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Chemistry

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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

Relebactam

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 Formula	C₁₂H₂₀N₄O₆S
Molecular Weight	348.38 g/mol
XLogP3	-3.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	348.11035554 g/mol
Monoisotopic Mass	348.11035554 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	585
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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