| Common Name |
Cefditoren
| Description |
Cefditoren is only found in individuals that have used or taken this drug. It is a third-generation cephalosporin antibiotic for oral use. It is commonly marketed under the trade name Spectracef by Cornerstone BioPharma.The bactericidal activity of cefditoren reslits from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefditoren is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
CDTR-PIHMDB
Cefditoren pivaloyloxymethyl esterHMDB
Cefditoren pivoxilHMDB
Cefditoren, sodium salt, (6R-(3(Z),6alpha,7beta(Z)))-isomerMeSH
| Chemical Formlia |
C19H18N6O5S3
| Average Molecliar Weight |
506.578
| Monoisotopic Molecliar Weight |
506.050079786
| IUPAC Name |
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| Traditional Name |
cefditoren
| CAS Registry Number |
117467-28-4
| SMILES |
[H][C@]12SCC(C=C/C3=C(C)N=CS3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)C1=CSC(N)=N1)C(O)=O
| InChI Identifier |
InChI=1S/C19H18N6O5S3/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29)/b4-3-,24-12-/t13-,17-/m1/s1
| InChI Key |
KMIPKYQIOVAHOP-YLGJWRNMSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Lactams
| Direct Parent |
Cephalosporins
| Alternative Parents |
N-acyl-alpha amino acids and derivatives
2,4-disubstituted thiazoles
4,5-disubstituted thiazoles
1,3-thiazines
Primary aromatic amines
2-amino-1,3-thiazoles
Tertiary carboxylic acid amides
Heteroaromatic compounds
Secondary carboxylic acid amides
Amino acids
Azetidines
Thiohemiaminal derivatives
Monocarboxylic acids and derivatives
Azacyclic compounds
Dialkylthioethers
Carboxylic acids
Organic oxides
Organopnictogen compounds
Carbonyl compounds
Hydrocarbon derivatives
| Substituents |
Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
2,4-disubstituted 1,3-thiazole
4,5-disubstituted 1,3-thiazole
Meta-thiazine
Primary aromatic amine
1,3-thiazol-2-amine
Tertiary carboxylic acid amide
Thiazole
Heteroaromatic compound
Azole
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Azetidine
Azacycle
Dialkylthioether
Hemithioaminal
Carboxylic acid derivative
Carboxylic acid
Thioether
Monocarboxylic acid or derivatives
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Amine
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
cephalosporin (CHEBI:59343 )
carboxylic acid (CHEBI:59343 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Bacterial Agents
Cephalosporins
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point127 – 129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.41e-02 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.044 mg/mLALOGPS
logP1.7ALOGPS
logP-0.15ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)4.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area160.1 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.18 m3·mol-1ChemAxon
Polarizability49.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01066
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01066
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01066
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
8046534
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Cefditoren
| NuGOwiki Link |
HMDB15199
| Metagene Link |
HMDB15199
| METLIN ID |
Not Available
| PubChem Compound |
9870843
| PDB ID |
Not Available
| ChEBI ID |
59343
Product: GW311617
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Tempera G, Furneri PM, Carlone NA, Cocuzza C, Rigoli R, Musumeci R, Pilloni AP, Prenna M, Tufano MA, Tullio V, Vitali LA, Nicoletti G: Antibiotic susceptibility of respiratory pathogens recently isolated in Italy: focus on cefditoren. J Chemother. 2010 Jun;22(3):153-9. [PubMed:20566418 ]
|
PMID: 16302793
