5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]-
• CAS No.: 55268-75-2
• Molecular Formula: C16H16N4O8S
• Molecular Weight: 424.391
• European Community (EC) Number: 259-560-1
• Wikipedia: Cefuroxime
• ChEMBL ID: CHEMBL1620018
• Mol file: 55268-75-2.mol

Synonyms:Cefuroxime Acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]-;97232-97-8;Spectrum5_000660;BSPBio_003103;CHEMBL1620018;CHEBI:103836;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-;55268-75-2;IDI1_000159;EN300-297791;3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]-

Chemical Property:

• Appearance/Colour: White to ivory white crystalline powder
• Melting Point: 171.5-173 °C
• Refractive Index: 1.665
• PKA: pKa 2.5(H2O) (Uncertain)
• PSA: 199.06000
• Density: 1.76 g/cm³
• LogP: 0.49310
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 145mg/L at 25℃
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 424.06888465
• Heavy Atom Count: 29
• Complexity: 798

Purity/Quality:

99%min ^*data from raw suppliers

Cefuroxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-24-37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• Isomeric SMILES: CO/N=C(\C1=CC=CO1)/C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• Recent EU Clinical Trials: Evaluating the vulnerability of traditional and transposition FAMM flaps using microdialysis
• Description: Cefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
• Uses: Cefuroxime is a second-generation cephalosporin antibiotic. Antibacterial.
• Therapeutic Function: Antibiotic
• Clinical Use: It has been used successfully to treat urinary, soft-tissue and pulmonary infections, as well as septicemia, and as a single- dose treatment (with probenecid) of gonorrhea due to β-lactamase-producing strains. It has been widely used for surgical prophylaxis. Cefuroxime axetil (Ceftin) is the 1-acetyoxyethyl ester ofcefuroxime. During absorption, this acid-stable, lipophilic,oral prodrug derivative of cefuroxime is hydrolyzed to cefuroximeby intestinal and/or plasma enzymes. The axetilester provides an oral bioavailability of 35% to 50% of cefuroxime,depending on conditions. Oral absorption of theester is increased by food but decreased by antacids and histamineH2-antagonists. The latter effect may be because ofspontaneous hydrolysis of the ester in the intestine becauseof the higher pH created by these drugs. Axetil is used forthe oral treatment of non–life-threatening infections causedby bacteria that are susceptible to cefuroxime. The prodrugform permits twice-a-day dosing for such infections.

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]-

There total 16 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6a,7b(E)]]- 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: 95.0%

isocyanate de chlorosulfonyle (1189-71-5) + (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (56271-94-4) → Cefuroxime (55268-75-2)

Guidance literature:

isocyanate de chlorosulfonyle; (6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; In dimethylcarbonate; at 0 - 5 ℃;

With hydrogenchloride; water; In dimethylcarbonate; at 10 - 15 ℃; Product distribution / selectivity;

Reference yield: 86.0%

→ Cefuroxime (55268-75-2)

Guidance literature:

Reference yield: 70.5%

isocyanate de chlorosulfonyle (1189-71-5) + 3-decarbamoyl cefuroxime acid → Cefuroxime (55268-75-2)

Guidance literature:

In tetrahydrofuran; at -70 - -45 ℃; for 0.5h; Inert atmosphere;

upstream raw materials:

cefuroxime

isocyanate de chlorosulfonyle

(6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

isocyanatophosphonic dichloride

Downstream raw materials:

cefuroxime axetil

di-isopropyl ether

(6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-3-Carbamoyloxymethyl-7-{2-furan-2-yl-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 -. "Preparation method of cefuroxime acid". Paragraph 0055; 0058-0059; 0060; 0065-0066; 0067; 0072-0073. . Retrieved 2021/04/21.
• 2、 -. "Cefuroxime sodium compound prepared through advanced on-line process control technology and preparation thereof". . . Retrieved 2017/02/28.