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    Avibactam

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    2D Structure
    Also known as: 1192500-31-4, Avibactam free acid, Nxl104, Ave-1330a free acid, Avibactam (free acid), Nxl-104 free acid
    Molecular Formula
    C7H11N3O6S
    Molecular Weight
    265.25  g/mol
    InChI Key
    NDCUAPJVLWFHHB-UHNVWZDZSA-N
    FDA UNII
    06MFO7817I
    Avibactam is a non--lactam -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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
    2.1.2 InChI
    InChI=1S/C7H11N3O6S/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+/m1/s1
    2.1.3 InChI Key
    NDCUAPJVLWFHHB-UHNVWZDZSA-N
    2.1.4 Canonical SMILES
    C1CC(N2CC1N(C2=O)OS(=O)(=O)O)C(=O)N
    2.1.5 Isomeric SMILES
    C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    06MFO7817I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Nxl 104

    2. Nxl-104

    3. Nxl104

    2.3.2 Depositor-Supplied Synonyms

    1. 1192500-31-4

    2. Avibactam Free Acid

    3. Nxl104

    4. Ave-1330a Free Acid

    5. Avibactam (free Acid)

    6. Nxl-104 Free Acid

    7. Chembl1689063

    8. Chebi:85984

    9. 06mfo7817i

    10. [(2s,5r)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] Hydrogen Sulfate

    11. 396731-14-9

    12. (2s,5r)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

    13. 1,6-diazabicyclo(3.2.1)octane-2-carboxamide, 7-oxo-6-(sulfooxy)-, (1r,2s,5r)-rel-

    14. (1r,2s,5r)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl Hydrogen Sulfate

    15. Avibactam [inn]

    16. Avibactam [usan:inn]

    17. Unii-06mfo7817i

    18. Avibactamfreeacid

    19. Sulfuric Acid, Mono((1r,2s,5r)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo(3.2.1)oct-6-yl) Ester

    20. Sulfuric Acid, Mono[(1r,2s,5r)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester

    21. Unii-7352665165

    22. Avibactam [mi]

    23. Avibactam [usan]

    24. Avibactam [who-dd]

    25. Schembl1666807

    26. Avibactam, (+/-)-

    27. Gtpl10761

    28. Dtxsid901026066

    29. Amy24028

    30. Avi

    31. Zavicefta Component Avibactam

    32. Zinc9302239

    33. Bdbm50339145

    34. Avibactam Component Of Zavicefta

    35. Cs-0593

    36. Db09060

    37. Ac-35749

    38. Hy-14879

    39. E80372

    40. Q15410251

    41. Trans-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octan-2-carboxamide

    42. (1r,2s,5r)-7-oxo-6-sulfooxy-1,6-diazabicyclo(3.2.1)octane-2-carboxamide

    43. 794508-22-8

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 265.25 g/mol
    Molecular Formula C7H11N3O6S
    XLogP3-1.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass265.03685625 g/mol
    Monoisotopic Mass265.03685625 g/mol
    Topological Polar Surface Area139 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity457
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 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

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    beta-Lactamase Inhibitors

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

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    AVIBACTAM
    5.2.2 FDA UNII
    7352665165
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - beta Lactamase Inhibitors
    5.3 Absorption, Distribution and Excretion

    Route of Elimination

    Avibactam and ceftazidime are excreted mainly by the kidneys.

    Volume of Distribution

    The steady state volumes of distribution of avibactam and ceftazidime is 22.2L and 17L respectively.

    Clearance

    Avibactam and ceftazidime has a clearance of ~12L/h and ~7L/h respectively.

    5.4 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 .

    5.5 Biological Half-Life

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

    5.6 Mechanism of Action

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