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Avibactam

Avibactam structure

CAS No:
1192500-31-4
Formula:
C7H11N3O6S
Chemical Name:
Avibactam
Synonyms:
Sulfuric acid,mono[(1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester;Avibactam
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Avibactam free acid is a covalent, reversible β-lactamase inhibitor, inhibits β-lactamase TEM-1 and CTX-M-15 with IC50 of 8 nM and 5 nM, respectively.

Avibactam is a member of the class of azabicycloalkanes that is (2S,5R)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide in which the amino hydrogen at position 6 is replaced by a sulfooxy group. Used (in the form of its sodium salt) in combination with ceftazidime pentahydrate for the treatment of complicated urinary tract infections including pyelonephritis. It has a role as an antibacterial drug, an antimicrobial agent and an EC 3.5.2.6 (beta-lactamase) inhibitor. It is a monocarboxylic acid amide, a member of ureas, an azabicycloalkane and a hydroxylamine O-sulfonic acid. It is a conjugate acid of an avibactam(1-).|Avibactam is a non-β-lactam β-lactamase inhibitor that is available in combination with ceftazidime (Avycaz). This combination was approved by the FDA on February 25, 2015 for the treatment of complicated intra-abdominal infections in combination with metronidazole, and the treatment of complicated urinary tract infections, including pyelonephritis caused by antibiotic resistant-pathogens, including those caused by multi-drug resistant gram-negative bacterial pathogens. As there is limited clinical safety and efficacy data, Avycaz should be reserved for patients over 18 years old who have limited or not alternative treatment options.|Avibactam is a beta Lactamase Inhibitor. The mechanism of action of avibactam is as a beta Lactamase Inhibitor.

Avibactam Basic Attributes

Molecular Weight：

265.25 g/mol

Exact Mass：

265.24

UNII：

7352665165

Characteristics

PSA：

139.61000

XLogP3：

-3.20

Density：

1.9±0.1 g/cm3

Refractive Index：

1.679

Toxicity

Toxicity Summary：

Avycaz is contraindicated in patients with known serious hypersensitivity to avibactam-containing products, ceftazidime or other members of the cephalosporin class.

Protein Binding：

5.7%-8.2% of avibactam is bound to plasma protein, and less than 10% of ceftazidime is protein bound.

Drug Information

Drug Indication：

AVYCAZ (ceftazidime-avibactam), in combination with metronidazole, is indicated for the treatment of complicated intra-abdominal infections caused by the following susceptible microorganisms: Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Providencia stuartii, Enterobacter cloacae, Klebsiella oxytoca, and Pseudomonas aeruginosa in patients 18 years or older. AVYCAZ is also indicated for the treatment of complicated urinary tract infections including pyelonephritis caused by the following susceptible microorganisms: Escherichia coli, Klebsiella pneumoniae, Citrobacter koseri, Enterobacter aerogenes, Enterobacter cloacae, Citrobacter freundii, Proteus spp., and Pseudomonas aeruginosa in patients 18 years or older.|FDA Label|Treatment of infections caused by aerobic gram-negative bacteria|Treatment of Gram-negative bacterial infections, Treatment of intra-abdominal infections, Treatment of pneumonia, Treatment of urinary tract infections

MeSH：

Endogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES. (See all compounds classified as beta-Lactamase Inhibitors.)

Absorption：

Avibactam and ceftazidime are excreted mainly by the kidneys.|The steady state volumes of distribution of avibactam and ceftazidime is 22.2L and 17L respectively.|Avibactam and ceftazidime has a clearance of ~12L/h and ~7L/h respectively.

Metabolism/Metabolites：

No metabolism of avibactam was observed in human liver preparations. Unchanged avibactam is the major drug-related component in human plasma and urine. 80-90% of ceftazidime is eliminated as unchanged .

Biological Half-Life：

Ceftazidime-avibactam has a half life of ~2.7-3.0 hours.

Mechanism of Action：

Avibactam is a non-β lactam β-lactamase inhibitor that inactivates some β-lactamases (Ambler class A β-lactamases, including Klebsiella pneumoniae carbapenemases, Ambler class C and some Ambler class D β-lactamases) by a unique covalent and reversible mechanism, and protects ceftazidime from degradation by certain β-lactamases. Avibactam rapidly reaches the periplasm of bacteria at high enough concentrations to restore activity of ceftazidime against ceftazidime-resistant, β-lactamase-producing strains. Avibactam does not decrease the activity of ceftazidime against ceftazidime susceptible organisms.

MeSH Entry Terms：

avibactam

Avibactam Use and Manufacturing

Uses

Avibactam intermediate

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:265.25
XLogP3:-1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:265.03685625
Monoisotopic Mass:265.03685625
Topological Polar Surface Area:139
Heavy Atom Count:17
Complexity:457
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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