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Cefditoren

Catalog No. DB01066 Name DrugBank
CAS Number 117467-28-4 Website http://www.ualberta.ca/
M. F. C25H28N6O7S3 Telephone (780) 492-3111
M. W. 620.72082 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 937

SYNONYMS

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-carbonyloxy]methyl 2,2-dimethylpropanoate
IUPAC Traditional 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-carbonyloxy]methyl 2,2-dimethylpropanoate
Brand Name
Spectracef
Meiact
Synonyms
Cefditoren Pivoxil
CDTR-PI
Cefditoren Pivaloyloxymethyl Ester

DATABASE IDS

CAS Number 117467-28-4

PROPERTIES

Solubility Soluble at levels equal to < 0.1 mg/mL.

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Cefditoren is a third-generation cephalosporin antibiotic for oral use. It is commonly marketed under the trade name Spectracef by Cornerstone BioPharma.
Indication For the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are 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.
Pharmacology 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 Staphylococcus aureus (methicillin-susceptible strains, including b-lactamase-producing strains), penicillin-susceptible strains of Staphylococcus aureus and Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae (including b-lactamase-producing strains), Haemophilus parainfluenzae (including b-lactamase-producing strains), Moraxella catarrhalis (including b-lactamase-producing strains), Streptococcus agalactiae, Streptococcus Groups C and G, and Streptococcus, viridans group (penicillin-susceptible and -intermediate strains).
Toxicity Information on cefditoren pivoxil overdosage in humans is not available. However, with other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions. In acute animal toxicity studies, cefditoren pivoxil when tested at the limit oral doses of 5100 mg/kg in rats and up to 2000 mg/kg in dogs did not exhibit any health effects of concern.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hydrolysis of cefditoren pivoxil to its active component, cefditoren, results in the formation of pivalate. Cefditoren is not appreciably metabolized.
Absorption Following oral administration, cefditoren pivoxil is absorbed from the gastrointestinal tract and hydrolyzed to cefditoren by esterases. Under fasting conditions, the estimated absolute bioavailability of cefditoren pivoxil is approximately 14%. The absolute bioavailability of cefditoren pivoxil administered with a low fat meal (693 cal, 14 g fat, 122 g carb, 23 g protein) is 16.1 ± 3.0%.
Half Life Mean terminal elimination half-life is 1.6 ± 0.4 hours in young healthy adults.
Protein Binding Binding of cefditoren to plasma proteins averages 88% from in vitro determinations, and is concentration-independent at cefditoren concentrations ranging from 0.05 to 10 mg/mL.
Elimination Pivalate is mainly eliminated (>99%) through renal excretion, nearly exclusively as pivaloylcarnitine.
Distribution * 9.3 ± 1.6 L
Clearance * renal cl=4-5 L/h [oral administration]
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]
External Links
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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