Compound ID | 1900

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Cefbuperazone

Synonym(s): T-1982

Class: Beta-lactam (cephalosporin, second generation)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria and against many Enterobacteriaceae but vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporin, derived from Cephalosporin C
Year first mentioned: 1982
Development status: Approved, off-patent, discontinued in many countries
Chemical structure(s):
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Molecular weight: 627.65
Iso. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]2([C@@H]3N(C2=O)C(=C(CS3)CSC4=NN=NN4C)C(=O)O)OC
InChI Key: SMSRCGPDNDCXFR-CYWZMYCQSA-N
Can. SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@@]2(C(=O)N3C(=C(CS[C@H]23)CSC4=NN=NN4C)C(=O)O)OC
InChI: InChI=1S/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/127527
Guide to Pharmacology: cefbuperazone
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/27394175/
  • https://pubmed.ncbi.nlm.nih.gov/3879464/

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