Ceftaroline fosamil is an antibacterial agent used to treat various bacterial infections, such as acute bacterial skin and skin structure infections and community-acquired bacterial pneumonia.
- Brand Names
- Teflaro, Zinforo
- Generic Name
- Ceftaroline fosamil
- DrugBank Accession Number
Ceftaroline fosamil is a cephalosporin antibacterial indicated for the treatment of the following infections caused by designated susceptible bacteria: Acute bacterial skin and skin structure infections. Community-acquired bacterial pneumonia.
- Small Molecule
- Approved, Investigational
- Average: 684.67
- Chemical Formula
- Ceftarolina fosamilo
- Ceftaroline fosamil
- Ceftarolinum fosamilum
- External IDs
- PPI 0903
Ceftaroline fosamil is indicated for the treatment of patients with the following infections caused by susceptible isolates of the designated microorganisms.Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset
- Associated Conditions
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
The time that unbound plasma concentration of ceftaroline exceeds the minimum inhibitory concentration (MIC) of the infecting organism has been shown to best correlate with efficacy in a neutropenic murine thigh infection model with S. aureus and S. pneumoniae.
No significant effect on QTc (corrected QT interval) interval was detected at peak plasma concentration or at any other time.
- Mechanism of action
Ceftaroline fosamil is an antibacterial drug.
- Volume of distribution
Median 20.3 L (18.3-21.6 L).
- Protein binding
Ceftaroline fosamil is converted into bioactive ceftaroline in plasma by a phosphatase enzyme. Hydrolysis of the beta-lactam ring of ceftaroline occurs to form the microbiologically inactive, open-ring metabolite ceftaroline M-1.
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- Route of elimination
primarily eliminated by the kidneys (6% in feces within 48 hours).
1.60 hours (600 mg dose).
- Adverse Effects
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LD50/LC50: Draize test, rabbit, eye: 100 mg/24H Moderate; Oral, mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- 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 Abacavir Ceftaroline fosamil 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 Ceftaroline fosamil. Aceclofenac The risk or severity of nephrotoxicity can be increased when Ceftaroline fosamil is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Ceftaroline fosamil is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Ceftaroline fosamil is combined with Acenocoumarol. Acetaminophen Ceftaroline fosamil 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 Ceftaroline fosamil. Aclidinium Ceftaroline fosamil may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Ceftaroline fosamil 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 Ceftaroline fosamil is combined with Acyclovir.Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more
- Food Interactions
- No interactions found.
- Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets
- Product Ingredients
Ingredient UNII CAS InChI Key Ceftaroline fosamil acetate EZ9W6O5S09 400827-46-5 UGHHNQFYEVOFIV-VRDMTWHKSA-N Ceftaroline fosamil acetate monohydrate P9VXV1408Y 400827-55-6 KRWPPVCZNGQQHZ-IINIBMQSSA-N
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Teflaro Powder, for solution 600 mg/20mL Intravenous Allergan, Inc. 2010-10-29 Not applicable Teflaro Powder, for solution 400 mg/20mL Intravenous Allergan, Inc. 2010-10-29 Not applicable Zinforo Injection, powder, for solution 600 mg Intravenous Pfizer Ireland Pharmaceuticals 2016-09-08 Not applicable
- ATC Codes
- J01DI02 — Ceftaroline fosamil
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Sub Class
- Beta lactams
- Direct Parent
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Aryl thioethers / 2,4-disubstituted thiazoles / N-methylpyridinium compounds / Vinylogous thioesters / 1,3-thiazines / Pyridinium derivatives / Organic phosphoramides / Thiadiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Thioenol ethers / Secondary carboxylic acid amides / Azetidines / Carboxylic acid salts / Thiohemiaminal derivatives / Sulfenyl compounds / Azacyclic compounds / Carboxylic acids / Dialkylthioethers / Monocarboxylic acids and derivatives / Organic zwitterions / Organopnictogen compounds / Organonitrogen compounds / Organic salts / Hydrocarbon derivatives / Carbonyl compounds / Organic oxides show 18 more
- 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid salt / Cephalosporin / Dialkylthioether / Hemithioaminal / Heteroaromatic compound / Hydrocarbon derivative / Meta-thiazine / Monocarboxylic acid or derivatives / N-acyl-alpha amino acid or derivatives / N-methylpyridinium / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic phosphoric acid amide / Organic phosphoric acid derivative / Organic salt / Organic zwitterion / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Pyridine / Pyridinium / Secondary carboxylic acid amide / Sulfenyl compound / Tertiary carboxylic acid amide / Thiadiazole / Thiazole / Thioenolether / Thioether / Vinylogous thioester show 32 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, iminium betaine, 1,3-thiazole, oxime O-ether, thiadiazoles, organic phosphoramidate (CHEBI:70718)
