68373-14-8 Usage
Description
Sulbactam is prepared by partial chemical synthesis from
penicillins. The oxidation of the sulfur atom to a sulfone greatly enhances the potency of sulbactam. The
combination of sulbactam and ampicillin (Unasyn) is now clinically popular.
Originator
Sulbactam-Sodium,Antibiotic Co.,Bulgaria
Uses
Different sources of media describe the Uses of 68373-14-8 differently. You can refer to the following data:
1. antidepressant, dopamine uptake inhibitor
2. Sulbactam sodium is a semi-synthetic penem antibiotic formed by the oxidation of penicillanic acid to its sulfone and was invented by Barth at Pfizer in 1978. Sulbactam sodium is a weak antibiotic but its action as an irreversible inhibitor of β-lactamase is exploited to block the degradation of other penicillin derivatives. Sulbactam acts as a synergist with cephalosporins and penicillins against Gram positive bacteria and is used commercially in combination with ampicillin.
3. A β-lactamase inhibitor.
Manufacturing Process
Sulbactam sodium is semi-synthetic antibiotic of penicillinic group. Start
material for it's synthesis is 6-aminopenicillanic acid. First 6-aminopenicillanic
acid was isolated in 1957 year from benzylpenicilline as resalt of treating of it
by penicillinaze. Benzylpenicilline is produced by microorganism of genus
Streptomyces.Further, 6-aminopenicillanic acid reacted with bromine, hydrochloric acid and
NaNO2. As a result the 6,6-dibromopenicillanic acid was obtained.6,6-Dibromopenicillanic acid was oxidized by KMnO4, to give 6,6-dibromo-1,1-The 6,6-dibromo-1,1-dioxopenicillanic acid in presence of Fe was converted to
the 1,1-dioxopenicillanic acid (sulbactam acid). The sulbactam acid was
treated by sodium 2-ethylhexanoate and crude sulbactam sodium was
obtained.
Antimicrobial activity
Sulbactam has very weak antimicrobial activity against most
bacteria. Its only notable activity is against N. gonorrhoeae,
N. meningitidis and Acinetobacter baumannii.
Clinical Use
Sulbactam is penicillanic acid sulfone or 1,1-dioxopenicillanicacid. This synthetic penicillin derivative is a potent inhibitorof S. aureus β-lactamase as well as many β-lactamaseselaborated by Gram-negative bacilli. Sulbactam has weak intrinsicantibacterial activity but potentiates the activity ofampicillin and carbenicillin against β-lactamase–producingS. aureus and members of the Enterobacteriaceae family. Itdoes not, however, synergize with either carbenicillin or ticarcillinagainst P. aeruginosa strains resistant to these agents.Failure of sulbactam to penetrate the cell envelope is a possibleexplanation for the lack of synergy.Fixed-dose combinations of ampicillin sodium and sulbactamsodium, marketed under the trade name Unasyn assterile powders for injection, have been approved for use inthe United States. These combinations are recommended forthe treatment of skin, tissue, intra-abdominal, and gynecologicalinfections caused by β-lactamase–producing strainsof S. aureus, E. coli, Klebsiella spp., P. mirabilis, B. fragilis,and Enterobacter and Acinetobacter spp.
Check Digit Verification of cas no
The CAS Registry Mumber 68373-14-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,3,7 and 3 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 68373-14:
(7*6)+(6*8)+(5*3)+(4*7)+(3*3)+(2*1)+(1*4)=148
148 % 10 = 8
So 68373-14-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m0/s1
68373-14-8Relevant articles and documents
Synthesis method and application of amoxicillin and sulbactam hybrid molecule
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Paragraph 0072-0074; 0085-0087; 0098-0100, (2021/05/01)
The invention discloses a synthesis method and application of an amoxicillin and sulbactam hybrid molecule, and belongs to the technical field of organic synthesis. According to the method, chlorobromomethane is used as a chloromethyl reagent of sulbactam acid, so that the yield of a key intermediate sulbactam chloromethyl ester is effectively increased, and sulbactam chloromethyl ester and (Z)-6-(2-(4-hydroxyphenyl)-2-((4-methoxy-4-oxobutyl-2-ene-2-yl) amino) acetamido)-3, 3'-dihydroxyl-7-oxo-4-sulfo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid as a raw material to carry out condensation reaction, and a protecting group is removed by using strong acid, so as to prepare the amoxicillin and sulbactam hybrid molecule. The synthesis method has the advantages of mild reaction conditions, cheap and easily available raw materials, low preparation cost, good safety, simple and feasible process and high product yield.
Synthesis method of sulbactam
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, (2020/11/02)
The invention relates to a synthesis method of sulbactam, and belongs to the field of beta-lactamase inhibitor synthesis. In the method, 6-aminopenicillanic acid (6-APA) as a raw material is dissolvedin an organic solvent, and is adopted together with bromine as substrates under a strong acid condition, 6,6-dibromo penicillanic acid is formed through diazotization bromination in a manner of dropwise adding a sodium nitrite solution, and then one-step oxidation and reduction are performed to obtain sulbactam. According to the method, a hydrogen peroxide one-step oxidation mode is adopted, andthe use of potassium permanganate is avoided from the source, so that the generation of waste salt is reduced, and meanwhile, the use of a large amount of ethyl acetate is avoided. The method not onlyreduces the emission of three wastes from the source and greatly reduces the emission of organic matters and waste salt in the original process, but also greatly reduces the side reaction and the rawmaterial cost.
Extends the batanbatan acid synthesis method (by machine translation)
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, (2019/03/31)
The present invention relates to the field of drug synthesis, directed to the problem of low yield synthesis mode, provides a method of synthesizing extends the batanbatan acid, comprises the following steps: S1, diazotization and bromination reaction: in the 6 - amino penicillanic acid bromine is added in, the dilute sulfuric acid solution and sodium nitrite solid, dilute sulfuric acid concentration of the solution is 20% - 25%, to obtain the 1st intermediate; S2, oxidation reaction: to the 1st intermediate dropping potassium permanganate and dilute sulfuric acid solution, the concentration of the dilute sulfuric acid solution is 20% - 25%; S3, hydrogenation reaction: to the 2nd intermediate [...] and in dilute sulfuric acid solution, to obtain the extends the batanbatan acid. By using the 20% - 25% of the dilute sulfuric acid solution react, help to improve the diazo and bromination reaction and oxidation reaction of the active, so that the reactant more completely, thus help to improve the diazo and bromination reaction and oxidation of the yield of the reaction, and then make the overall yield of the reaction. (by machine translation)