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Avibactam sodium

Avibactam sodium structure

CAS No:
1192491-61-4
Formula:
C7H11N3O6S.Na
Chemical Name:
Avibactam sodium
Synonyms:
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
Categories:
Active Pharmaceutical Ingredients > Inhibitor Drugs

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.

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.

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-).

Avibactam sodium Basic Attributes

Molecular Weight：

288.23

Color/Form：

White to Off-White

Characteristics

Melting Point：

>208°C (dec.)

Water Solubility：

H2O: 2mg/mL, clear

Critical Temperature & Pressure：

Sealed in dry,Room Temperature

Safety Information

wgk germany：

WGK 3

Avibactam sodium Use and Manufacturing

Avibactam (NXL104) is a novel β-lactamase inhibitor with a non-lactam structural scaffold. NXL104 irreversibly inhibits lactamase from Mycobacterium tuberculosis.

Drug Function and Efficacy

It is a non-β-lactam β-lactamase inhibitor that works by forming a covalent adduct with the enzyme that is not easily hydrolyzed. It can inhibit Ambler class A and C β-lactamases and some class D β-lactamases, including extended-spectrum β-lactamases (ESBLs), KPC and OXA-48 carbapenemases, and AmpC enzymes. It does not inhibit class B enzymes (metallo-β-lactamases) and cannot inhibit many class D enzymes.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ceftazidime Avibactam Sodium for Injection
Ingredients	This product is a compound preparation, whose components are ceftazidime pentahydrate (equivalent to ceftazidime C22H22N6O7S22.0g) and avibactam sodium (equivalent to avibactam C7H11N3O6S0.5g). Ceftazidime pentahydrate Chemical name: (6R,7R)-7-[[(2-amino-4-thiazolyl)-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-methylpyridinium inner salt pentahydrate Molecular formula: C22H32N6O12S2 Molecular weight: 636.7 Avibactam sodium Chemical name: [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]-octane-6-yl] sodium sulfate Molecular formula: C7H10N3O6SNa Molecular weight: 287.23 Excipients: anhydrous sodium carbonate.
Indication	In vitro, avibactam has no significant inhibitory effect on cytochrome P450 enzymes. Avibactam and ceftazidime at clinically relevant concentrations did not induce cytochrome P450 in vitro. Avibactam and ceftazidime do not inhibit major renal or hepatic transporters within the clinically relevant exposure range, and interactions that may occur through these mechanisms are therefore considered minimal. In vitro, avibactam at clinically relevant concentrations in human liver microsomes did not inhibit cytochrome P450 isoenzymes CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4/5. Avibactam had no ability to induce CYP1A2/2B6/2C9 and 3A4 in human hepatocytes in vitro. Avibactam had a slight ability to induce CYP2E1 at very high concentrations that exceeded clinically relevant exposures. Ceftazidime was evaluated alone in human hepatocytes and showed no ability to induce the activity or mRNA expression of CYP1A1/2, CYP2B6, and CYP3A4/5. Neither ceftazidime nor avibactam at clinically relevant concentrations is an inhibitor of the following hepatic or renal transporters: MDR1, BCRP, OAT1, OAT3, OATP1B1, OATP1B3, BSEP, MRP4, OCT1, and OCT2. Based on results in human embryonic kidney cells expressing these transporters, avibactam is not a substrate for MDR1, BCRP, MRP4, or OCT2, but is a substrate for the human OAT1 and OAT3 renal transporters. In vitro, probenecid inhibited the uptake of avibactam by 56-70% through inhibition of OAT1 and OAT3. Ceftazidime does not inhibit OAT1- and OAT3-mediated transport of avibactam. The clinical impact of potent OAT inhibitors on the pharmacokinetics of avibactam is unknown. It is not recommended to use this product and probenecid at the same time. Human clinical trials have confirmed that there is no interaction between ceftazidime and avibactam, and there is no interaction between ceftazidime/avibactam and metronidazole. The administration of ceftazidime may cause false positive reactions for glucose in the urine of certain test methods. It is recommended to use glucose oxidase-mediated enzymatic reactions to detect glucose. Other forms of interaction The combined use of high doses of cephalosporins and nephrotoxic drugs, such as aminoglycosides or potent diuretics (such as furosemide), may have adverse effects on renal function (see [Precautions]). In vitro, chloramphenicol antagonizes ceftazidime and other cephalosporins. The clinical relevance of this result is unknown, but due to the possible antagonism in vivo, combined use should be avoided.
Specifications	2.5g (22.0g C22H22N6O7 flakes and 0.5g C7H11N3O6 flakes)

Registered Holders

Reyoung Pharmaceutical Co., Ltd.

China
Active
Nanjing Libowei Pharmaceutical Co., Ltd.

China
Active
Guangxi Kelun Pharmaceutical Co., Ltd.

China
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