- Affected organisms
- Gram-negative Bacteria
- Gram-positive Bacteria
- Streptococcus pneumoniae
- Staphylococcus aureus
- CAS number
- InChI Key
- IUPAC Name
- Synthesis Reference
- General References
- Steed ME, Rybak MJ: Ceftaroline: a new cephalosporin with activity against resistant gram-positive pathogens. Pharmacotherapy. 2010 Apr;30(4):375-89. doi: 10.1592/phco.30.4.375. [Article]
- Kollef MH: New antimicrobial agents for methicillin-resistant Staphylococcus aureus. Crit Care Resusc. 2009 Dec;11(4):282-6. [Article]
- Kanafani ZA, Corey GR: Ceftaroline: a cephalosporin with expanded Gram-positive activity. Future Microbiol. 2009 Feb;4(1):25-33. doi: 10.2217/174609126.96.36.199. [Article]
- Parish D, Scheinfeld N: Ceftaroline fosamil, a cephalosporin derivative for the potential treatment of MRSA infection. Curr Opin Investig Drugs. 2008 Feb;9(2):201-9. [Article]
- MacGowan AP, Noel AR, Tomaselli S, Bowker KE: Pharmacodynamics of ceftaroline against Staphylococcus aureus studied in an in vitro pharmacokinetic model of infection. Antimicrob Agents Chemother. 2013 Jun;57(6):2451-6. doi: 10.1128/AAC.01386-12. Epub 2013 Mar 4. [Article]
- FDA label
- Download (210 KB)
- Download (568 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Cystic Fibrosis (CF) 1 4 Completed Not Available Infection 1 4 Completed Treatment Bacteremia 1 4 Completed Treatment Bacterial Pneumonia / Community-acquired 1 4 Completed Treatment Infection 1 4 Completed Treatment Infection / Pneumonia 1 4 Completed Treatment Methicillin-resistant Staphylococcus Aureus (MRSA) Bacteremia / Staphylococcus Aureus Bacteraemia 1 4 Completed Treatment Skin Diseases, Infectious / Staphylococcal Skin Infections 1 4 Recruiting Treatment Community-acquired Pneumonia, Influenza, COVID-19 / Coronavirus Disease 2019 (COVID‑19) 1 4 Terminated Prevention Acute Bacterial Skin and Skin Structure Infection (ABSSSI) / Bacteremia / Endocarditis / Healthcare Associated Pneumonia / Osteomyelitis/Septic Arthritis 1
- Not Available
- Not Available
- Dosage Forms
Form Route Strength Injection Parenteral Powder, for solution Intravenous 400 mg/20mL Powder, for solution Intravenous 600 mg/20mL Injection, powder, for solution Intravenous Powder, for solution Intravenous Injection, powder, for solution Intravenous 600 mg Injection, powder, for solution Intravenous 600 mg/1vial
- Not Available
Patent Number Pediatric Extension Approved Expires (estimated) Region US8247400 No 2012-08-21 2031-02-10 US6417175 No 2002-07-09 2022-04-11 US7419973 No 2008-09-02 2021-12-15 US6906055 No 2005-06-14 2021-12-15 US9629861 No 2017-04-25 2030-09-21
- Experimental Properties
Property Value Source water solubility >100 mg/ml # Steed ME, Rybak MJ: Ceftaroline: a new cephalosporin with activity against resistant gram-positive pathogens. Pharmacotherapy. 2010 Apr;30(4):375-89. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20334458
- Predicted Properties
Property Value Source Water Solubility 0.0245 mg/mL ALOGPS logP -0.79 ALOGPS logP -3.7 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 1.8 ChemAxon pKa (Strongest Basic) 0.39 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 223.24 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 171.63 m3·mol-1 ChemAxon Polarizability 63.9 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 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 - 0.9668 Blood Brain Barrier - 0.9688 Caco-2 permeable - 0.6428 P-glycoprotein substrate Substrate 0.7512 P-glycoprotein inhibitor I Non-inhibitor 0.8295 P-glycoprotein inhibitor II Inhibitor 0.556 Renal organic cation transporter Non-inhibitor 0.8255 CYP450 2C9 substrate Non-substrate 0.589 CYP450 2D6 substrate Non-substrate 0.8067 CYP450 3A4 substrate Non-substrate 0.5087 CYP450 1A2 substrate Non-inhibitor 0.6682 CYP450 2C9 inhibitor Non-inhibitor 0.6399 CYP450 2D6 inhibitor Non-inhibitor 0.8544 CYP450 2C19 inhibitor Non-inhibitor 0.6139 CYP450 3A4 inhibitor Inhibitor 0.5 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6434 Ames test Non AMES toxic 0.6505 Carcinogenicity Non-carcinogens 0.7956 Biodegradation Not ready biodegradable 0.9875 Rat acute toxicity 2.5251 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9887 hERG inhibition (predictor II) Non-inhibitor 0.7316
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key 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
Drug created on March 19, 2008 16:38 / Updated on July 29, 2021 04:17