Cefditoren
Grundinformationen
- CAS
104145-95-1- Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(/C=C\c3scnc3C)CS[C@H]12)c1csc(N)n1- InChIKey
KMIPKYQIOVAHOP-YLGJWRNMSA-N- Summenformel
- C19H18N6O5S3
- Durchschnittliche Molmasse
- 506,6 g/mol
- Monoisotopische Masse
- 506,05008122
Überblick
Cefditoren is a broad spectrum, third-generation cephalosporin antibiotic with (Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. Generally administered as its orally absorbed pivaloyloxymethyl ester prodrug, it is used for the treatment of mild to moderate infections caused by susceptible strains of microorganisms in acute bacterial exacerbation of chronic bronchitis, community-acquired pneumonia, pharyngitis/tonsillitis, and uncomplicated skin and skin-structure infections. It has a role as an antibacterial drug. It is a cephalosporin and a carboxylic acid.
Namen und Bezeichner
- Bevorzugter Name
- Cefditoren
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-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
- Englischer Name
- Cefditoren
- Summenformel
- C19H18N6O5S3
- Molmasse
- 506.58
Namen und Synonyme
Cefditoren104145-95-1cefditoreneCefditoreno81QS09V3YWCHEBI:593435-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (6R-(3(Z),6alpha,7beta(Z)))-cefditorenum(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(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 acidRefChem:56293J01DD16
Weitere Namen anzeigen
CefotoloneCeftopolamCefditoren AcidCefditoren-13C-D313C,2H3]-CefditorenCefditoren USP/EP/BPCefditoren Pivoxil Impurity 22 Monomer(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 242 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 12
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 928
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Solubility
Soluble at levels equal to < 0.1 mg/mL.
4.41e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Melting Point
127-129 °C
127 - 129 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Dichte
- 1.75 · 1.75
- pka
- 2.43 · 2.43±0.50(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Light yellow to yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefditoren
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingBinding of cefditoren to plasma proteins averages 88% from <i>in vitro</i> determinations, and is concentration-independent at cefditoren concentrations ranging from 0.05 to 10 mg/mL.
Pharmacodynamics
Cefditoren pivoxil is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cefditoren. Cefditoren is a cephalosporin with antibacterial activity against gram-positive and gram-negative pathogens. Cefditoren is effective against <i>Staphylococcus aureus</i> (methicillin-susceptible strains, including b-lactamase-producing strains), penicillin-susceptible strains of <i>Staphylococcus aureus</i> and <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>, <i>Haemophilus influenzae</i> (including b-lactamase-producing strains), <i>Haemophilus parainfluenzae</i> (including b-lactamase-producing strains), <i>Moraxella catarrhalis</i> (including b-lactamase-producing strains), <i>Streptococcus agalactiae</i>, <i>Streptococcus</i> Groups C and G, and <i>Streptococcus</i>, viridans group (penicillin-susceptible and -intermediate strains).
Mechanism of Action
The bactericidal activity of cefditoren results 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.
Biological Half-LifeMean terminal elimination half-life is 1.6 ± 0.4 hours in young healthy adults.
Metabolism/MetabolitesHydrolysis of cefditoren pivoxil to its active component, cefditoren, results in the formation of pivalate. Cefditoren is not appreciably metabolized.
FDA Pharmacological Classification
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