ChemicalBook > CAS DataBase List > Avibactam sodium

Avibactam sodium

Avibactam sodium Structure
Avibactam sodium
  • CAS No.1192491-61-4
  • Chemical Name:Avibactam sodium
  • CBNumber:CB72621657
  • Molecular Formula:C7H12N3NaO6S
  • Formula Weight:289.24
  • MOL File:1192491-61-4.mol
Avibactam sodium Property
  • Melting point >208°C (dec.)
  • storage temp. Sealed in dry,Room Temperature
  • solubility DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly, Sonicated)
  • form Solid
  • color White to Off-White
  • Water Solubility H2O: 2mg/mL, clear
  • InChI InChI=1/C7H11N3O6S.Na.H/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);;/t4-,5+;;/s3
  • InChIKey JKMUNBAKQJMVKG-NLZGLQCHNA-N
  • SMILES C([C@@H]1CC[C@H]2N(OS(O)(=O)=O)C(=O)[N@@]1C2)(=O)N.[NaH] |&1:1,4,13,r|
  • FDA UNII 9V824P8TAI
  • UNSPSC Code 51101500
  • NACRES NA.21
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H319-H315-H335
  • Precautionary statements P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Avibactam sodium Chemical Properties,Usage,Production

  • Description Avibactam sodium (NXL-104), a diazabicyclooctanone compound, is currently the most favoured novel β-lactamase inhibitor. Compared with the three marketed β-lactamase inhibitors, NXL-104 has a long duration of action and reversible covalent binding to the enzyme, and does not induce β-lactamase production.
  • Characteristics Avibactam sodium is a novel beta-lactamase inhibitor. In its structure, Na+ readily forms coordination bonds with water molecules. In addition, there are several O atoms as hydrogen bond acceptors and -NH2 as hydrogen bond donors. As a result, avibactam sodium crystallises easily into its hydrated form[1]. The structure is shown below:
    Molecular structure of Avibactam sodium
  • History Avibactam sodium and its free acid, avibactam, are diazabicyclooctane (DBO)–based, non-β-lactam β-lactamase inhibitors (BLIs) that are used to treat multi-drug–resistant Gram-negative bacterial pathogens. The compounds were jointly developed by Actavis Generics (now part of Teva Pharmaceutical Industries) and AstraZeneca.
    In 2015, avibactam sodium, in combination with ceftazidime, a cephalosporin antibiotic, was approved by the US Food and Drug Administration. The dual-drug’s target was complex urinary tract and intra-abdominal infections caused by Gram-negative, often hospital-acquired, bacteria.
    In 2018, in the continuing quest to combat multi-drug–resistant bacteria, Eric M. Gordon, Matthew A. J. Duncton, and Mark A. Gallop at Arixa Pharmaceuticals (Palo Alto, CA) prepared analogues of avibactam that are more orally available than the free acid or its salt.
  • Uses Avibactam (NXL104) is a novel β-lactamase inhibitor with a non-lactam structural scaffold. NXL104 irreversibly inhibits lactamase from Mycobacterium tuberculosis.
  • Definition ChEBI: Avibactam sodium is an organic sodium salt that is the monosodium salt of avibactam. Used in combination with ceftazidime pentahydrate for the treatment of complicated urinary tract infections including pyelonephritis. It has a role as an EC 3.5.2.6 (beta-lactamase) inhibitor, an antibacterial drug and an antimicrobial agent. It contains an avibactam(1-).
  • Biological Activity Avibactam[1192491-61-4] is a β-lactamase inhibitor (IC50s = 8, 80, and 38 nM for TEM-1, P99, and KPC-2 β-lactamases, respectively). It restores the antimicrobial activity of ceftazidime , ceftriaxone , imipenem , and piperacillin against antibiotic-resistant Enterobacteriaceae in vitro (MIC90 reduction 4-1,024-fold across 190 E. coli and K. pneumoniae clinical isolates). Formulations containing avibactam have been used to treat carbapenem-resistant Enterobacteriaceae infections.
