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    Nebicina

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    2D Structure
    Also known as: 49842-07-1, Tobramycin sulphate, Nebcin, Tobramycinsulfate, 79645-27-5, Mls000069826
    Molecular Formula
    C18H39N5O13S
    Molecular Weight
    565.6  g/mol
    InChI Key
    ZEUUPKVZFKBXPW-TWDWGCDDSA-N
    An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid
    2.1.2 InChI
    InChI=1S/C18H37N5O9.H2O4S/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1
    2.1.3 InChI Key
    ZEUUPKVZFKBXPW-TWDWGCDDSA-N
    2.1.4 Canonical SMILES
    C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N.OS(=O)(=O)O
    2.1.5 Isomeric SMILES
    C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N.OS(=O)(=O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Brulamycin

    2. Nebcin

    3. Nebicin

    4. Nebramycin Factor 6

    5. Obracin

    6. Sulfate, Tobramycin

    7. Tobracin

    8. Tobramycin

    2.2.2 Depositor-Supplied Synonyms

    1. 49842-07-1

    2. Tobramycin Sulphate

    3. Nebcin

    4. Tobramycinsulfate

    5. 79645-27-5

    6. Mls000069826

    7. Smr000058891

    8. Dartobcin

    9. Nebcine

    10. Tobraneg

    11. Tobrasix

    12. (2s,3r,4s,5s,6r)-4-amino-2-{[(1s,2s,3r,4s,6r)-4,6-diamino-3-{[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol Sulfate

    13. Opera_id_1050

    14. Schembl2837

    15. Chembl1200780

    16. Hms2230j04

    17. Mfcd00133864

    18. Akos025310614

    19. 842t071

    20. A923784

    21. Tobramycin Sulfate Salt, Aminoglycoside Antibiotic

    22. Q-201838

    23. 2-ethoxy-5-[(morpholine-4-carbonyl)-amino]-benzenesulfonylchloride

    24. (2s,3r,4s,5s,6r)-4-amino-2-(((1s,2s,3r,4s,6r)-4,6-diamino-3-(((2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2h-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,5-diol Sulfate

    25. (2s,3r,4s,5s,6r)-4-amino-2-((1s,2s,3r,4s,6r)-4,6-diamino-3-((2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2h-pyran-2-yloxy)-2-hydroxycyclohexyloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,5-diol Sulfate

    26. (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol,sulfuric Acid

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 565.6 g/mol
    Molecular Formula C18H39N5O13S
    Hydrogen Bond Donor Count12
    Hydrogen Bond Acceptor Count18
    Rotatable Bond Count6
    Exact Mass565.22650749 g/mol
    Monoisotopic Mass565.22650749 g/mol
    Topological Polar Surface Area351 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity691
    Isotope Atom Count0
    Defined Atom Stereocenter Count14
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 3  
    Drug NameTOBRAMYCIN SULFATE
    Active IngredientTOBRAMYCIN SULFATE
    CompanyAKORN (Application Number: A205179); BAXTER HLTHCARE CORP (Application Number: A206965); FRESENIUS KABI USA (Application Number: A065122); FRESENIUS KABI USA (Application Number: N050789); HOSPIRA (Application Number: A063111); HOSPIRA (Application Number: A063112); MYLAN LABS LTD (Application Number: A065407); TEVA PHARMS USA (Application Number: A063100); WEST-WARD PHARMS INT (Application Number: A063117); X GEN PHARMS (Application Number: A065013); XELLIA PHARMS APS (Application Number: A205685)

    2 of 3  
    Drug NameTOBRAMYCIN SULFATE (PHARMACY BULK)
    Active IngredientTOBRAMYCIN SULFATE
    CompanyFRESENIUS KABI USA (Application Number: A065120)

    3 of 3  
    Drug NameTOBRAMYCIN SULFATE IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER
    Active IngredientTOBRAMYCIN SULFATE
    CompanyHOSPIRA (Application Number: A063081)

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Aminoglycosides [CS]; Aminoglycoside Antibacterial [EPC]