Compound ID | 439

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TOC-39

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: 561.62
Iso. SMILES: C1C(=C(N2C(S1)C(C2=O)NC(=O)/C(=N\O)/C3=CSC(=N3)N)C(=O)[O-])/C=C/SC4=CC=[N+](C=C4)CC(=O)N
InChI Key: GDJQCYDEHYQKSL-ZZXKWVIFSA-N
Can. SMILES: C1=C(C=C[N+](=C1)CC(=O)N)S/C=C/C2=C(C(=O)[O-])N3C(=O)C(C3SC2)NC(=O)/C(=N\O)/C4=CSC(=N4)N
InChI: InChI=1S/C21H19N7O6S3/c22-13(29)7-27-4-1-11(2-5-27)35-6-3-10-8-36-19-15(18(31)28(19)16(10)20(32)33)25-17(30)14(26-34)12-9-37-21(23)24-12/h1-6,9,15,19H,7-8H2,(H6-,22,23,24,25,29,30,32,33,34)/b6-3+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10415421
Citation: https://doi.org/10.1128/aac.39.5.1120

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