Identification
- Summary
Cefditoren is a broad-spectrum third-generation cephalosporin antibiotic typically used to treat bacterial infections of the skin and respiratory tract.
- Brand Names
- Spectracef
- Generic Name
- Cefditoren
- DrugBank Accession Number
- DB01066
- Background
Cefditoren is an oral third-generation cephalosporin. It is commonly marketed under the trade name Spectracef by Cornerstone BioPharma.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cefditoren (DB01066)
- Weight
- Average: 506.578
Monoisotopic: 506.050079786 - Chemical Formula
- C19H18N6O5S3
- Synonyms
- Cefditoren
- Cefditoreno
Pharmacology
- 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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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 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).
- 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.
Target Actions Organism APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - 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%.
- Volume of distribution
- 9.3 ± 1.6 L
- 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.
- Metabolism
Hydrolysis of cefditoren pivoxil to its active component, cefditoren, results in the formation of pivalate. Cefditoren is not appreciably metabolized.
- Route of elimination
Pivalate is mainly eliminated (>99%) through renal excretion, nearly exclusively as pivaloylcarnitine.
- Half-life
Mean terminal elimination half-life is 1.6 ± 0.4 hours in young healthy adults.
- Clearance
- renal cl=4-5 L/h [oral administration]
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefditoren may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefditoren. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefditoren is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefditoren is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefditoren is combined with Acenocoumarol. Acetaminophen Cefditoren may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefditoren. Aclidinium Cefditoren may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefditoren may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Cefditoren. 
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- Avoid multivalent ions. Avoid antacids containing magnesium and aluminum hydroxides when possible, otherwise separate the administration of antacids and this drug by several hours.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefditoren pivoxil 78THA212DH 117467-28-4 AFZFFLVORLEPPO-UVYJNCLZSA-N - International/Other Brands
- Meiact
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefditoren Pivoxil Tablet, film coated 400 mg/1 Oral Pharma Rom Lev Inc. 2010-01-01 Not applicable US 
Cefditoren Pivoxil Tablet, film coated 400 mg/1 Oral Aristos Phamaceuticals, Inc. 2010-01-01 2014-03-31 US Cefditoren Pivoxil Tablet, film coated 200 mg/1 Oral Pharma Rom Lev Inc. 2013-02-12 Not applicable US Cefditoren Pivoxil Tablet, film coated 200 mg/1 Oral Aristos Phamaceuticals, Inc. 2010-01-01 2014-03-31 US Spectracef Tablet, film coated 200 mg/1 Oral Vansen Pharma Inc. 2013-02-05 Not applicable US Spectracef Tablet, film coated 400 mg/1 Oral Cornerstone Therapeutics Inc. 2008-07-21 2014-03-31 US Spectracef Tablet, film coated 400 mg/1 Oral Vansen Pharma Inc. 2013-02-05 Not applicable US Spectracef Tablet, film coated 200 mg/1 Oral Cornerstone Therapeutics Inc. 2008-07-21 2014-03-31 US
Categories
- ATC Codes
- J01DD16 — Cefditoren
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds 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
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 4,5-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines show 10 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / 4,5-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, carboxylic acid (CHEBI:59343)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 81QS09V3YW
- CAS number
- 104145-95-1
- InChI Key
- KMIPKYQIOVAHOP-YLGJWRNMSA-N
- InChI
- 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
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(1Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 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
References
- Synthesis Reference
Kiyoshi Yasui, Masahiro Onodera, Masamichi Sukegawa, Tatsuo Watanabe, Yuichi Yamamoto, Yasushi Murai, Katsuharu Iinuma, "Crystalline substance of cefditoren pivoxyl and the production of the same." U.S. Patent US6294669, issued March, 1986.
US6294669- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015199
- KEGG Drug
- D01628
- PubChem Compound
- 9870843
- PubChem Substance
- 46505471
- ChemSpider
- 8046534
- 83682
- ChEBI
- 59343
- ChEMBL
- CHEMBL1743
- ZINC
- ZINC000004215234
- Therapeutic Targets Database
- DAP000444
- PharmGKB
- PA164747187
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Cefditoren
- FDA label
- Download (200 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia 1 4 Completed Treatment Exacerbation of COPD 1 4 Unknown Status Treatment Rhino Sinusitis 1 3 Completed Treatment Urinary Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Aristos Pharmaceuticals
- Ceph International Corp.
- Cornerstone Pharmacy
- Purdue Pharma LP
- Tedec Meiji Farma S A
- Dosage Forms
Form Route Strength Tablet, film coated Oral 245.1 MG Tablet, film coated Oral Powder Tablet, film coated Oral 400 MG Tablet, film coated Oral 200 MG Tablet 200 mg Tablet 400 mg Granule 100 mg/1sachet Granule Tablet, coated Oral 100 mg Tablet, film coated Oral 100 mg Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 400 mg/1 Tablet - Prices
Unit description Cost Unit Spectracef 28 400 mg tablet Disp Pack 476.99USD disp Spectracef 20 200 mg tablet Disp Pack 340.7USD disp Spectracef 20 400 mg tablet Disp Pack 340.7USD disp Spectracef 200 mg dose pack tablet 16.38USD tablet Spectracef 400 mg dose pack tablet 16.38USD tablet Cefditoren pivoxil 400 mg tablet 14.74USD tablet Spectracef 200 mg tablet 6.26USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5958915 No 1999-09-28 2016-10-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 127-129 °C Not Available water solubility Soluble at levels equal to < 0.1 mg/mL. Not Available - Predicted Properties
Property Value Source Water Solubility 0.0441 mg/mL ALOGPS logP 1.7 ALOGPS logP -0.16 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 2.27 Chemaxon pKa (Strongest Basic) 3.69 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 160.1 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 124.18 m3·mol-1 Chemaxon Polarizability 48.76 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6124 Blood Brain Barrier - 0.9894 Caco-2 permeable - 0.7369 P-glycoprotein substrate Substrate 0.6427 P-glycoprotein inhibitor I Non-inhibitor 0.9042 P-glycoprotein inhibitor II Non-inhibitor 0.7141 Renal organic cation transporter Non-inhibitor 0.8873 CYP450 2C9 substrate Non-substrate 0.8481 CYP450 2D6 substrate Non-substrate 0.8288 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.7687 CYP450 2C9 inhibitor Non-inhibitor 0.7816 CYP450 2D6 inhibitor Non-inhibitor 0.892 CYP450 2C19 inhibitor Non-inhibitor 0.7665 CYP450 3A4 inhibitor Non-inhibitor 0.7867 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9431 Ames test Non AMES toxic 0.7987 Carcinogenicity Non-carcinogens 0.8588 Biodegradation Not ready biodegradable 0.984 Rat acute toxicity 1.8714 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9939 hERG inhibition (predictor II) Non-inhibitor 0.8831
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Yamada M, Watanabe T, Miyara T, Baba N, Saito J, Takeuchi Y, Ohsawa F: Crystal structure of cefditoren complexed with Streptococcus pneumoniae penicillin-binding protein 2X: structural basis for its high antimicrobial activity. Antimicrob Agents Chemother. 2007 Nov;51(11):3902-7. Epub 2007 Aug 27. [Article]
- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Martin SI, Kaye KM: Beta-lactam antibiotics: newer formulations and newer agents. Infect Dis Clin North Am. 2004 Sep;18(3):603-19, ix. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:21