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    Berubicin Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    PharmaCompass
    $ API Ref.Price (USD/KG) : 511,450Xls

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    2D Structure
    Also known as: Berubicin hcl, Wp744, Berubicin hydrochloride [usan], Rta 744, Wp-744, 293736-67-1
    Molecular Formula
    C34H36ClNO11
    Molecular Weight
    670.1  g/mol
    InChI Key
    GPMIHHFZKBVWAZ-LMMKTYIZSA-N
    FDA UNII
    7BA3X03948
    Berubicin Hydrochloride is the hydrochloride salt of the anthracycline derivative berubicin with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, and RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
    2.1.2 InChI
    InChI=1S/C34H35NO11.ClH/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40;/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3;1H/t16-,20-,22-,24-,33+,34-;/m0./s1
    2.1.3 InChI Key
    GPMIHHFZKBVWAZ-LMMKTYIZSA-N
    2.1.4 Canonical SMILES
    CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OCC6=CC=CC=C6.Cl
    2.1.5 Isomeric SMILES
    C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OCC6=CC=CC=C6.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    7BA3X03948
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Rta744

    2. Wp 744

    3. Wp-744

    4. Wp744 Cpd

    2.3.2 Depositor-Supplied Synonyms

    1. Berubicin Hcl

    2. Wp744

    3. Berubicin Hydrochloride [usan]

    4. Rta 744

    5. Wp-744

    6. 293736-67-1

    7. Rta-744

    8. 7ba3x03948

    9. Berubicin Hydrochloride (usan)

    10. Unii-7ba3x03948

    11. Wp 744

    12. Chembl2103796

    13. Dtxsid10951913

    14. Berubicin Hydrochloride [who-dd]

    15. 293736-67-1 (hcl)

    16. D08871

    17. Q27268015

    18. (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

    19. (8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

    20. (8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

    21. (8s,10s)-10-((3-amino-4-o-benzyl-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)- 6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene- 5,12-dione Hydrochloride

    22. 3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-4-o-benzyl-2,3,6-trideoxyhexopyranoside--hydrogen Chloride (1/1)

    23. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8s,10s)-, Hydrochloride

    24. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s,10s)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 670.1 g/mol
    Molecular Formula C34H36ClNO11
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass669.1976887 g/mol
    Monoisotopic Mass669.1976887 g/mol
    Topological Polar Surface Area195 Ų
    Heavy Atom Count47
    Formal Charge0
    Complexity1130
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in brain cancer.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    RTA 744 is a substance being studied in the treatment of adult brain tumors. RTA 744 crosses the blood-brain barrier and blocks an enzyme needed for cancer growth. RTA 744 is a type of topoisomerase inhibitor. Also called topoisomerase II inhibitor RTA 744.