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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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan)
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
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