Compound ID | 2700

Update compound information

Quinacillin

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against penicillin-resistant and -susceptible Staphylococcus aureus (resistant to penicillinase activity)
Description: Semisynthetic compound prepared from 6-aminopenicillanic acid (6-APA) and quinoxaline-2,3-dicarboxylic anhydride; a derivative of penicillin; effective in treating staphylococcal infection when administered parenterally; poorly absorbed orally; successful clinical trials (1966) but current status of drug unknown
Institute where first reported: Boots Pure Drug Co., Nottingham
Year first mentioned: 1963
Development status: Experimental
Chemical structure(s):
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Molecular weight: 416.41
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=NC4=CC=CC=C4N=C3C(=O)O)C(=O)O)C
InChI Key: GPMSLJIYNWBYEL-TYNCELHUSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)C3=C(C(=O)O)N=C4C=CC=CC4=N3
InChI: InChI=1S/C18H16N4O6S/c1-18(2)12(17(27)28)22-14(24)11(15(22)29-18)21-13(23)9-10(16(25)26)20-8-6-4-3-5-7(8)19-9/h3-6,11-12,15H,1-2H3,(H,21,23)(H,25,26)(H,27,28)/t11-,12+,15-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/92894
Citations:
  • https://journals.sagepub.com/doi/10.1177/003693306601100505
  • https://karger.com/che/article-pdf/16/3/183/2388388/000220726.pdf
  • https://www.nature.com/articles/2021217a0
  • https://www.nature.com/articles/199354a0

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