cefcapene   Click here for help

GtoPdb Ligand ID: 12053

Synonyms: Flomox® (cefcapene pivoxil) | S-1006
Approved drug
cefcapene is an approved drug (Japan)
Compound class: Synthetic organic
Comment: Cefcapene is a third generation cephalosporin, belonging to the β-lactam class of antibacterial compounds. The compound was developed by Shionogi Research Laboratories (Osaka, Japan) and has broad-spectrum activity against both Gram-positive and Gram-negative bacteria [1]. It is formulated as an ester-type prodrug (cefcapene pivoxil, PubChem CID 5282438) to provide acceptable bioavailability for oral use.
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 4
Rotatable bonds 9
Topological polar surface area 231.48
Molecular weight 453.08
XLogP -2.62
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 CC/C=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N
Isomeric SMILES CC/C=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O
InChI InChI=1S/C17H19N5O6S2/c1-2-3-8(9-6-30-16(18)20-9)12(23)21-10-13(24)22-11(15(25)26)7(4-28-17(19)27)5-29-14(10)22/h3,6,10,14H,2,4-5H2,1H3,(H2,18,20)(H2,19,27)(H,21,23)(H,25,26)/b8-3-/t10-,14-/m1/s1
InChI Key HJJRIJDTIPFROI-NVKITGPLSA-N
No information available.
Summary of Clinical Use Click here for help
Cefcapene pivoxil has marketing authorisation in Japan (granted in 1997). There is no information regarding approval for clinical use of this drug on the US FDA or European Medicines Agency websites.