Ceftobiprole medocaril
- Product Name
- Ceftobiprole medocaril
- CAS No.
- 376653-43-9
- Chemical Name
- Ceftobiprole medocaril
- Synonyms
- BAL5788;Valine Impurity 146;Ceftobiprole medocaril;Ceftobiprole medocaril USP/EP/BP;BAL-5788,Inhibitor,penicillin,cephalosporin,inhibit,gram-positive,pyrrolidinone,BAL 5788,MRSA,Ceftobiprole medocaril,Bacterial,vancomycin,pathogens,staphylococci,gram-negative,VRSA,methicillin,Prodrug;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(hydroxyimino)acetyl]amino]-3-[[(E,3'R)-1'-[[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy]carbonyl]-2-oxo[1;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2Z)-2-(5-aMino-1,2,4-thiadiazol-3-yl)-2-(hydroxyiMino)acetyl]aMino]-3-[[(E,3'R)-1'-[[(5-Methyl-2-oxo-1,3-dioxol-4-yl)Methoxy]carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-ylidene]Methyl]-8-oxo-,(6R,7R)-
- CBNumber
- CB21856033
- Molecular Formula
- C26H26N8O11S2
- Formula Weight
- 690.66
- MOL File
- 376653-43-9.mol
Ceftobiprole medocaril Property
- Density
- 1.95
- pka
- 2.46±0.50(Predicted)
N-Bromosuccinimide Price
- Product number
- API0016377
- Product name
- CEFTOBIPROLE MEDOCARIL
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $502.89
- Updated
- 2021/12/16
Ceftobiprole medocaril Chemical Properties,Usage,Production
Description
Ceftobiprole medocaril is a new injectable cephalosporin antibiotic with broad-spectrum activity against a wide range of difficult-to-treat Gram-positive and Gram-negative hospital- and community-acquired infections including MRSA. It was launched in Canada for the treatment of cSSSI, including diabetic foot infection. Ceftobiprole medocaril is a water-soluble pro-drug of ceftobiprole, which is a pyrrolidinone-3-ylidenemethyl cephem with a 3-pyrrolidinyl side chain. The pro-drug is derived by the attachment of a carbamoyl ester group on the pyrrolidine nitrogen of ceftobiprole. Like all beta-lactam antibiotics, ceftobiprole produces its bactericidal effects by inhibiting cell wall synthesis through the prevention of the cross-linking of peptides on the mucosaccharide chains that make up the cell wall. This is accomplished by binding to and inhibiting the penicillin-binding proteins (PBPs). As a result, bacterial cell walls are weakened and susceptible to osmotic pressure and cell lysis. The broad-spectrum activity of ceftobiprole is due to the inhibition of PBPs in both Gram-positive and Gram-negative bacteria. In addition, ceftobiprole inhibits PBP2x in penicillin-resistant Streptococcus pneumoniae as well as PBP3 and other PBPs in certain Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa.Among Gram-positive pathogens, it has excellent activity against coagulase-negative staphylococci (both methicillin-susceptible and methicillin-resistant strains), S. pneumoniae (including penicillinresistant strains) and other streptococcal species, and Enterococcus faecalis (MIC90 4 mg/mL).Ceftobiprole is also active in vitro against a broad range of aerobic Gram-negative bacilli, including P. aeruginosa, against which its activity is similar to that of cefepime.
Originator
Roche (Switzerland)
Uses
Broad spectrum antibiotic.
Definition
ChEBI: Ceftobiprole medocaril is a cephalosporin. It has a role as a prodrug.
brand name
Zeftera
Synthesis
The synthesis of ceftobiprole and
ceftobiprole medocaril have been reported in several patents
and the synthesis of the prodrug will be highlighted as shown
in Schemes 4.1-4.3. Activation of the amino dithiazole
acid salt 26 with benzothiazole disulfide 27 via
diethyl phosphite gave thioester 28 in 82% yield. Condensation
of 28 with aminocephalosporin 29 using tetramethyl
guanidine (30) as the base in DMF at 0 °C provided intermediate
acid 31, which was then immediately
esterified by reaction with diphenyl diazomethane at 0 °C to
give diphenylemethyl ester 33 in 91% yield. Alcohol 33 was
then oxidized with sodium hypochlorite in the presence of
TEMPO to give the desired aldehyde 34 in 74% yield, which
was ready to be coupled to the phosphonium salt 41.
Ceftobiprole medocaril Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Ceftobiprole medocaril manufacturers
- Product
- Ceftobiprole medocaril 376653-43-9
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 500 MT
- Release date
- 2020-05-25