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    Technical details about Arbekacin, learn more about the structure, uses, toxicity, action, side effects and more

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    Arbekacin

    APIs // Active Pharmaceutical Ingredients

    PRICE INFORMATION

    MARKET PLACE

    DIGITAL CONTENT

    PharmaCompass

    Biophore is a research-driven global pharmaceutical company focused on niche APIs for the generic industry.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    1. 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

    2D Structure

    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 Weight 552.6 g/mol
    Molecular Formula C22H44N6O10
    XLogP3-6.8
    Hydrogen Bond Donor Count11
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count10
    Exact Mass552.31189162 g/mol
    Monoisotopic Mass552.31189162 g/mol
    Topological Polar Surface Area297 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity757
    Isotope Atom Count0
    Defined Atom Stereocenter Count14
    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

    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.

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