolylpenicillin)

Spectrum of activity:	Gram-positive
Details of activity:	Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria, especially staphylococci including penicillinase producing strains
Description:	Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Parenteral application. It has replaced methicillin in clinical use
Year first mentioned:	1960
Development status:	Approved, off-patent

Chemical structure(s):
Canonical SMILES:	CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@@H]3C(=O)N4[C@@H](C(=O)O)C(C)(C)S[C@H]34
Isomeric SMILES:	CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
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
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/6196

External links:
Guide to Pharmacology:	oxacillin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/4919148/
Citations:	https://pubmed.ncbi.nlm.nih.gov/28893360/ https://www.sciencedirect.com/science/article/pii/S2213716520300631?via%3Dihub