Avibactam sodium

Product Name: Avibactam sodium
CAS No.: 1192491-61-4
Chemical Name: Avibactam sodium
Synonyms: Avibactam (sodium);AvibactaM SodiuM Salt;Sulfuric Acid Mono[(1R,2S,5R)-2-(aMinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester SodiuM Salt;134760;NXL 104;Avabatan;Avibatan;AVE-1330A;Avibactam-001-Na;Avidabate sodium
CBNumber: CB72621657
Molecular Formula: C7H12N3NaO6S
Formula Weight: 289.24
MOL File: 1192491-61-4.mol

More

Less

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
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|

More

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

More

Less

N-Bromosuccinimide Price

Cayman Chemical

Product number: 22825
Product name: Avibactam (sodium salt)
Purity: ≥95%
Packaging: 1mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 22825
Product name: Avibactam (sodium salt)
Purity: ≥95%
Packaging: 5mg
Price: $356
Updated: 2024/03/01

Cayman Chemical

Product number: 22825
Product name: Avibactam (sodium salt)
Purity: ≥95%
Packaging: 10mg
Price: $632
Updated: 2024/03/01

Cayman Chemical

Product number: 22825
Product name: Avibactam (sodium salt)
Purity: ≥95%
Packaging: 25mg
Price: $1184
Updated: 2024/03/01

TRC

Product number: A794850
Product name: AvibactamSodiumSalt
Packaging: 1mg
Price: $60
Updated: 2021/12/16

More

Less

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:

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]+.

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

More

Less

Avibactam sodium Suppliers

Canada 1 China 311 China Hong Kong 1 India 8 United States 12 Global 333

Wuhan Jingkangen Biomedical Technology Co., Ltd

Tel: 13720134139 13720134139
Email: orders@jknbiochem.com
Country: China
ProdList: 5821
Advantage: 58

Hubei Chuangliankangcheng Pharmaceutical Co., Ltd.

Tel: 027-65388397 18164111589
Fax: 027-65388397
Email: 3321478047@qq.com
Country: China
ProdList: 1996
Advantage: 55

Chengdu Climb Pharmaceutical Technology Co., Ltd.

Tel: 028-87608726 13540107218
Fax: 028-87608725
Email: sales@cdclimb.com
Country: China
ProdList: 104
Advantage: 58

Zhuhai Yourun Co., Ltd.

Tel: 0756-6811852 13923369215
Fax: 0756-6811857
Email: zhuhaiyourun@126.com
Country: China
ProdList: 235
Advantage: 55

Shanghai Mixiu Chemical Co., Ltd.

Tel: 18101936766
Fax: 021-58583907
Email: eileen@shmychem.com
Country: China
ProdList: 350
Advantage: 55

Jinan Xinzheng Pharmaceutical Technology Co., Ltd.

Tel: 0531-88798968 18615218958
Email: yin3684895@126.com
Country: China
ProdList: 174
Advantage: 58

Enantiotech Corporation Ltd

Tel: 760-85282375 13212762451
Email: marketing@enantiotech.net
Country: China
ProdList: 153
Advantage: 55

Dezhou Honghai Pharmaceutical Technology Co., Ltd

Tel: +86-15552645780 +86-17658510842
Email: 17658510842@163.com
Country: China
ProdList: 13
Advantage: 58

Shandong Risen-Sun Pharmaceutical Co., Ltd

Tel: +8615621883869 15621883869
Email: liutf@jewim.com.cn
Country: China
ProdList: 108
Advantage: 58

Shanghai Boyle Chemical Co., Ltd.

Tel
Fax: 86-21-57758967
Email: sales@boylechem.com
Country: China
ProdList: 2922
Advantage: 55

More

Less

View Lastest Price from Avibactam sodium manufacturers

Cangzhou Kangrui Pharma Tech Co. Ltd.,

Product: Avibactam sodium 1192491-61-4
Price: US $0.00-0.00/g
Min. Order: 50g
Purity: 99%
Supply Ability: 10kgs
Release date: 2024-10-18

hebei hongtan Biotechnology Co., Ltd

Product: Avibactam sodium 1192491-61-4
Price: US $90.00/kg
Min. Order: 1kg
Purity: 99.9%
Supply Ability: 1000
Release date: 2024-03-21

S&Y Biochem Co.,Ltd

Product: Avibactam Sodium Salt 1192491-61-4
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99
Supply Ability: 200
Release date: 2024-08-01

1192491-61-4, Avibactam sodiumRelated Search:

(2S,5R)-ethyl 5-(benzyloxyaMino)piperidine-2-carboxylate Avibactam Impurity 15 trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid Carbamic acid, [2-(aminooxy)ethyl]-, 1,1-dimethylethyl ester (9CI) Avibactam Impurity 3(2R,5S) Avibactam Sodium Isomer methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate tert-butyl (S)-2-((aminooxy)methyl)pyrrolidine-1-carboxylate Avibactam Impurity 10 AvibactaM Avibactam (sodium hydrate) Avibactam Impurity 7 (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide Avibactam Impurity 25 Avibactam impurity 23 Avibactam INT 1 Avibactam Impurity 12 Avibactam Impurity 28

AvibactaM SodiuM Salt

NXL 104

Sulfuric Acid Mono[(1R,2S,5R)-2-(aMinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester SodiuM Salt

Avibactam (sodium)

AvibactaM SodiuM NXL 104

sodium (1R,2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate

(2S,5R)-7-Oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide monosodium salt

(2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt

AvibactaM SodiuM Sal

SODIUM;[(2S,5R)-2-CARBAMOYL-7-OXO-1,6-DIAZABICYCLO[3.2.1]OCTAN-6-YL] SULFATE

Avabatan

NXL-104;NXL 104;NXL104

Avibactam-001-Na

NXL 104, Sulfuric Acid Mono[(1R,2S,5R)-2-(aMinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester SodiuM Salt

134760

Sulfuric acid, mono[(1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester, sodium salt (1:1)

Sulfuric Acid Mono[(1R,2S,5R)-2-(aMinocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester SodiuM Salt(Avibactam Sodium Salt)

AVE-1330A

Avidabate sodium

5,7-diethyl-2-(3-nitrophenyl)-1,3-diazaadamantan-10-one

Benzenesulfonylchloride,5-chloro-2-methoxy-9-methyl-

Avibatan

Sodium Avibactam

Avibactum Sodium

1192491-61-4

C7H10N3NaO6S

C7H10N3O6SNa

API

Amines

Chiral Reagents

Intermediates & Fine Chemicals

Pharmaceuticals

Sulfur & Selenium Compounds

Amines, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds