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    Also known as: Therarubicin (tn), Pirarubicin hydrochloride, Pinorubin (tn), Dtxsid00915024, D08386, (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-[(2s)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride
    Molecular Formula
    C32H38ClNO12
    Molecular Weight
    664.1  g/mol
    InChI Key
    ZPHYPKKFSHAVOE-QXTSSQDCSA-N
    Pirarubicin HCl
    Pirarubicin Hydrochloride is the hydrochloride salt form of pirarubicin, an analogue of the anthracycline antineoplastic antibiotic doxorubicin with antineoplastic activity. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair as well as RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.
    1 2D Structure

    Pirarubicin HCl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-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/C32H37NO12.ClH/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38;/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3;1H/t14-,17-,19-,21-,22-,31+,32-;/m0./s1
    2.1.3 InChI Key
    ZPHYPKKFSHAVOE-QXTSSQDCSA-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)OC6CCCCO6.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)O[C@H]6CCCCO6.Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 4'-o-tetrahydropyranyladriamycin

    2. 4'-o-tetrahydropyranyldoxorubicin

    3. 4'-o-tetrapyranyldoxorubicin

    4. Pirarubicin

    5. Pirarubicin Hydrochloride

    6. Thprubicine

    7. Thepirubicin

    8. Theprubicin

    9. Therarubicin

    10. Thp-adm

    11. Thp-adriamycin

    12. Thp-dox

    13. Thp-doxorubicin

    2.2.2 Depositor-Supplied Synonyms

    1. Therarubicin (tn)

    2. Pirarubicin Hydrochloride

    3. Pinorubin (tn)

    4. Dtxsid00915024

    5. D08386

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

    7. 3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-o-oxan-2-ylhexopyranoside--hydrogen Chloride (1/1)

    2.3 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 664.1 g/mol
    Molecular Formula C32H38ClNO12
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count7
    Exact Mass663.2082533 g/mol
    Monoisotopic Mass663.2082533 g/mol
    Topological Polar Surface Area204 Ų
    Heavy Atom Count46
    Formal Charge0
    Complexity1120
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

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