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CAS 32886-97-8

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Pivmecillinam

Description:
Pivmecillinam is a semi-synthetic antibiotic belonging to the penicillin class, primarily used to treat urinary tract infections caused by susceptible bacteria. Its chemical structure is characterized by the presence of a beta-lactam ring, which is essential for its antibacterial activity. Pivmecillinam is a prodrug of mecillinam, meaning it is converted into its active form in the body. It exhibits a broad spectrum of activity against Gram-negative bacteria, particularly Enterobacteriaceae, and is effective against certain Gram-positive organisms as well. The substance is generally well-tolerated, with common side effects including gastrointestinal disturbances and allergic reactions in sensitive individuals. Pivmecillinam is typically administered orally and is known for its favorable pharmacokinetic properties, including good tissue penetration and a relatively long half-life. Its use is particularly significant in regions where antibiotic resistance is a concern, as it provides an alternative treatment option for uncomplicated urinary tract infections. As with all antibiotics, appropriate use is crucial to minimize the development of resistance.
Formula:C21H33N3O5S
InChI:InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChI key:InChIKey=NPGNOVNWUSPMDP-HLLBOEOZSA-N
SMILES:C(OCOC(C(C)(C)C)=O)(=O)[C@@H]1N2[C@@]([C@H](N=CN3CCCCCC3)C2=O)(SC1(C)C)[H]
Synonyms:
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl 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-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [2S-(2α,5α,6β)]-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, hydroxymethyl ester pivalate (ester), (+)-
  • Amdinocillin pivoxil
  • Fl 1039
  • Pivamdinocillin
  • Pivmecilinamo
  • [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • Pivmecillinam
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