Avibactam Sodium Salt - CAS 1192491-61-4
Catalog number: B0084-465274
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C7H10N3NaO6S
Molecular Weight:
287.23
COA:
Certificate of Analysis-Avibactam Sodium Salt 1192491-61-4 B16MW03281  
Targets:
Antibacterial
Description:
Avibactam Sodium Salt, a novel non-ᵦ-lactam ᵦ-lactamase inhibitor, binds covalently to Ambler class A ᵦ-lactamases, including KPCs, Ambler class C and some class D b-lactamases. In combination with ceftazidime, Avibactam is a new drug application for avibactam , and was approved by the FDA on February 25, 2015, to treat complicated urinary tract and complicated intra-abdominal Infections caused by antibiotic resistant-pathogens. Avibactam has limited intrinsic antimicrobial activity but restores the in vitro activity of b-lactams including ceftazidime, ceftaroline, the active metabolite of ceftaroline fosamil, and aztreonam against ESBL-producing pathogens.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-465274 500 mg $299 In stock
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Related CAS:
1192500-31-4 (free acid)
Appearance:
Solid powder
Synonyms:
sodium (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[321]octan-6-yl sulfate; NXL104; NXL-104; NXL 104; Avibactam; Avibactam sodium
Solubility:
Soluble in DMSO (slightly), methanol (slightly, sonicated), water (slightly)
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -42℃ for long term (months to years).
MSDS:
Inquire
Melting Point:
>208°C (dec.)
InChIKey:
RTCIKUMODPANKX-JBUOLDKXSA-M
InChI:
1S/C7H11N3O6S.Na/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15;/h4-5H,1-3H2,(H2,8,11)(H,13,14,15);/q;+1/p-1/t4-,5+;/m1./s1
Canonical SMILES:
O=C1N(OS(=O)(O[Na])=O)[C@H]2CN1[C@H](C(N)=O)CC2
Current Developer:
Allergan; AstraZeneca; Cerexa; Novexel; Pfizer
1.Inactivation of TEM-1 by avibactam (NXL-104): insights from quantum mechanics/molecular mechanics metadynamics simulations.
Sgrignani J;Grazioso G;De Amici M;Colombo G Biochemistry. 2014 Aug 12;53(31):5174-85. doi: 10.1021/bi500589x. Epub 2014 Jul 30.
The fast and constant development of drug-resistant bacteria represents a serious medical emergence. To overcome this problem, the development of drugs with new structures and modes of action is urgently needed. In this context, avibactam represents a promising, innovative inhibitor of beta-lactamases with a novel molecular structure compared to previously developed inhibitors, showing a promising inhibitory activity toward a significant number of beta-lactamase enzymes. In this work, we studied, at the atomistic level, the mechanisms of formation of the covalent complex between avibactam and TEM-1, an experimentally well-characterized class A beta-lactamase, using classical and quantum mechanics/molecular mechanics (QM/MM) simulations combined with metadynamics. Our simulations provide a detailed structural and energetic picture of the molecular steps leading to the formation of the avibactam/TEM-1 covalent adduct. In particular, they support a mechanism in which the rate-determining step is the water-assisted Glu166 deprotonation by Ser70. In this mechanistic framework, the predicted activation energy is in good agreement with experimental kinetic measurements. Additionally, our simulations highlight the important role of Lys73 in assisting the Ser70 and Ser130 deprotonations.
2.Novel beta-lactam antibiotics and inhibitor combinations.
Bassetti M;Righi E;Viscoli C Expert Opin Investig Drugs. 2008 Mar;17(3):285-96. doi: 10.1517/13543784.17.3.285 .
BACKGROUND: ;beta-Lactam antibiotics are the most used antibacterial agents in clinical practice, but the development of resistance poses some questions about their future leading to an urgent requirement for new compounds. Specifically, beta-lactamases represent the commonest single cause of bacterial resistance to beta-lactam antibiotics. Numerous chromosomal and plasmid-mediated types are known and classified on the basis of their structure. Among them, extended-spectrum beta-lactamases (ESBLs) and AmpC beta-lactamase can confer broad-spectrum antibiotic resistance to ureidopenicillins, third-generation cephalosporins and aztreonam, posing unique therapeutic challenges. Furthermore, the spreading emergence of carbapenemases is a significant threat to the management of nosocomial infections.;OBJECTIVE: ;To review characteristics of new drugs for beta-lactam resistance.;METHODS: ;We reviewed the principal characteristics of the new drugs studied for overcoming the emergence of beta-lactam resistance among Gram-negative and Gram-positive pathogens.;RESULTS/CONCLUSIONS: ;We included in our review new beta-lactamase inhibitors (Ro 48-1220), non-beta-lactam compounds (NXL-104), new oxapenenems (AM-112, -113, -114, -115) and penems (faropenem), new cephalosporins (ceftobiprole and ceftaroline) and new carbapenems (doripenem).
3.Beta-lactams and beta-lactamase-inhibitors in current- or potential-clinical practice: a comprehensive update.
Shahid M;Sobia F;Singh A;Malik A;Khan HM;Jonas D;Hawkey PM Crit Rev Microbiol. 2009;35(2):81-108. doi: 10.1080/10408410902733979.
The use of successive generations of beta-lactams has selected successive generations of beta-lactamases including CTX-M ESBLs, AmpC beta-lactamases, and KPC carbapenamases in Enterobacteriaceae. Moreover, this cephalosporin resistance, along with rising resistance to fluoroquinolones, is now driving the use of carbapenems and unfortunately the carbapenem resistance has emerged markedly, especially in Acinetobacter spp. due to OXA- and metallo-carbapenemases. The industry responded to the challenge of rising resistance and recently developed some novel beta-lactams such as ceftobiprole, ceftaroline etc. and many beta-lactam compounds, including beta-lactamase-inhibitors, such as BMS-247243, S-3578, RWJ-54428, CS-023, SMP-601, NXL 104, BAL 30376, LK 157, and so on are under trials. This review provides the comprehensive accounts of the developments in penicillins, cephalosporins, carbapenems, and beta-lactamase-inhibitors, and the insight about medicinal chemistry, mechanism(s) of action and resistance, potential strategies to overcome resistance due to beta-lactamases, and also the recent advancements in the development of newer beta-lactam compounds; some of which are still under trials and yet to be classified.
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CAS 1192491-61-4 Avibactam Sodium Salt

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