Compound ID | 1936

Update compound information

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
Highest developmental phase: Approved by FDA in 1989
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 401.44
Iso. 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 Key: UWYHMGVUTGAWSP-JKIFEVAISA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6196
Guide to Pharmacology: oxacillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/28893360/
  • https://www.sciencedirect.com/science/article/pii/S2213716520300631?via%3Dihub
  • https://pubmed.ncbi.nlm.nih.gov/4919148/

    • AntibioticDB is supported by GARDP.

    If you have feedback, experience problems, or are interested in a collaboration, please contact us. | Terms and conditions

    The content of this site is intended for educational and scientific research purposes only and not as a source of medical advice or consultation.