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Avibactam

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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

Avibactam

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 Formula	C₇H₁₁N₃O₆S
Molecular Weight	265.25 g/mol
XLogP3	-1.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	265.03685625 g/mol
Monoisotopic Mass	265.03685625 g/mol
Topological Polar Surface Area	139 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	457
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

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.