Cefamandole

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:	1974
Development status:	Approved, off-patent, discontinued in many countries

Chemical structure(s):
Canonical SMILES:	CN1C(=NN=N1)SCC2=C(C(=O)O)N3C(=O)[C@H]([C@H]3SC2)NC(=O)[C@@H](C4=CC=CC=C4)O
Isomeric SMILES:	CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
InChI:	InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChI Key:	OLVCFLKTBJRLHI-AXAPSJFSSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/456255

External links:
Guide to Pharmacology:	cefamandole
Main Source:	https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=11047