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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]