7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 88040-23-7
• Molecular Formula: C19H24N6O5S2
• Molecular Weight: 480.569
• Hs Code.: 29419000
• European Community (EC) Number: 643-019-5
• Wikipedia: Cefepime
• Mol file: 88040-23-7.mol

Synonyms:88040-23-7;7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;C19-H24-N6-O5-S2;C6H14N4O2.C19H24N6O5S2.2ClH;C6-H14-N4-O2.C19-H24-N6-O5-S2.2Cl-H;CID 2622;FT-0603052

Chemical Property of 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Appearance/Colour: colorless powder
• Melting Point: 150 °C
• PSA: 203.58000
• LogP: -0.41110
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 480.12496023
• Heavy Atom Count: 32
• Complexity: 869

Purity/Quality:

99% ^*data from raw suppliers

Cefepime 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(CCCC1)CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)[O-]
• Recent EU Clinical Trials: Efficacy and safety of different antimicrobial DURATions for the treatment of infections associated with Osteosynthesis
• Recent NIPH Clinical Trials: A Phase II Study of Cefepime Monotherapy for Febrile Neutropenia in Patients with Lung Cancer
• Description: Cefepime is a new fourth-generation parenteral cephalosporine antibiotic launched in 1993 in Sweden and France. Cefepime has broad spectrum antimicrobial activity against Staphylococcus, Strepfococcus, Pseudomonas, and the Enterobacteriaceae, including many bacterial isolates that are resistant to commonly used ceftazidime and cefotaxime. Its efficacy has been demonstrated in the treatment of lower respiratory tract infections especially pneumonia, intra-abdominal and urinary tract infections, skin and soft tissue infections, chronic osteomyelitis and in prophylaxis of biliary tract and prostate infections. It is well tolerated by patients and is reported to exhibit no significant drug interactions.
• Uses: Cefepime is used for bacterial infections caused by microorganisms that are sensitive to drugs in septicemia, bacteriemia, complicated infections of the upper and lower sections of the urinary system, pneumonia, pulmonary abscesses, emphysema of the pleura, fever in patients with neutropenia, and infected skin and soft tissue wounds. Synonyms of this drug are maxipime, cepim, cepimex, and others.
• Therapeutic Function: Antibiotic
• Clinical Use: Cefepime (Maxipime, Axepin) is a parenteral, β-lactamase–resistant cephalosporin that is chemically and microbiologicallysimilar to cefpirome. It also has a broadantibacterial spectrum, with significant activity against bothGram-positive and Gram-negative bacteria, including streptococci,staphylococci, Pseudomonas spp., and theEnterobacteriaceae. It is active against some bacterial isolatesthat are resistant to ceftazidime. The efficacy of cefepimehas been demonstrated in the treatment of urinary tract infections,lower respiratory tract infections, skin and soft tissueinfections, chronic osteomyelitis, and intra-abdominal andbiliary infections. It is excreted in the urine with a half-life of2.1 hours. It is bound minimally to plasma proteins. Cefepimeis also a fourth-generation cephalosporin. Proprietary name: Maxipime. Preparation: Injection. Dosage: Adult, i.m., i.v., 1–6 g per day in 2–3 divided doses. Available in USA, most of Europe and Japan; not available in the UK.

Technology Process of 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 1 articles about 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ cefepime (88040-23-7)

Guidance literature:

Reference yield: 85.0%

p-toluenesulfonyl chloride (98-59-9) + cefepime (88040-23-7) → (6R,7R)-7-((Z)-2-(methoxyimino)-2-(2-(4-methylphenylsulfonamido)thiazol-4-yl)acetamido)-3-((1-methylpyrrolidin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:

With sodium carbonate; In water; at 35 ℃; pH=8 - 10;

DOI:10.4314/bcse.v31i3.13

Reference yield: 40.0%

cefepime (88040-23-7) → (6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(methoxyimino)acetamido]-3-[(1-methyl-1-pyrrolidinium)methyl]-2-cephem-4-carboxylate (88040-25-9)

Guidance literature:

cefepime; With N-Trimethylsilylacetamide; In dichloromethane; for 0.5h;

With triethylamine; In dichloromethane; at 25 - 30 ℃; for 24h;

With hydrogenchloride; at 2 - 5 ℃; Further stages.;

Downstream raw materials:

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(methoxyimino)acetamido]-3-[(1-methyl-1-pyrrolidinium)methyl]-2-cephem-4-carboxylate

Refernces