Cefotaxime

Class: Beta-lactam (cephalosporin, third 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 Cephalosporine, derived from Cephalosporin C
Year first mentioned:	1979
Development status:	Approved, off-patent

Chemical structure(s):
Canonical SMILES:	CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OC)/C3=CSC(=N3)N
Isomeric SMILES:	CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)O
InChI:	InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChI Key:	GPRBEKHLDVQUJE-QSWIMTSFSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5742673

External links:
Guide to Pharmacology:	cefotaxime
Main Source:	https://pubmed.ncbi.nlm.nih.gov/2083516/
Citations:	https://pubmed.ncbi.nlm.nih.gov/31538190/ https://pubmed.ncbi.nlm.nih.gov/31697336/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8748331/