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CAS 50846-45-2

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Bacmecillinam

Description:
Bacmecillinam is a semi-synthetic antibiotic belonging to the penicillin class, primarily used for its antibacterial properties. It is characterized by its ability to inhibit bacterial cell wall synthesis, making it effective against a range of Gram-negative bacteria. Bacmecillinam is particularly noted for its stability in the presence of certain beta-lactamases, enzymes produced by some bacteria that confer resistance to other penicillins. The compound is typically administered orally and is known for its favorable pharmacokinetic profile, which allows for effective absorption and distribution in the body. Its mechanism of action involves binding to penicillin-binding proteins (PBPs), disrupting the cross-linking of peptidoglycan layers in bacterial cell walls, ultimately leading to cell lysis and death. Bacmecillinam is often used in the treatment of urinary tract infections and other infections caused by susceptible organisms. As with other antibiotics, it is essential to use Bacmecillinam judiciously to minimize the development of antibiotic resistance.
Formula:C20H31N3O6S
InChI:InChI=1/C20H31N3O6S/c1-5-27-19(26)29-13(2)28-18(25)15-20(3,4)30-17-14(16(24)23(15)17)21-12-22-10-8-6-7-9-11-22/h12-15,17H,5-11H2,1-4H3/b21-12+/t13?,14-,15+,17-/m1/s1
InChI key:InChIKey=XHKFBADIZIDYBU-UCMJJCQDSA-N
SMILES:C(OC(OC(OCC)=O)C)(=O)[C@@H]1N2[C@@]([C@H](N=CN3CCCCCC3)C2=O)(SC1(C)C)[H]
Synonyms:
  • (2S,5R,6R)-6-(((Hexahydro-1H-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Ester with Ethyl 1-Hydroxyethyl Carbonate
  • 1-((Ethoxycarbonyl)oxy)ethyl (2S,5R,6R)-6-(((1E)-Azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(E)-azepan-1-ylmethylene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, [2S-(2α,5α,6β)]-
  • 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(1E)-(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, (2S,5R,6R)-
  • 50846-45-2
  • Kw 1100
  • Bacmecillinam
  • BACMECILLINAM USP/EP/BP
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