Compound ID | 1890

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Cefamandole

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP); PBP inhibitor
Target Pathogen: Active against Gram-positive bacteria and against many Enterobacteriaceae but vulnerable to extended-spectrum beta-lactamases (ESBL)
Description: Semisynthetic Cephalosporin, derived from Cephalosporin C
Year first mentioned: 1974
Highest development stage: Approved
Development status: Approved
Reason dropped: Discontinued/Withdrawn in US
Chemical structure(s):
Click here for structure editor
Molecular weight: 462.51
Iso. 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 Key: OLVCFLKTBJRLHI-AXAPSJFSSA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/456255
Guide to Pharmacology: cefamandole
Citation: https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=11047

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