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Arbekacin

Synopsis, Chemistry

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Also known as: 51025-85-5, Arbekacina, Haberacin, Arbekacine, Arbekacinum, Arbekacin [inn]

Molecular Formula

C₂₂H₄₄N₆O₁₀

Molecular Weight

552.6 g/mol

InChI Key

MKKYBZZTJQGVCD-XTCKQBCOSA-N

FDA UNII

G7V6SLI20L

Arbekacin is a semisynthetic aminoglycoside antibiotic derived from dibekacin with activity against both gram-positive and gram-negative bacteria. Arbekacin is most commonly used in the treatment of multi-resistant bacterial infections.

1 2D Structure

Arbekacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide

2.1.2 InChI

InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1

2.1.3 InChI Key

MKKYBZZTJQGVCD-XTCKQBCOSA-N

2.1.4 Canonical SMILES

C1CC(C(OC1CN)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CO)O)N)O)NC(=O)C(CCN)O)N)N

2.1.5 Isomeric SMILES

C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)NC(=O)[C@H](CCN)O)N)N

2.2 Other Identifiers

2.2.1 UNII

G7V6SLI20L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-n-((s)-4-amino-2-hydroxybutyryl)dibekacin

2. 4-amino-2-hydroxybutylyldibekacin

3. Arbekacin Sulfate

4. Habekacin

5. Me1100

2.3.2 Depositor-Supplied Synonyms

1. 51025-85-5

2. Arbekacina

3. Haberacin

4. Arbekacine

5. Arbekacinum

6. Arbekacin [inn]

7. Me1100

8. G7v6sli20l

9. Chebi:37922

10. Arbekacin (inn)

11. 51025-85-5 (free Base)

12. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-4-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide

13. Me-1100

14. Arbekacine [french]

15. Arbekacinum [latin]

16. Arbekacin Sulfate [jan]

17. Arbekacina [spanish]

18. Npc-14

19. (s)-4-amino-n-((1r,2s,3s,4r,5s)-5-amino-2-(((2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-4-(((2r,3r,6s)-3-amino-6-(aminomethyl)tetrahydro-2h-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide

20. Ncgc00167530-01

21. Unii-g7v6sli20l

22. Dkb-ahb

23. Arbekacin [mi]

24. Arbekacin [who-dd]

25. Schembl18413

26. Chembl426926

27. Gtpl7345

28. Dtxsid8048319

29. Zinc9575047

30. Akos025149466

31. Db06696

32. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1-4))-n(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (s)-

33. D-streptamine, O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1-4))-n1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (s)-

34. O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1->4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1->6))-n'-((2s)-4-amino-2-hydroxybutyryl)-2-deoxy-l-streptamine

35. O-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1-6))-n'-((2s)-4-amino-2-hydroxybutyryl)-2-deoxy-l-streptamine

36. D07462

37. 025a855

38. Q4784668

39. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-2-(3-amino-3-deoxy-alpha-d-glucopyranosyloxy)-4-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide

40. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-2-{[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide

41. (2s)-4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-4-[(2r,3r,6s)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-2-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide

42. (2s)-4-amino-n-{(1r,2s,3s,4r,5s)-5-amino-2-[(3-amino-3-deoxy-alpha-d-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide

43. (s)-4-amino-n-((1r,2s,3s,4r,5s)-5-amino-2-((2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-4-((2r,3r,6s)-3-amino-6-(aminomethyl)tetrahydro-2h-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide

44. 84g

45. Butanamide, 4-amino-n-[(1r,2s,3s,4r,5s)-5-amino-2-[(3-amino-3-deoxy-.alpha.-d-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-erythro-hexopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2s)-

46. D-streptamine, O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-erythro-hexopyranosyl-(1->4))-n1-((2s)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-

47. O-3-amino-3-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-erythro-hexopyranosyl-(1->6))-n'-((2s)-4-amino-2-hydroxybutyryl)-2-deoxy-l-streptamine

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₄₄N₆O₁₀
Molecular Weight	552.6 g/mol
XLogP3	-6.8
Hydrogen Bond Donor Count	11
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	10
Exact Mass	552.31189162 g/mol
Monoisotopic Mass	552.31189162 g/mol
Topological Polar Surface Area	297 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	757
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
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

Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Arbekacin is an aminoglycoside. Aminoglycosides function by binding to bacterial 30S ribosomal subunits, causing t-RNA misreads, and preventing the production of proteins. Anaerobes are less susceptible to aminoglycosides because they do not spend as much energy as aerobes on taking up chemicals like aminoglycosides. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01G - Aminoglycoside antibacterials

J01GB - Other aminoglycosides

J01GB12 - Arbekacin

5.4 Absorption, Distribution and Excretion

Absorption

Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.

5.5 Biological Half-Life

3 hours

5.6 Mechanism of Action

Arbekacin irreversibly binds bacterial 30S and 16S ribosomal subunits inhibiting protein synthesis. Arbekacin binds to 4 nucleotides of the 16S subunit and 1 amino acid of protein S12 to interfere with the decoding site around nucleotide 1400 in the 16S subunit. Interference with the decoding site interferes with its interaction with the wobble base of tRNA. This hindered interaction causes mRNA to be misread and the incorrect amino acids are inserted into protein. These error filled proteins are not able to function or may even be toxic.