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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Japan PMDA (0)
IUPAC Name Click here for help
(6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7006 cefcapene
Synonyms Click here for help
Flomox® (cefcapene pivoxil) | S-1006
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefcapene
Other databases
CAS Registry No. 135889-00-8 (source: Scifinder)
ChEBI CHEBI:131729
ChEMBL Ligand CHEMBL582912
DrugBank Ligand DB13461
DrugCentral Ligand 4159
GtoPdb PubChem SID 472319175
PubChem CID 6436055
Search Google for chemical match using the InChIKey HJJRIJDTIPFROI-NVKITGPLSA-N
Search Google for chemicals with the same backbone HJJRIJDTIPFROI
Search PubMed clinical trials cefcapene
Search PubMed titles cefcapene
Search PubMed titles/abstracts cefcapene
UniChem Compound Search for chemical match using the InChIKey HJJRIJDTIPFROI-NVKITGPLSA-N
UniChem Connectivity Search for chemical match using the InChIKey HJJRIJDTIPFROI-NVKITGPLSA-N