Cefditoren

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1A
inhibitor
Clostridium 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
Adverseeffects
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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.

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.
DrugInteraction
AbacavirCefditoren may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefditoren.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefditoren is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefditoren is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefditoren is combined with Acenocoumarol.
AcetaminophenCefditoren may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefditoren.
AclidiniumCefditoren may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCefditoren may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Cefditoren.
Interactions
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Food Interactions
  • 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

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Product Ingredients
IngredientUNIICASInChI Key
Cefditoren pivoxil78THA212DH117467-28-4AFZFFLVORLEPPO-UVYJNCLZSA-N
International/Other Brands
Meiact
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cefditoren PivoxilTablet, film coated400 mg/1OralPharma Rom Lev Inc.2010-01-01Not applicableUS flag
Cefditoren PivoxilTablet, film coated400 mg/1OralAristos Phamaceuticals, Inc.2010-01-012014-03-31US flag
Cefditoren PivoxilTablet, film coated200 mg/1OralPharma Rom Lev Inc.2013-02-12Not applicableUS flag
Cefditoren PivoxilTablet, film coated200 mg/1OralAristos Phamaceuticals, Inc.2010-01-012014-03-31US flag
SpectracefTablet, film coated200 mg/1OralCornerstone Therapeutics Inc.2008-07-212014-03-31US flag
SpectracefTablet, film coated200 mg/1OralVansen Pharma Inc.2013-02-05Not applicableUS flag
SpectracefTablet, film coated400 mg/1OralCornerstone Therapeutics Inc.2008-07-212014-03-31US flag
SpectracefTablet, film coated400 mg/1OralVansen Pharma Inc.2013-02-05Not applicableUS flag

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-[(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
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
  1. 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]
Human Metabolome Database
HMDB0015199
KEGG Drug
D01628
PubChem Compound
9870843
PubChem Substance
46505471
ChemSpider
8046534
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Obstructive Airways Disease Exacerbated1
4RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia1
4Unknown StatusTreatmentRhino Sinusitis1
3CompletedTreatmentUrinary Tract Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Aristos Pharmaceuticals
  • Ceph International Corp.
  • Cornerstone Pharmacy
  • Purdue Pharma LP
  • Tedec Meiji Farma S A
Dosage Forms
FormRouteStrength
Powder
Tablet, film coatedOral200 MG
Tablet, film coatedOral400 MG
Tablet, film coatedOral
Tablet200 mg
Tablet400 mg
Granule100 mg/1sachet
Granule
Tablet, coatedOral100 mg
Tablet, film coatedOral100 mg
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral400 mg/1
Tablet
Prices
Unit descriptionCostUnit
Spectracef 28 400 mg tablet Disp Pack476.99USD disp
Spectracef 20 200 mg tablet Disp Pack340.7USD disp
Spectracef 20 400 mg tablet Disp Pack340.7USD disp
Spectracef 200 mg dose pack tablet16.38USD tablet
Spectracef 400 mg dose pack tablet16.38USD tablet
Cefditoren pivoxil 400 mg tablet14.74USD tablet
Spectracef 200 mg tablet6.26USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5958915No1999-09-282016-10-14US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)127-129 °CNot Available
water solubilitySoluble at levels equal to < 0.1 mg/mL.Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0441 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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6124
Blood Brain Barrier-0.9894
Caco-2 permeable-0.7369
P-glycoprotein substrateSubstrate0.6427
P-glycoprotein inhibitor INon-inhibitor0.9042
P-glycoprotein inhibitor IINon-inhibitor0.7141
Renal organic cation transporterNon-inhibitor0.8873
CYP450 2C9 substrateNon-substrate0.8481
CYP450 2D6 substrateNon-substrate0.8288
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7687
CYP450 2C9 inhibitorNon-inhibitor0.7816
CYP450 2D6 inhibitorNon-inhibitor0.892
CYP450 2C19 inhibitorNon-inhibitor0.7665
CYP450 3A4 inhibitorNon-inhibitor0.7867
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9431
Ames testNon AMES toxic0.7987
CarcinogenicityNon-carcinogens0.8588
BiodegradationNot ready biodegradable0.984
Rat acute toxicity1.8714 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.8831
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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 on June 13, 2005 13:24 / Updated on May 07, 2021 21:21