Quinacillin

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Quinacillin

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Quinacillin

UNII-83NB50X92M

Cas 1596-63-0

83NB50X92M

Quinacilina

MW 416.4 g/mol, MF C18H16N4O6S

(2S,5R,6R)-6-[(3-carboxyquinoxaline-2-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(3-carboxy-2-quinoxalinecarboxamido)-3,3-dimethyl-7-oxo- (7CI,8CI)
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(3-carboxy-2-quinoxalinyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
  • (2S,5R,6R)-6-[[(3-Carboxy-2-quinoxalinyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 3-Carboxy-2-quinoxalinylpenicillanic acid
  • 3-Carboxy-2-quinoxalinylpenicillin
  • 6-(3-Carboxy-2-quinoxalinecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • Penicillin, (3-carboxy-2-quinoxalinyl)-
CAS Registry Number: 1596-63-0
CAS Name: (2S,5R,6R)-6-[[(3-Carboxy-2-quinoxalinyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 3-carboxy-2-quinoxalinylpenicillin
Molecular Formula: C18H16N4O6S
Molecular Weight: 416.41
Percent Composition: C 51.92%, H 3.87%, N 13.45%, O 23.05%, S 7.70%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepd by condensation of quinoxaline-2,3-dicarboxylic anhydride with 6-aminopenicillanic acid: Richards et al., Nature 199, 354 (1963).
Derivative Type: Disodium salt
CAS Registry Number: 985-32-0
Molecular Formula: C18H14N4Na2O6S
Molecular Weight: 460.37
Percent Composition: C 46.96%, H 3.07%, N 12.17%, Na 9.99%, O 20.85%, S 6.97%
Properties: Crystals, dec 261-262°. [a]D23 +183.5° (water). Very hygroscopic. uv max (containing 9.2% water): 242, 326 nm (e32,100; 7280). Acquires a bright yellow color on exposure to strong sunlight but is stable at 100° for at least 3 months. Freely sol in water; a 25% aq soln is stable for 2 months at 0°. Antimicrobial activity is highest against Staphylococcus aureus.
Optical Rotation: [a]D23 +183.5° (water)
Absorption maximum: uv max (containing 9.2% water): 242, 326 nm (e 32,100; 7280)
Quinacillin bistriethylammonium.png
cas 13549-27-4
Derivative Type: Bistriethylammonium salt monohydrate
Molecular Formula: C30H46N6O6S.H2O
Molecular Weight: 636.80
Percent Composition: C 56.58%, H 7.60%, N 13.20%, O 17.59%, S 5.04%
Properties: Crystals from acetone, dec 135-137°. [a]D20 +142° (c = 0.376 in water).
Optical Rotation: [a]D20 +142° (c = 0.376 in water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
Quinacillin is a semisynthetic penicillase-resistant penicillin with antibacterial activity. Quinacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.
PATENTS
GB 867890
GB 967890
JP 47026513
DE 2161659
WO 2014111957
IN 2013MU00181
US 20150328323
PAPER
//////Quinacillin
CC1(C(N2C(S1)C(C2=O)NC(=O)C3=NC4=CC=CC=C4N=C3C(=O)O)C(=O)O)C
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