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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
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Ceftobiprole medocaril Property

Density 
1.95
pka
2.46±0.50(Predicted)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0016377
Product name
CEFTOBIPROLE MEDOCARIL
Purity
95.00%
Packaging
5MG
Price
$502.89
Updated
2021/12/16
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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. The preparation of phosphonate 41 is described in Scheme 4.2 and was initiated by the reaction of amino pyrrolidine 35 with acid chloride 36 with 50% sodium hydroxide in DCM to provide the amidopyrrolidine 37 in quantitative yield. Bromide 37 was then treated with triphenylphosphine to give phosphonate 38 in 78% yield. Removal of the allyl carbonate protecting group was accomplished through reaction with tributyltin hydride with palladium catalysis to afford bipyrrolidine 39, which was then treated with the carbonate 40 to give phosphonium salt 41 in 26% yield, which was now activated for Wittig condensation with aldehyde 34. The completion of the preparation of ceftobiprole medocaril is described in the scheme. Phosphonate 41 was deprotonated with potassium t-butoxide to generate the corresponding ylide that was subsequently reacted with the cephalosporin aldehyde 34 to produce the olefinic betalactam ester 42 in 29% yield. Removal of the diphenylmethyl ester and trityl groups were accomplished by reaction with triethylsilane in the presence of TFA completing the synthesis of ceftobiprole medocaril (IV) in 92% yield.< style="text-align: center;">

Ceftobiprole medocaril Preparation Products And Raw materials

Raw materials

Preparation Products

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Ceftobiprole medocaril Suppliers

AdooQ Bioscience CHINA
Tel
025-58849295 18951903616;
Fax
025-68650336
Email
info@adooq.cn
Country
China
ProdList
2989
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60
Struchem Co., Ltd.
Tel
0512-0512-63009836 15365350169
Fax
0512-63006936
Email
helen@struchem.com
Country
China
ProdList
3988
Advantage
60
Shanghai Synchem Pharma Co., ltd
Tel
21-619849051-1 18521059765
Email
synchempharma@aliyun.com
Country
China
ProdList
6456
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55
ShangHai Biochempartner Co.,Ltd
Tel
17754423994 17754423994
Fax
QQ:2853530913
Email
2853530910@QQ.com
Country
China
ProdList
8011
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62
Jinan Guoding Pharmaceutical Technology Co., Ltd.
Tel
15628878003
Fax
053167801621
Email
sales@guodingpharma.com
Country
China
ProdList
481
Advantage
58
Shaanxi Dideu Medichem Co. Ltd
Tel
+86-029-89586680 +86-18192503167
Fax
+86-29-88380327
Email
1026@dideu.com
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China
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9128
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58
Changzhou Chenhong Biotechnology Co., Ltd.
Tel
0519-85788828 13775037613
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sales@chemrenpharm.com
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China
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3574
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Absin Bioscience Inc.
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021-38015121 15000105423
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chenjw@absin.cn
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China
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24734
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58
Wuhan Topule
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+86-02787215551 +86-19945035818
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027-87215551
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2936752263@qq.com
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China
ProdList
8310
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Hubei Kele Fine Chemical Co., Ltd
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027-59101668 19945030958
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027-59101668
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2881924765@qq.com
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China
ProdList
7973
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58
Wuhan Augda Biotechnology Co., Ltd
Tel
15071299552
Fax
QQ:262933239
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262933239@qq.com
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China
ProdList
6637
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58
Shanghai Weishukur Medical Technology Co., LTD
Tel
15250615384
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316228842@qq.com
Country
China
ProdList
313
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Wuhan Yingnuo Pharmaceutical Technology Co., Ltd.
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+86-027-59232304 15387063101
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TargetMol Chemicals Inc.
Tel
4008200310
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marketing@tsbiochem.com
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China
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Hubei Enxing Biotechnology Co., Ltd
Tel
16621771607
Email
exbio_tech@163.com
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China
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8339
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Shandong Mopai Biotechnology Co., Ltd
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13053322091 13053322091
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admin@mopaikeji.com
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10974
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guoyungurui
Tel
18162595016
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Nanjing Shizhou Biology Technology Co.,Ltd
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025-85560043 15850508050
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Shanghai jerryxing Biomedical Technology Co., Ltd
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RD International Technology Co., Limited
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Olix (Shanghai) Pharmaceutical Technology Co., Ltd
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Zibo Hangyu Biotechnology Development Co., Ltd
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Wuhan Topule Biopharmaceutical Co., Ltd
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GIHI CHEMICALS CO.,LIMITED
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Biochempartner
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967
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View Lastest Price from Ceftobiprole medocaril manufacturers

Shaanxi Dideu Medichem Co. Ltd
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

376653-43-9, Ceftobiprole medocarilRelated Search:


  • Ceftobiprole medocaril
  • 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)-
  • BAL5788
  • Ceftobiprole medocaril USP/EP/BP
  • 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
  • BAL-5788,Inhibitor,penicillin,cephalosporin,inhibit,gram-positive,pyrrolidinone,BAL 5788,MRSA,Ceftobiprole medocaril,Bacterial,vancomycin,pathogens,staphylococci,gram-negative,VRSA,methicillin,Prodrug
  • Valine Impurity 146
  • 376653-43-9
  • C26H26N8O11S2