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):
Canonical SMILES:	CO[C@]1(C(=O)N2C(=C(COC(=O)N)CS[C@H]12)C(=O)O)NC(=O)CC3=CC=CS3
Isomeric SMILES:	CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)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
InChI Key:	WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/441199

External links:
Guide to Pharmacology:	cefoxitin
Main Source:	https://link.springer.com/article/10.1007/s10096-019-03701-0