Quinacillin

Quinacillin is a penicillin antibiotic which can reversibly deactivate beta-lactamase enzymes.[1] Activity against Staphylococcus aureus is much more potent than against other Gram-positive organisms.[2]

Quinacillin
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 3-{[(2S,5R,6R)-2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]carbamoyl}-2-quinoxalinecarboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.014.984
Chemical and physical data
FormulaC18H16N4O6S
Molar mass416.41 g·mol−1
3D model (JSmol)
SMILES
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)c3c(nc4ccccc4n3)C(=O)O)C(=O)O)C
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
  • Key:GPMSLJIYNWBYEL-TYNCELHUSA-N

References
  1. Persaud KC, Pain RH, Virden R (August 1986). "Reversible deactivation of beta-lactamase by quinacillin. Extent of the conformational change in the isolated transitory complex". The Biochemical Journal. 237 (3): 723–30. doi:10.1042/bj2370723. PMC 1147050. PMID 3492197.
  2. Hugo WB, Stretton RG (June 1964). "Action of Quinacillin on Staphylococcus aureus". Nature. 202 (4938): 1217. Bibcode:1964Natur.202.1217H. doi:10.1038/2021217a0. PMID 14217514. S2CID 4198059.
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