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CAS 64221-86-9

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Imipenem

Description:
Imipenem is a broad-spectrum beta-lactam antibiotic belonging to the carbapenem class, primarily used to treat severe bacterial infections. It is effective against a wide range of Gram-positive and Gram-negative bacteria, including many strains resistant to other antibiotics. Imipenem works by inhibiting bacterial cell wall synthesis, leading to cell lysis and death. It is often administered in combination with cilastatin, a renal dehydropeptidase inhibitor, to prevent its rapid degradation in the kidneys. The compound is typically administered intravenously due to its instability in acidic environments, which limits its oral bioavailability. Imipenem is generally well-tolerated, but potential side effects can include gastrointestinal disturbances, allergic reactions, and, in rare cases, seizures, particularly in patients with renal impairment. Its use is often reserved for serious infections, including those caused by multidrug-resistant organisms, making it a critical agent in the antibiotic arsenal. As with all antibiotics, appropriate use is essential to mitigate the risk of resistance development.
Formula:C12H17N3O4S
InChI:InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
InChI key:InChIKey=ZSKVGTPCRGIANV-ZXFLCMHBSA-N
SMILES:C(O)(=O)C=1N2[C@@]([C@@]([C@@H](C)O)(C2=O)[H])(CC1SCCNC=N)[H]
Synonyms:
  • (5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, [5R-[5α,6α(R*)]]-
  • Imipemide
  • Imipenem
  • Imipenen
  • Mk 0787
  • N-Formimidoylthienamycin
  • Tienamycin
  • 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5R,6S)-
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