Chemistry:Quinacillin

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	1596-63-0;
PubChem CID	92894;
ChemSpider	83858;
UNII	83NB50X92M;
ChEMBL	ChEMBL2104733;
Chemical and physical data
Formula	C18H16N4O6S
Molar mass	416.41 g·mol−1
3D model (JSmol)	Interactive image;
	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;

Short description: Beta-lactam antibiotic

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]

References

↑ "Reversible deactivation of beta-lactamase by quinacillin. Extent of the conformational change in the isolated transitory complex". The Biochemical Journal 237 (3): 723–30. August 1986. doi:10.1042/bj2370723. PMID 3492197.
↑ "Action of Quinacillin on Staphylococcus aureus". Nature 202 (4938): 1217. June 1964. doi:10.1038/2021217a0. PMID 14217514. Bibcode: 1964Natur.202.1217H.

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[1] "Reversible deactivation of beta-lactamase by quinacillin. Extent of the conformational change in the isolated transitory complex". The Biochemical Journal 237 (3): 723–30. August 1986. doi:10.1042/bj2370723. PMID 3492197.

[2] "Action of Quinacillin on Staphylococcus aureus". Nature 202 (4938): 1217. June 1964. doi:10.1038/2021217a0. PMID 14217514. Bibcode: 1964Natur.202.1217H.

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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	1596-63-0
PubChem CID	92894
ChemSpider	83858
UNII	83NB50X92M
ChEMBL	ChEMBL2104733
Chemical and physical data
Formula	C₁₈H₁₆N₄O₆S
Molar mass	416.41 g·mol⁻¹
3D model (JSmol)	Interactive image
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

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