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CAS 50972-17-3

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Bacampicillin

Description:
Bacampicillin is a semi-synthetic antibiotic belonging to the penicillin class, specifically designed to enhance the stability of the penicillin structure against gastric acid, thereby improving its oral bioavailability. It is characterized by its broad-spectrum activity against various Gram-positive and some Gram-negative bacteria, making it effective in treating a range of infections. Bacampicillin is a prodrug that is converted into ampicillin in the body, which is the active form responsible for its antibacterial effects. The compound typically exhibits good absorption when administered orally and is often used in the treatment of respiratory tract infections, urinary tract infections, and skin infections. Its mechanism of action involves inhibiting bacterial cell wall synthesis, leading to cell lysis and death. Bacampicillin is generally well-tolerated, but like other antibiotics, it may cause side effects such as gastrointestinal disturbances or allergic reactions in some individuals. As with any antibiotic, appropriate use is crucial to prevent the development of antibiotic resistance.
Formula:C21H27N3O7S
InChI:InChI=1/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI key:InChIKey=PFOLLRNADZZWEX-FFGRCDKISA-N
SMILES:C(OC(OC(OCC)=O)C)(=O)[C@@H]1N2[C@@]([C@H](NC([C@H](N)C3=CC=CC=C3)=O)C2=O)(SC1(C)C)[H]
Synonyms:
  • (2S,5R,6R)-6((R)-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ester with ethyl 1-hydroxyethylcarbonate
  • 1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanate
  • 1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6((R)-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat
  • 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]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-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl ester, (2S-(2alpha,5alpha,6beta(S*)))-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, [2S-[2α,5α,6β(S*)]]-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]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-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, (2S,5R,6R)-
  • 6-((R)-2-Amino-2-phenylacetamido)penicillansaeure-(1-(ethoxycarbonyloxy)ethylester
  • See more synonyms
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