Compound ID | 1895

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Cefoxitin

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 and some anaerobes; it is less vulnerable to extended-spectum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporin (cephamycin), derived from Cephalosporin C
Year first mentioned: 1972
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 427.45
Iso. SMILES: CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
InChI Key: WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Can. SMILES: CO[C@]1(C(=O)N2C(=C(COC(=O)N)CS[C@H]12)C(=O)O)NC(=O)CC3=CC=CS3
InChI: InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/441199
Guide to Pharmacology: cefoxitin
Citation: https://link.springer.com/article/10.1007/s10096-019-03701-0

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