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    Sisomicin

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: Rickamicin, Sisomycin, 32385-11-8, Sissomicin, Antibiotic 6640, Antibiotic 66-40
    Molecular Formula
    C19H37N5O7
    Molecular Weight
    447.5  g/mol
    InChI Key
    URWAJWIAIPFPJE-YFMIWBNJSA-N
    FDA UNII
    X55XSL74YQ
    Antibiotic produced by Micromonospora inyoensis. It is closely related to gentamicin C1A, one of the components of the gentamicin complex (GENTAMICINS).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
    2.1.2 InChI
    InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
    2.1.3 InChI Key
    URWAJWIAIPFPJE-YFMIWBNJSA-N
    2.1.4 Canonical SMILES
    CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O
    2.1.5 Isomeric SMILES
    C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    X55XSL74YQ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,5 Dehydrogentamicin

    2. 4,5-dehydrogentamicin

    3. Antibiotic 6640

    4. Extramycin

    5. Pathomycin

    6. Rickamicin

    7. Sch 13475

    8. Sch-13475

    9. Sch13475

    10. Siseptin

    11. Sisomicin Sulfate

    12. Sisomicin Sulfate (2:5) Salt

    13. Sisomycin

    14. Sissomicin

    15. Sizomycin

    2.3.2 Depositor-Supplied Synonyms

    1. Rickamicin

    2. Sisomycin

    3. 32385-11-8

    4. Sissomicin

    5. Antibiotic 6640

    6. Antibiotic 66-40

    7. Sch 13475

    8. Dehydrogentamicin Cla

    9. Sch-13475

    10. X55xsl74yq

    11. Chebi:9169

    12. Sisomin

    13. D-streptamine, O-3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-

    14. Sisomicinum

    15. Sisomicina

    16. Sisomicine

    17. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

    18. Sisomicine [inn-french]

    19. Sisomicinum [inn-latin]

    20. Salvamina

    21. Sisomicina [inn-spanish]

    22. Siseptin Sulfate

    23. (1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranoside

    24. (1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranoside

    25. (2r,3r,4r,5r)-2-(((1s,2s,3r,4s,6r)-4,6-diamino-3-(((2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2h-pyran-3,5-diol

    26. O-2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy-d-streptamine

    27. Einecs 251-018-2

    28. Unii-x55xsl74yq

    29. Brn 1357913

    30. Sisomicin [usan:inn:ban]

    31. Sch13475

    32. Sisomicin-sulfate

    33. Sis

    34. Siso

    35. Sisomicin [inn]

    36. Sisomicin [mi]

    37. Sisomicin (usan/inn)

    38. Sisomicin [usan]

    39. Sisomicin [who-dd]

    40. Schembl49395

    41. O-2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6)-2-deoxy-d-streptamine

    42. O-3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-l-streptamine

    43. Chembl221886

    44. Gtpl10858

    45. (2s-cis)-4-o-(3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)-2-deoxy-6-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl)-d-streptamine

    46. Zinc56870809

    47. Akos015895179

    48. Db12604

    49. (2s-cis)-4-o-(3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl)-2-deoxy-6-o-(3-deoxy-4-c-methyl-3-(methylamino)-beta-l-arabinopyranosyl)-d-streptamine

    50. 85s118

    51. C00494

    52. D02544

    53. Gentamicin Sulfate Impurity A [ep Impurity]

    54. Q3962119

    55. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol

    56. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

    57. 2-deoxy-4-o-(3-deoxy-4-c-methyl-3-(methylamino)-.beta.-l-arabinopyranosyl)-6-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-glycero-hex-4-enopyranosyl)-l-streptamine

    58. O-3-deoxy-4-c-methyl-3-(methylamino)-.beta-l-arabinopyranosyl-(1->4)-o-(2,6-diamino-2,3,4,6-tetradeoxy-.alpha.-d-glycero-hex-4-enopyranosyl-(1->6))-2-deoxy-l-streptamine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 447.5 g/mol
    Molecular Formula C19H37N5O7
    XLogP3-5.1
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count6
    Exact Mass447.26929854 g/mol
    Monoisotopic Mass447.26929854 g/mol
    Topological Polar Surface Area214 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity643
    Isotope Atom Count0
    Defined Atom Stereocenter Count11
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Protein Synthesis Inhibitors

    Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

    Anti-Bacterial Agents

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

    4.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01G - Aminoglycoside antibacterials

    J01GB - Other aminoglycosides

    J01GB08 - Sisomicin