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Cas 1596-63-0



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.
GB 867890
GB 967890
JP 47026513
DE 2161659
WO 2014111957
IN 2013MU00181
US 20150328323

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DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, CLEANCHEM LABS as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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