  • Synthesis A solution of sodium 2-ethyl hexanoate (475.0 g, 2.850 mol) in ethanol (2.00 L) was added to a solution of tetrabutylammonium [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] sulfate 13 (723.0 g) in ethanol (2.50 l) and water (50 mL) over approximately 1 h, and the temperature was maintained at rt. The reaction mixture was held for 2 h. The product was filtered, washed with ethanol (2 × 2.0 L), and dried to yield a white crystalline solid 1 (395.0 g, 96.2%), mp 259.1–262.4 °C (decomposition); [α]D20 = ?46.40 (c = 0.79, MeOH/H2O = 1/1); 1H NMR (500 MHz, D2O) δ 4.15 (dd, J = 5.8, 2.8 Hz, 1H), 4.01 (d, J = 7.5 Hz, 1H), 3.28 (d, J = 12.2 Hz, 1H), 3.06 (d, J = 12.2 Hz, 1H), 2.23–2.09 (m, 1H), 2.06–1.96 (m, 1H), 1.94–1.82 (m, 1H), 1.81–1.69 (m, 1H). 13C NMR (126 MHz, D2O) δ 174.72 (s), 169.53 (s), 60.43 (s), 59.93 (s), 47.33 (s), 20.03 (s), 18.31 (s). IR (cm–1): 3459, 1749, 1675, 1361, 1270, 1013, 857, 768. MS (ESI) m/z: 279.0 [M + H]+.
    synthesis of avibactam sodium
  • IC 50 CTX-M-15: 5 nM; TEM-1: 8 nM
  • References [1] STACHYRATHéRèSE. Mechanistic studies of the inactivation of TEM-1 and P99 by NXL104, a novel non-beta-lactam beta-lactamase inhibitor.[J]. Antimicrobial Agents and Chemotherapy, 2010: 5132-5138. DOI:10.1128/AAC.00568-10.
    [2] BONNEFOYALAIN. In vitro activity of AVE1330A, an innovative broad-spectrum non-beta-lactam beta-lactamase inhibitor.[J]. Journal of Antimicrobial Chemotherapy, 2004, 54 2: 410-417. DOI:10.1093/jac/dkh358.
    [3] LAGACé-WIENSP R S. Activity of NXL104 in combination with beta-lactams against genetically characterized Escherichia coli and Klebsiella pneumoniae isolates producing class A extended-spectrum beta-lactamases and class C beta-lactamases.[J]. Antimicrobial Agents and Chemotherapy, 2011, 55 5: 2434-2437. DOI:10.1128/AAC.01722-10.
    [4] KINGMADELINE. Multicenter Study of Outcomes with Ceftazidime-Avibactam in Patients with Carbapenem-Resistant Enterobacteriaceae Infections.[J]. Antimicrobial Agents and Chemotherapy, 2017, 61 7. DOI:10.1128/AAC.00449-17.
    [5] ZHIYONG DING. Understanding the Role of Water in Different Solid Forms of Avibactam Sodium and Its Affecting Mechanism[J]. Crystal Growth & Design, 2020, 20 2: 1150-1161. DOI:10.1021/acs.cgd.9b01459.
    [6] TAO WANG. A New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation[J]. Organic Process Research & Development, 2017, 22 3: 267-272. DOI:10.1021/acs.oprd.7b00290.
Avibactam sodium Preparation Products And Raw materials
Raw materials
Preparation Products
Avibactam sodium Suppliers
Global(344)Suppliers
  • Supplier：
    S&Y Biochem Co.,Ltd
  • Tel： +8617774091612
  • Email：marketing@sybiochem.com
  • Country：China
  • ProdList：179
  • Advantage：58
  • Supplier：
    airuikechemical co., ltd.
  • Tel：+86-18353166132<br/>+86-18353166132
  • Email：sales02@airuikechemical.com
  • Country：China
  • ProdList：983
  • Advantage：58
  • Supplier：
    Capot Chemical Co.,Ltd.
  • Tel：+86-（0）57185586718<br/>+86-13336195806
  • Email：sales@capot.com
  • Country：China
  • ProdList：29730
  • Advantage：60
Avibactam sodium Spectrum
1192491-61-4, Avibactam sodiumRelated Search:
  • Amines, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
  • Sulfur & Selenium Compounds
  • Pharmaceuticals
  • Intermediates & Fine Chemicals
  • Chiral Reagents
  • Amines
  • API
  • β内酰胺酶抑制剂
  • 抗生素
  • 医药化学试剂
  • 药靶配体
  • 大化工产品
  • 实验室
  • 医药原料药API
  • API医药原料
  • 原料
  • 试剂
  • 抗感染类
  • 化学试剂
  • 化学原料药
  • 医用原料
  • 杂质对照品
  • 中间体
  • 医用原料
  • 抑制剂
  • 对照品-杂质对照品
  • 医药原料
  • 抗菌药物
  • 原料药
  • 医药标准品
  • 医药原料药
  • C7H10N3O6SNa
  • C7H10N3NaO6S
  • 阿维巴坦钠,10 MM DMSO 溶液
  • 阿维巴坦纳对照品
  • 优选]AVIBACTAM SODIUM
  • PERFEMIKER]咪唑并[1,2-A]吡啶-7-醇
  • 阿维巴坦纳
  • 阿维巴坦钠 NXL 104 AVIBACTAMSODIUM
  • (2S,5R)-1,6-二氮杂环[3.2.1]辛烷-2-甲酰胺-7-氧代-6-(磺酸基)-钠盐
  • 阿维巴坦钠盐
  • 阿维巴坦、阿维巴坦钠
  • (1R,2S,5R)-2-氨甲酰基-7-氧代-1,6-二氮杂双环[3.2.1]辛烷-6-基硫酸钠盐
  • 关环甲酰胺硫酸盐
  • 阿维巴坦标准品-NA
  • 阿维巴坦杂质30
  • 硫酸单[(1R,2S,5R)-2-(氨基羰基)-7-氧代-1,6-氮杂双环[3.2.1]辛-6-基]酯钠盐
  • AVIBACTAMSODIUMSALT\N阿维巴坦钠
  • 阿米巴坦钠盐
  • 阿维巴坦
  • 阿维巴坦中间体4
  • 阿维巴坦钠
  • 阿维巴坦杂质 1
  • 1192491-61-4
  • Avibactam sodium, 10 mM in DMSO
  • Avibactum Sodium
  • Sodium Avibactam
  • Avibatan

Home

My