1192500-31-4 Usage
Description
AfibactaM, also known as (2S,5R)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide, is a member of the azabicycloalkanes class. It is characterized by the replacement of the amino hydrogen at position 6 with a sulfooxy group. AvibactaM is used in combination with ceftazidime pentahydrate and is primarily known for its pharmaceutical applications.
Uses
Used in Pharmaceutical Industry:
AfibactaM is used as an additive for ceftazidime pentahydrate, a type of antibiotic, to enhance its effectiveness against bacterial infections. The combination of AvibactaM and ceftazidime pentahydrate is particularly effective in treating complicated urinary tract infections, including pyelonephritis. This application takes advantage of AvibactaM's ability to improve the antibiotic's efficacy and overcome bacterial resistance.
Enzyme inhibitor
This non-β-lactam inhibitor of β-lactamase (FW = 261.27 g/mol; CAS 1192500-31-4), also known as NLX104 and AVE1330A, shows a spectrum of action against Classes A and C β-lactamase as well as selected Class D β-lactamase, enzymes that often confer resistance to β-lactam antibiotics. By forming a high-affinity complex with its target enzymes, avibactam enhances the antibacterial activity of certain β-lactam drugs, such as ceftaroline. With over 1000 known β-lactamase, the action of avibactam is apt to depend on the invidual active-site interactions. Mode of Action: Acylation and deacylation rates have been measured for the clinically important enzymes CTX-M-15, KPC-2, E. cloacae AmpC, P. aeruginosa AmpC, OXA-10, and OXA-48. The efficiency of acylation (kon/Ki) varies across the enzyme spectrum, from 1.1 x 101 M–1 s –1 for OXA-10 to 1.0 x 105 M–1 s –1 for CTX-M-15. Inhibition of OXA-10 was shown to follow a reversible covalent mechanism (see below), and the acylated OXA-10 displayed the longest residence time for deacylation, with a half-life of greater than 5 days. The inhibited enzyme forms are stable to hydrolysis for all enzymes with the exception of KPC-2, which displays slow hydrolytic route that involved fragmentation of the acyl-avibactam complex. In the case of TEM-1 lactamase, avibactam slowly covalently acylates its target, and the acylated enzyme subsequently undergoes slow deacylation (koff = 0.045 min?1 ) regenerating avibactam intact. Use as a Combined Drug: Combination of avibactim with extended-spectrum cephalosporins or aztreonam shows promise in inhibiting Klebsiella pneumoniae (KP) isolates harboring carbapenemases, or KPCs. Given abundant experience with ceftazidime and the significant improvement avibactam provides against contemporary β-lactamase-producing Gram-negative pathogens, this combination will likely play a role in the treatment of complicated urinary tract infections (as monotherapy) and complicated intra-abdominal infections (in combination with metronidazole) caused (or suspected to be caused) by otherwise resistant pathogens, such as extended spectrum β-lactamase-, AmpC-, or Klebsiella pneumoniae carbapenemase producing Enterobacteriaceae and multidrug-resistant P. aeruginosa.
Check Digit Verification of cas no
The CAS Registry Mumber 1192500-31-4 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,1,9,2,5,0 and 0 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1192500-31:
(9*1)+(8*1)+(7*9)+(6*2)+(5*5)+(4*0)+(3*0)+(2*3)+(1*1)=124
124 % 10 = 4
So 1192500-31-4 is a valid CAS Registry Number.
1192500-31-4Relevant articles and documents
Method for synthesize Avibactam key intermediate (S)-N-t-butyloxycarboryl pyroglutamic acid-2-benzyl ester and recrystallization process of Avibactam key intermediate
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Paragraph 0011-0014, (2019/10/04)
The invention discloses a one-step method for synthesize Avibactam key intermediate (S)-N-t-butyloxycarboryl pyroglutamic acid-2-benzyl ester and a recrystallization process of the Avibactam key intermediate. L-pyroglutamic acid is taken as a raw material to synthesize faint yellow (S)-N-tert-butyloxycarboryl pyroglutamic acid-2-benzyl ester by one step, and recrystallizing is carried out to obtain white (S)-N-t-butyloxycarboryl pyroglutamic acid-2-benzyl ester, wherein the purity is 99% or above, and the yield is 95% or above. The method is mild in reaction condition and simple in operation and is green and efficient, the product is stable, a next-step reaction is facilitated, and industrial production is facilitated.
AVIBACTAM FREE ACID
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Page/Page column 25; 26; 27; 28, (2018/03/25)
The present invention relates to avibactam free acid, a method for preparing avibactam free acid and a method for preparing avibactam sodium by further reacting avibactam free acid. The invention further refers to a pharmaceutical composition comprising avibactam free acid, one or more alkaline sodium salt(s) and one or more beta-lactam antibiotic(s). The pharmaceutical composition of the present invention can be used as medicament, in particular for treatment and/or prevention of bacterial infections.
Method for synthesizing beta-lactamase inhibitor Avibactam
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, (2017/07/22)
The invention relates to a method for synthesizing a beta-lactamase inhibitor Avibactam and belongs to the technical field of preparation of beta-lactamase inhibitors. The method disclosed by the invention comprises the following steps: (1) taking a compound 2 as a raw material, and reacting with RNH2 so as to produce a compound 3; (2) enabling the compound 3 and a biocatalyst to produce a compound 4 in an organic solvent in the presence of glucose or sucrose; (3) enabling the compound 4 to react with trifluoroacetic anhydride so as to obtain a compound 5; (4) enabling the compound 5 to react with RONH2 so as to produce a compound 6; (5) hydrolyzing the compound 6 under alkaline conditions so as to produce a compound 7; (6) enabling the compound 7 to react with triphosgene so as to produce a compound 8; (7) enabling the compound 8 to react with ammonium formate in the presence of a catalyst so as to produce a compound 9 in the organic solvent, wherein the catalyst is a Pd/C system; and (8) enabling the compound 9 to react with a sulfonating agent, thereby obtaining the product 1. The method disclosed by the invention is stable in process, high in yield, simple and safe in operation and low in production cost.