Ceftobiprole medocaril

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCommunity acquired pneumonia (cap) caused by escherichia coli infection•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofCommunity acquired pneumonia (cap) caused by haemophilus influenzae infections•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofCommunity acquired pneumonia (cap) caused by klebsiella pneumoniae infection•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofCommunity acquired pneumonia (cap) caused by staphylococcus aureus infection•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofCommunity acquired pneumonia (cap) caused by streptococcus pneumoniae infections•••••••••••••••••••••• ••••••• ••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
DrugInteraction
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftobiprole medocaril.
AcenocoumarolThe risk or severity of bleeding can be increased when Ceftobiprole medocaril is combined with Acenocoumarol.
AlteplaseThe therapeutic efficacy of Alteplase can be decreased when used in combination with Ceftobiprole medocaril.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Ceftobiprole medocaril.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Ceftobiprole medocaril is combined with Ambroxol.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ceftobiprole medocaril sodiumN99027V28J252188-71-9MFAWUGGPPMTWPU-LCJFHXTKSA-M
Active Moieties
NameKindUNIICASInChI Key
Ceftobiproleprodrug5T97333YZK209467-52-7VOAZJEPQLGBXGO-SDAWRPRTSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ZefteraPowder, for solution500 mg / vialIntravenousJanssen Pharmaceuticals2008-09-022010-04-23Canada flag
ZevteraPowder, for solution500 mg / vialIntravenousAvir Pharma Inc.2018-03-20Not applicableCanada flag

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
  1. AIFA Product Information: MABELIO (ceftobiprole medocaril) injection [Link]
  2. FDA Approved Drug Products: Zevtera (ceftobiprole medocaril sodium) injection for intravenous use [Link]
  3. FDA Press Announcement: FDA Approves New Antibiotic for Three Different Uses [Link]
  4. EMA Refusal Assessment Report: Zeftera [Link]
  5. Health Canada Product Monograph: Zevtera (ceftobiprole medocaril sodium) for intravenous injection [Link]
ChemSpider
28475342
ChEBI
135968
Wikipedia
Ceftobiprole

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionParenteral500 MG
Powder, for solutionIntravenous500 mg / vial
PowderIntravenous666.6 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.131 mg/mLALOGPS
logP0.16ALOGPS
logP-0.97Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.19Chemaxon
pKa (Strongest Basic)0.43Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area256.48 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity163.59 m3·mol-1Chemaxon
Polarizability64.88 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0010029000-99f100987443676c27c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0191004000-13040711cbaba7bf712e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0040039000-c8c9d13f4268250adb61
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-1000319000-95fd1a701cc6ea6e0f5d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w2d-0340198000-b39905fc15af54b4b873
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-5900238000-3cb34542392133daec57
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at January 27, 2019 21:57 / Updated at April 14, 2024 23:44