Compound ID | 440

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TOC-50

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Able to outcompete penicillin G in binding to PBP of methicillin-resistant Staphylococcus aureus
Target Pathogen: Active against methicillin-resistant and -susceptible Staphylococcus aureus
Description: Parenteral cephalosporin; Hanaki H, Akagi H, Shimizu C, et al., Active new Cephalosporin, TOC-39, TOC-50, against multi-resistant MRSA. 33rd-Intersci-Conf-Antimicrobial-Agents-Chemother 1993; 282.
Institute where first reported: Taiho Pharmaceuticals, Japan and Otsuka Chemical Co., Japan
Year first mentioned: 1993
Development status: Experimental
Chemical structure(s):
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Molecular weight:
Iso. SMILES: C[N+]1=CC=C(SC=CC2=C(N3[C@H](SC2)C(NC(=O)C(=NO)C4=CSC(N)=N4)C3=O)C(=O)O)C=C1
InChI Key: YOPKORGDBWAKSB-XPKAQORNSA-O
Can. SMILES: C[N+]1=CC=C(C=C1)SC=CC2=C(C(=O)O)N3C(=O)C([C@H]3SC2)NC(=O)C(=NO)C4=CSC(=N4)N
InChI: InChI=1S/C20H18N6O5S3/c1-25-5-2-11(3-6-25)32-7-4-10-8-33-18-14(17(28)26(18)15(10)19(29)30)23-16(27)13(24-31)12-9-34-20(21)22-12/h2-7,9,14,18H,8H2,1H3,(H4-,21,22,23,27,29,30,31)/p+1/t14?,18-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/substance/274913048
Citation: https://doi.org/10.1159/000239527

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