Compound ID | 1878

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Cefazolin

Class: Beta-lactam (cephalosporin, first 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 moderately against Enterobacteriaceae but high resistance rates in Enterobacteriaceae
Description: Semisynthetic Cephalosporin, derived from Cephalosporin C
Year first mentioned: 1967
Highest developmental phase: Approved by FDA in 1987
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 454.51
Iso. SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
InChI Key: MLYYVTUWGNIJIB-BXKDBHETSA-N
Can. SMILES: CC1=NN=C(SCC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)CN4C=NN=N4)S1
InChI: InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/33255
Guide to Pharmacology: cefazolin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8960241/
  • https://www.nhs.uk/medicines/cefalexin/
  • https://pubmed.ncbi.nlm.nih.gov/1105179/

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