cefsulodin   Click here for help

GtoPdb Ligand ID: 10783

Synonyms: Cefonomil® | CGP-7174-E | CGP7174/E
Compound class: Synthetic organic
Comment: Cefsulodin is a semi-synthetic, third-generation cephalosporin antibacterial. It is active against Pseudomonas aeruginosa and Staphylococcus aureus, but little activity against other bacteria [4-5].
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 224.56
Molecular weight 532.07
XLogP 0.74
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C([C@H](S(=O)(=O)O)c1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccc(cc1)C(=O)N
Isomeric SMILES O=C([C@H](S(=O)(=O)O)c1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccc(cc1)C(=O)N
InChI InChI=1S/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17-,21-/m1/s1
InChI Key SYLKGLMBLAAGSC-QLVMHMETSA-N
References
1. Brouard R, Tozer TN, Merdjan H, Guillemin A, Baumelou A. (1988)
Transperitoneal movement and pharmacokinetics of cefotiam and cefsulodin in patients on continuous ambulatory peritoneal dialysis.
Clin Nephrol, 30 (4): 197-206. [PMID:3214965]
2. Elder HA, Roy I. (1984)
Treatment of urinary tract infections due to Pseudomonas aeruginosa with cefsulodin.
Rev Infect Dis, 6 Suppl 3: S734-43. [PMID:6443774]
3. Lecaillon JB, Rouan MC, Binswanger U, Guibert J, Schoeller JP. (1984)
Pharmacokinetics of cefotiam and cefsulodin after simultaneous administration to patients with impaired renal function.
Antimicrob Agents Chemother, 26 (3): 368-72. [PMID:6095754]
4. Neu HC, Scully BE. (1984)
Activity of cefsulodin and other agents against Pseudomonas aeruginosa.
Rev Infect Dis, 6 Suppl 3: S667-77. [PMID:6443768]
5. Wright DB. (1986)
Cefsulodin.
Drug Intell Clin Pharm, 20 (11): 845-9. [PMID:3536385]