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    Relebactam

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 1174018-99-5, Mk-7655, Relebactam anhydrous, Relebactam [inn], (-)-relebactam anhydrous, 1oqf7tt3pf
    Molecular Formula
    C12H20N4O6S
    Molecular Weight
    348.38  g/mol
    InChI Key
    SMOBCLHAZXOKDQ-ZJUUUORDSA-N
    FDA UNII
    1OQF7TT3PF
    Relebactam is a diazabicyclooctane beta-lactamase inhibitor, similar in structure to [avibactam]. It includes a piperidine ring which reduces export from bacterial cells by producing a positive charge. It is currently available in a combination product which includes [imipenem] and [cilastatin] to treat complicated urinary tract infections (UTIs), pyelonephritis, and complicated intra-abdominal infections in adults. It is considered to be a last-line treatment option and gained FDA approval as part of the combination product Recarbrio in July 2019.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,5R)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
    2.1.2 InChI
    InChI=1S/C12H20N4O6S/c17-11(14-8-3-5-13-6-4-8)10-2-1-9-7-15(10)12(18)16(9)22-23(19,20)21/h8-10,13H,1-7H2,(H,14,17)(H,19,20,21)/t9-,10+/m1/s1
    2.1.3 InChI Key
    SMOBCLHAZXOKDQ-ZJUUUORDSA-N
    2.1.4 Canonical SMILES
    C1CC(N2CC1N(C2=O)OS(=O)(=O)O)C(=O)NC3CCNCC3
    2.1.5 Isomeric SMILES
    C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)NC3CCNCC3
    2.2 Other Identifiers
    2.2.1 UNII
    1OQF7TT3PF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s,5r)-7-oxo-n-(4-piperidinyl)-6-(sulfooxy)-1,6-diazabicyclo(3.2.1)octane-2-carboxamide

    2. Mk-7655

    3. Mk7655

    4. Relebactam Anhydrous

    2.3.2 Depositor-Supplied Synonyms

    1. 1174018-99-5

    2. Mk-7655

    3. Relebactam Anhydrous

    4. Relebactam [inn]

    5. (-)-relebactam Anhydrous

    6. 1oqf7tt3pf

    7. Chembl3112741

    8. Mk-7655a

    9. Mk7655

    10. Sulfuric Acid Mono-((2s,5r)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diaza-bicyclo(3.2.1)oct-6-yl) Ester

    11. (1r,2s,5r)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl Hydrogen Sulfate

    12. [(2s,5r)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] Hydrogen Sulfate

    13. Unii-1oqf7tt3pf

    14. Relebactam [mi]

    15. Relebactam [who-dd]

    16. Bdbm1858

    17. Schembl3721178

    18. Gtpl10852

    19. Ex-a864

    20. Sulfuric Acid Mono-[7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diaza-bicyclo[3.2.1]oct-6-yl] Ester

    21. Bdbm50447651

    22. Mfcd28502833

    23. Zinc43206319

    24. Cs-5391

    25. Db12377

    26. Ac-36163

    27. As-35205

    28. Br163749

    29. Hy-16752

    30. Us8487073, 1a

    31. S0074

    32. J3.628.086g

    33. Mk-7655;mk7655;mk 7655

    34. J-690043

    35. Q27252695

    36. (2s,5r)-7-oxo-n-piperidin-4-yl-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

    2.4 Create Date
    2009-08-03
    3 Chemical and Physical Properties
    Molecular Weight 348.38 g/mol
    Molecular Formula C12H20N4O6S
    XLogP3-3.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass348.11035554 g/mol
    Monoisotopic Mass348.11035554 g/mol
    Topological Polar Surface Area137 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity585
    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

    Relebactam is indicated in combination with [imipenem] and [cilastatin] for the treatment of complicated urinary tract infections (including pyelonephritis), and complicated intra-abdominal infections caused by susceptible organisms in adults.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Relebactam prevents the hydrolysis of [imipenem], allowing it to exert its bactericidal effect.

    5.2 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.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    Currently, relebactam is only available as an intravenous product; therefore, there is no relevant absorption data in the literature.

    Route of Elimination

    Approximately 90-100% of relebactam is renally eliminated.

    Volume of Distribution

    Relebactam has a volume of distribution of approximately 19 L with both single and steady state dosing.

    Clearance

    Relebactam has a reported total clearance of approximately 130-150 mL/min (8 L/h). About 30% of the total drug clearance can be attributed to active tubular secretion.

    5.4 Metabolism/Metabolites

    Relebactam does not undergo significant metabolism and can be found mostly unchanged in human plasma.

    5.5 Biological Half-Life

    Relebactam has a half-life of 1.2 hours as per official FDA labeling. Values reported in pharmacokinetic studies vary from 1.35-1.8 hours.

    5.6 Mechanism of Action

    Relebactam is a beta-lactamase inhibitor known to inhibit many types of beta-lactamases including Ambler class A and Ambler class C enzymes, helping to prevent [imipenem] from degrading in the body. Similar to the structurally-related [avibactam], first, relebactam binds non-covalently to a beta-lactamase binding site, then, it covalently acylates the serine residue in the active site of the enzyme. In contrast to some other beta-lactamase inhibitors, once relebactam de-acylates from the active site, it can reform it's 5 membered ring and is capable of rebinding to target enzymes.