4052-54-4

Usage

Uses

Used in Pharmaceutical Industry:
[2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is used as an antibiotic for the treatment of various bacterial infections. Its ability to interfere with bacterial cell wall synthesis makes it a valuable compound in combating resistant strains of bacteria and providing effective treatment options for patients.
Used in Research and Development:
In the field of medical research, [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide serves as a valuable tool for studying the mechanisms of bacterial resistance to antibiotics and the development of new drugs to combat antibiotic-resistant infections. Its unique structure and properties can be further explored to design more effective and targeted antibiotics with fewer side effects.
Used in Drug Delivery Systems:
Similar to other antibiotics, [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide can be incorporated into drug delivery systems to improve its bioavailability, targeting, and overall therapeutic efficacy. This may involve the use of nanoparticles, liposomes, or other advanced drug delivery technologies to enhance the compound's performance in treating bacterial infections.

InChI:InChI=1/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24(16)23)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-,24?/m1/s1

Upstream product

• 40578-79-8 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid methyl ester 
• 4052-68-0 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid benzyl ester 
• 113-98-4 Penicillin G potassium 
• 653-89-4 penicillin G methyl ester 
• 1254-56-4 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 61-33-6 penicillin G 
• 39906-59-7 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid; potassium salt 
• 99673-35-5 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid cyanomethyl ester 
• 51446-87-8 diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide 

Downstream Products

• 101833-98-1 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid benzhydryl ester 
• 121894-91-5 (2S,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid phenylacetoxymethyl ester 
• 121894-92-6 (R)-3-Methyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid phenylacetoxymethyl ester 
• 121894-93-7 (R)-3-Methoxy-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid phenylacetoxymethyl ester 
• 27255-72-7 7-phenylacetamidodesacetoxycephalosporanic acid 
• 130164-50-0 (R)-2-{(2R,3R)-2-[(2R,3R)-1-((R)-1-Benzhydryloxycarbonyl-2-methyl-propyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-butyric acid benzhydryl ester 
• 130164-51-1 (R)-2-{(2R,3R)-2-[(2R,3R)-1-((R)-1-Carboxy-2-methyl-propyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-butyric acid 
• 130164-49-7 (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-butyric acid benzhydryl ester 
• 119944-09-1 (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzhydryl ester 
• 79386-26-8 methyl 2-<(3S)-4-(benzothiazol-2-ylthio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-2-enoate 
• 79434-35-8 methyl (2R)-2-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-3-enoate 
• 79386-27-9 (1S,5R)-3-phenylmethyl-6-<(1R)-1-carboxy-2-methylprop-2-enyl>-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one 
• 79386-29-1 1-dethia-1-oxa-5-epi-anhydropenicillin 
• 79386-28-0 (2R,5S,6S)-2-(1-methylethenyl)-6-phenylacetamido-4-oxa-1-azabicyclo<3.2.0>heptane-3,7-dione 

Relevant academic research and scientific papers

Study on crystal morphology of penicillin sulfoxide in different solvents using binding energy

The binding energy of the solvent is an important factor in crystal morphology. In this study, binding energies of water, ethyl acetate, and butyl acetate on specific surfaces of penicillin sulfoxide were evaluated. Molecular modeling techniques based on the adsorption of solvent molecules on specific crystal surfaces were utilized to determine the binding energies. Our results show a strong association between the absolute value of the binding energy and crystallization. The results predicted by molecular modeling are well-fitted with experimental results. Efficient solvent selection and production process optimization were successfully achieved by using the methodology developed in this paper. Our study illustrates a novel strategy that can be used for the investigation of solvent effects.

Selective oxidation of penicillin G with hydrogen peroxide and with enzymatically generated peroxyoctanoic acid

Two convenient procedures for the oxidation of penicillin G into penicillin G 1-(s)-oxide have been developed.Both the mild oxidation with enzymatically generated peroxyoctanoic acid and the attractive and simple oxidation with the sole use of hydrogen peroxide are valuable alternatives for the commercial oxidation with 40percent peroxyacetic acid.

Industrial production method for preparing penicillin sulfoxide by continuously oxidizing penicillin

The invention discloses an industrial production method for preparing penicillin sulfoxide by continuously oxidizing penicillin, and belongs to the field of pharmaceutical chemicals; a continuous reaction method is adopted, a penicillin solution and peracetic acid or other oxidants simultaneously flow into a mixer or a microreactor according to a certain proportion, and a penicillin sulfoxide solution is obtained by reaction at high temperature and in short time; the method can be used for an oxidation process of a process for preparing penicillin sulfoxide by taking penicillin fermentation liquor, filtrate, BA, RB, penicillin industrial salt and the like as initial raw materials, and solves the problem that the reaction temperature and the reaction time are influenced by mass transfer and low heat transfer efficiency of batch reaction; therefore, the problems of poor reaction liquid quality and low reaction yield are solved, and the yield of penicillin sulfoxide is high.

Determination of optimal operation conditions for production of cephalosporin g from penicillin g potassium

Cephalosporin G (Ceph-G) is one of the most important components for producing β-lactam antibiotics. It is also a starting material for the synthesis of cephalosporin antibiotics. Ceph-G was produced from penicillin G potassium (Pen-G.K.) during multiple steps consisting of conversion of Pen-G.K. to penicillin G sulfoxide followed by dehydration and ring expansion to produce Ceph-G. In this work, the amount of all starting materials and stoichiometric ratios were balanced, and the optimum values were determined. In addition, the process was optimized to evaluate the parameters affecting the scale-up of our test apparatus from laboratory to pilot scale. Difficulties for the industrial production of Ceph-G have been considered, and the production cost has been considerably decreased. In this research, Ceph-G with high purity more than 98% and high yield more than 94% was obtained.