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    Epirubicin Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    $ API Ref.Price (USD/KG) : 106,524Xls

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    2D Structure
    Also known as: Pharmorubicin, 56390-09-1, Ellence, Epirubicin hcl, Farmorubicin, Farmorubicina
    Molecular Formula
    C27H30ClNO11
    Molecular Weight
    580.0  g/mol
    InChI Key
    MWWSFMDVAYGXBV-FGBSZODSSA-N
    FDA UNII
    22966TX7J5
    An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-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/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22-,27-;/m0./s1
    2.1.3 InChI Key
    MWWSFMDVAYGXBV-FGBSZODSSA-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)O.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.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    22966TX7J5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4' Epi Adriamycin

    2. 4' Epi Doxorubicin

    3. 4' Epi Dxr

    4. 4' Epiadriamycin

    5. 4' Epidoxorubicin

    6. 4'-epi-adriamycin

    7. 4'-epi-doxorubicin

    8. 4'-epi-dxr

    9. 4'-epiadriamycin

    10. 4'-epidoxorubicin

    11. Ellence

    12. Epi Cell

    13. Epi-cell

    14. Epicell

    15. Epilem

    16. Epirubicin

    17. Farmorubicin

    18. Farmorubicina

    19. Farmorubicine

    20. Hydrochloride, Epirubicin

    21. Imi 28

    22. Imi-28

    23. Imi28

    24. Nsc 256942

    25. Nsc-256942

    26. Nsc256942

    27. Pharmorubicin

    2.3.2 Depositor-Supplied Synonyms

    1. Pharmorubicin

    2. 56390-09-1

    3. Ellence

    4. Epirubicin Hcl

    5. Farmorubicin

    6. Farmorubicina

    7. Imi-28

    8. 4'-epidoxorubicin Hydrochloride

    9. Epirubicin Ebewe

    10. Epirubicin (hydrochloride)

    11. Nsc-759195

    12. Mls001401404

    13. Nsc 256942

    14. Pidorubicin

    15. Wp-697

    16. 22966tx7j5

    17. 4'-epi-adriamycin Hydrochloride

    18. Smr000466308

    19. 56390-09-1 (hcl)

    20. (8s,10s)-10-(((2r,4s,5r,6s)-4-amino-5-hydroxy-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

    21. Epirubitec

    22. 4'-epi-adriamycin

    23. Epidoxorubicin Hydrochloride

    24. (7s,9s)-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

    25. Ccris 4477

    26. Einecs 260-145-2

    27. Unii-22966tx7j5

    28. Ellence (tn)

    29. 4'-epi-doxorubicin

    30. Epirubicin Hydrochlorid

    31. 4'-epidoxorubicin Hcl

    32. Cpd000466308

    33. Epirubicin Hydrochloride [usan:usp:jan]

    34. E-adm

    35. 4'-epi-dx

    36. Schembl3165

    37. (1s,3s)-3-glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranoside Hydrochloride

    38. Mls000759412

    39. 4-epidoxorubicin Hydrochloride

    40. Epirubicin Hcl [vandf]

    41. Chembl1200981

    42. Dtxsid50860297

    43. Pharmakon1600-01505708

    44. Amy10308

    45. Ex-a2654

    46. Epirubicin Hcl (4'-epidoxorubicin)

    47. Epirubicin Hydrochloride [mi]

    48. Hy-13624a

    49. Mfcd00941448

    50. Nsc759195

    51. S1223

    52. Epirubicin Hydrochloride (jp17/usp)

    53. Epirubicin Hydrochloride [jan]

    54. Bcp9000651

    55. Ccg-100950

    56. Cs-1773

    57. Epirubicin Hydrochloride [usan]

    58. Nc00200

    59. Epirubicin Hydrochloride [mart.]

    60. Epirubicin Hydrochloride [usp-rs]

    61. Epirubicin Hydrochloride [who-dd]

    62. (8s-cis)-10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione Hydrochloride

    63. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s-cis)-

    64. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-arabinohexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s,10s)-

    65. As-75323

    66. Epirubicin Hydrochloride, >=90% (hplc)

    67. E0840

    68. Epirubicin Hydrochloride [orange Book]

    69. D02214

    70. D83113

    71. Epirubicin Hydrochloride [ep Monograph]

    72. Epirubicin Hydrochloride [usp Monograph]

    73. Sr-01000763557

    74. Q-101406

    75. Sr-01000763557-3

    76. Q27253634

    77. Epirubicin Hydrochloride, British Pharmacopoeia (bp) Reference Standard

    78. Epirubicin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    79. Epirubicin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    80. (1s,3s)-3-glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-.alpha.-l-arabino-hexopyranoside Hydrochloride

    81. (8s,10s)-10-(((2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dionehydrochloride

    82. (8s,10s)-10-((2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

    83. (8s,10s)-10-{[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione Hydrochloride

    84. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s-cis)-

    85. 5,12-naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, Hydrochloride (1:1), (8s,10s)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 580.0 g/mol
    Molecular Formula C27H30ClNO11
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count5
    Exact Mass579.1507385 g/mol
    Monoisotopic Mass579.1507385 g/mol
    Topological Polar Surface Area206 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity977
    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 Information
    1 of 4  
    Drug NameEllence
    Drug LabelELLENCE Injection (epirubicin hydrochloride injection) is an anthracycline cytotoxic agent, intended for intravenous administration. ELLENCE is supplied as a sterile, clear, red solution and is available in polypropylene vials containing 50 and 200 m...
    Active IngredientEpirubicin hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml)
    Market StatusPrescription
    CompanyPfizer

    2 of 4  
    Drug NameEpirubicin hydrochloride
    Drug LabelEpirubicin hydrochloride injection is an anthracycline cytotoxic agent, intended for intravenous administration. Epirubicin hydrochloride injection is supplied as a sterile, clear, red solution and is available invials containing 50 mg and 200 mg o...
    Active IngredientEpirubicin hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml); 150mg/75ml (2mg/ml); 10mg/5ml (2mg/ml)
    Market StatusPrescription
    CompanyActavis Elizabeth; Fresenius Kabi Usa; Hospira; Fresenius Kabi Oncol; Ebewe Pharma; Onco Therapies; Teva Pharms Usa; Eurohlth Intl; Cipla; Hisun Pharm Hangzhou; Akorn

    3 of 4  
    Drug NameEllence
    Drug LabelELLENCE Injection (epirubicin hydrochloride injection) is an anthracycline cytotoxic agent, intended for intravenous administration. ELLENCE is supplied as a sterile, clear, red solution and is available in polypropylene vials containing 50 and 200 m...
    Active IngredientEpirubicin hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml)
    Market StatusPrescription
    CompanyPfizer

    4 of 4  
    Drug NameEpirubicin hydrochloride
    Drug LabelEpirubicin hydrochloride injection is an anthracycline cytotoxic agent, intended for intravenous administration. Epirubicin hydrochloride injection is supplied as a sterile, clear, red solution and is available invials containing 50 mg and 200 mg o...
    Active IngredientEpirubicin hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml); 150mg/75ml (2mg/ml); 10mg/5ml (2mg/ml)
    Market StatusPrescription
    CompanyActavis Elizabeth; Fresenius Kabi Usa; Hospira; Fresenius Kabi Oncol; Ebewe Pharma; Onco Therapies; Teva Pharms Usa; Eurohlth Intl; Cipla; Hisun Pharm Hangzhou; Akorn

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antibiotics, Antineoplastic

    Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

    Topoisomerase II Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Anthracyclines [CS]; Topoisomerase Inhibitors [MoA]; Anthracycline Topoisomerase Inhibitor [EPC]