Ceftobiprole medocaril sodiumProduct ingredient for Ceftobiprole medocaril
- Name
- Ceftobiprole medocaril sodium
- Drug Entry
- Ceftobiprole medocaril
Ceftobiprole medocaril is a prodrug of ceftobiprole, a fifth-generation semisynthetic cephalosporin antibacterial. Ceftobiprole is a broad-spectrum agent with demonstrated activity against both Gram-positive and Gram-negative bacteria, including antibiotic-resistant strains of Staphylcoccus aureus (methicillin-resistant Staphylococcus aureus; MRSA).
The EMA's Committee for Medicinal Products for Human Use (CHMP) adopted a negative opinion of ceftobiprole medocaril in February 2010, recommending the refusal of its marketing authorization in the European Union primarily due to data quality issues in pivotal clinical studies.4 It received its first approval in Canada in October 2017 for use in certain patients with bacterial pneumonia,5 and was subsequently approved in the United States with additional indications for skin and skin structure infections and bacteremia in April 2024.2,3
- Accession Number
- DBSALT002833
- Structure
Structure for Ceftobiprole medocaril sodium (DBSALT002833)
- Synonyms
- Ceftobiprol medocaril sodium
- External IDs
- BAL-5788 / BAL-5788-001 / BAL5788 / BAL5788-001 / RO 65-5788 / RO-65-5788 / RO-655788
- UNII
- N99027V28J
- CAS Number
- 252188-71-9
- Weight
- Average: 712.64
Monoisotopic: 712.09819029 - Chemical Formula
- C26H25N8NaO11S2
- InChI Key
- MFAWUGGPPMTWPU-LCJFHXTKSA-M
- InChI
- InChI=1S/C26H26N8O11S2.Na/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);/q;+1/p-1/b11-6+,30-15-;/t13-,16-,22-;/m1./s1
- IUPAC Name
- sodium (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-carboxylate
- SMILES
- [Na+].[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
- External Links
- ChemSpider
- 30791463
- Predicted Properties
Property Value Source Water Solubility 0.111 mg/mL ALOGPS logP 0.64 ALOGPS logP -0.97 Chemaxon logS -3.8 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 3 Chemaxon Polar Surface Area 259.31 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 174.43 m3·mol-1 Chemaxon Polarizability 65.75 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