This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Ceftobiprole medocaril is a cephalosporin indicated in the treatment of pneumonia.
- Brand Names
- Zevtera
- Generic Name
- Ceftobiprole medocaril
- DrugBank Accession Number
- DB14733
- Background
Ceftobiprole medocaril is a ceftobiprole prodrug.
- Type
- Small Molecule
- Groups
- Approved, Experimental, Investigational
- Structure
Structure for Ceftobiprole medocaril (DB14733)
- Weight
- Average: 690.66
Monoisotopic: 690.116246037 - Chemical Formula
- C26H26N8O11S2
- Synonyms
- Ceftobiprole medocaril
- Ceftobiprole medocaril free acid
Pharmacology
- Indication
Ceftobiprole medocaril is an antibacterial indicated for the treatment of adult patients with Staphylococcus aureus bloodstream infections (bacteremia) (SAB), including those with right-sided infective endocarditis.2 It is additionally indicated in adult patients with acute bacterial skin and skin structure infections (ABSSSI).2 It is indicated in adult and pediatric patients ≥3 months of age for the treatment of community-acquired bacterial pneumonia (CABP).2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute bacterial skin and skin structure infection (absssi) caused by klebsiella pneumoniae infection •••••••••••• ••••• ••••••••• Treatment of Acute bacterial skin and skin structure infection (absssi) caused by staphylococcus aureus infection •••••••••••• ••••• ••••••••• Treatment of Acute bacterial skin and skin structure infection (absssi) caused by streptococcus pyogenes infection •••••••••••• ••••• ••••••••• Treatment of Bacteremia caused by staphylococcus aureus •••••••••••• ••••• ••••••••• Treatment of Community acquired pneumonia (cap) caused by escherichia coli infection •••••••••••• •••••••••• ••••••• ••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AMecA inhibitorStaphylococcus aureus APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2X inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftobiprole medocaril. Acenocoumarol The risk or severity of bleeding can be increased when Ceftobiprole medocaril is combined with Acenocoumarol. Alteplase The therapeutic efficacy of Alteplase can be decreased when used in combination with Ceftobiprole medocaril. Ambrisentan The serum concentration of Ambrisentan can be increased when it is combined with Ceftobiprole medocaril. Ambroxol The risk or severity of methemoglobinemia can be increased when Ceftobiprole medocaril is combined with Ambroxol. - Food Interactions
- Not Available
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 Ceftobiprole medocaril sodium N99027V28J 252188-71-9 MFAWUGGPPMTWPU-LCJFHXTKSA-M - Active Moieties
Name Kind UNII CAS InChI Key Ceftobiprole prodrug 5T97333YZK 209467-52-7 VOAZJEPQLGBXGO-SDAWRPRTSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Zeftera Powder, for solution 500 mg / vial Intravenous Janssen Pharmaceuticals 2008-09-02 2010-04-23 Canada 
Zevtera Powder, for solution 500 mg / vial Intravenous Avir Pharma Inc. 2018-03-20 Not applicable Canada
Categories
- ATC Codes
- J01DI01 — Ceftobiprole medocaril
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- YXV28V1B07
- CAS number
- 376653-43-9
- InChI Key
- HFTSMHTWUFCYMJ-YIOMYIDASA-N
- InChI
- InChI=1S/C26H26N8O11S2/c1-10-14(45-26(41)44-10)8-43-25(40)32-4-3-13(7-32)33-5-2-11(20(33)36)6-12-9-46-22-16(21(37)34(22)17(12)23(38)39)28-19(35)15(30-42)18-29-24(27)47-31-18/h6,13,16,22,42H,2-5,7-9H2,1H3,(H,28,35)(H,38,39)(H2,27,29,31)/b11-6+,30-15-/t13-,16-,22-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(N-hydroxyimino)acetamido]-3-{[(3E,3'R)-1'-{[(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methoxy]carbonyl}-2-oxo-[1,3'-bipyrrolidin]-3-ylidene]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@@]1(NC(=O)C(=N/O)\C2=NSC(N)=N2)C(=O)N2C(C(O)=O)=C(CS[C@]12[H])\C=C1/CCN(C1=O)[C@]1([H])CCN(C1)C(=O)OCC1=C(C)OC(=O)O1
References
- General References
- AIFA Product Information: MABELIO (ceftobiprole medocaril) injection [Link]
- FDA Approved Drug Products: Zevtera (ceftobiprole medocaril sodium) injection for intravenous use [Link]
- FDA Press Announcement: FDA Approves New Antibiotic for Three Different Uses [Link]
- EMA Refusal Assessment Report: Zeftera [Link]
- Health Canada Product Monograph: Zevtera (ceftobiprole medocaril sodium) for intravenous injection [Link]
- External Links
- ChemSpider
- 28475342
- ChEBI
- 135968
- Wikipedia
- Ceftobiprole
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Acute Bacterial Skin and Skin Structure Infection (ABSSSI) 1 3 Completed Treatment Bacteremia caused by Staphylococcus Aureus 1 3 Completed Treatment Bacterial skin infections / Skin Diseases, Infectious / Staphylococcal Skin Infections 2 3 Completed Treatment Community Acquired Pneumonia (CAP) / Hospital-Acquired Pneumonia 1 3 Completed Treatment Pneumonia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Parenteral 500 MG Powder, for solution Intravenous 500 mg / vial Solution Intravenous 666.60 mg Powder Intravenous 666.6 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.131 mg/mL ALOGPS logP 0.16 ALOGPS logP -0.97 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 3.19 Chemaxon pKa (Strongest Basic) 0.43 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 256.48 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 163.59 m3·mol-1 Chemaxon Polarizability 64.88 Å3 Chemaxon Number of Rings 6 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Per prescribing information: "Ceftobiprole has a high affinity for S. aureus PBPs 1 – 4, including PBP2a in methicillin-resistant Staphylococcus aureus."
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Not Available
- Gene Name
- mecA
- Uniprot ID
- Q7DHH4
- Uniprot Name
- MecA
- Molecular Weight
- 76102.075 Da
References
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Per prescribing information: "Ceftobiprole has a high affinity for ... PBP2x and PBP2b in penicillin-resistant Streptococcus pneumoniae."
- 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
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Per prescribing information: "Ceftobiprole has a high affinity for ... PBP2x and PBP2b in penicillin-resistant Streptococcus pneumoniae."
- General Function
- Penicillin binding
- Specific Function
- Penicillin-binding proteins (PBPs) function in the late steps of murein biosynthesis. Beta-lactams inactivate the PBPs by acylating an essential serine residue in the active site of these proteins.
- Gene Name
- pbpX
- Uniprot ID
- P59676
- Uniprot Name
- Penicillin-binding protein 2X
- Molecular Weight
- 82342.565 Da
References
Drug created at January 27, 2019 21:57 / Updated at April 19, 2024 20:55