cefclidin   Click here for help

GtoPdb Ligand ID: 10771

Synonyms: cefclidine | E-1040 | E1040
Compound class: Synthetic organic
Comment: Cefclidin (E1040) is a fourth-generation cephalosporin antibacterial that disrupts cell wall formation [2-3]. It exhibits strong antibacterial activity against glucose non-fermentative bacillus bacteria, but is ineffective against gram-positive cocci.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 259.56
Molecular weight 550.14
XLogP -4.91
No. Lipinski's rules broken 1
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Canonical SMILES CO/N=C(/c1nsc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]12CCC(CC1)(CC2)C(=O)N
Isomeric SMILES CO/N=C(/c1nsc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]12CCC(CC1)(CC2)C(=O)N
InChI InChI=1S/C21H26N8O6S2/c1-35-26-11(14-25-20(23)37-27-14)15(30)24-12-16(31)28-13(18(32)33)10(9-36-17(12)28)8-29-5-2-21(3-6-29,4-7-29)19(22)34/h12,17H,2-9H2,1H3,(H5-,22,23,24,25,27,30,32,33,34)/b26-11-/t12-,17-,21?,29?/m1/s1
1. Nakashima M, Uematsu T, Kanamara M, Ueno K, Setoyama T, Tomono Y, Ohno T, Okano K, Morishita N. (1989)
Phase I study of E1040, a new parenteral cephem antibiotic.
J Clin Pharmacol, 29 (2): 144-50. [PMID:2715371]
2. Sugiyama I, Komatsu Y, Yamauchi H. (1992)
Synthesis and structure-activity relationships of a new series of cephalosporins, E1040 and related compounds.
J Antibiot, 45 (1): 103-12. [PMID:1548180]
3. Watanabe N, Katsu K, Moriyama M, Kitoh K. (1988)
In vitro evaluation of E1040, a new cephalosporin with potent antipseudomonal activity.
Antimicrob Agents Chemother, 32 (5): 693-701. [PMID:3134847]