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    Also known as: 119413-54-6, Topotecan hcl, Hycamtin, Nogitecan hydrochloride, Topotecan (hydrochloride), Topotecan monohydrochloride
    Molecular Formula
    C23H24ClN3O5
    Molecular Weight
    457.9  g/mol
    InChI Key
    DGHHQBMTXTWTJV-BQAIUKQQSA-N
    FDA UNII
    956S425ZCY
    Topotecan Hydrochloride
    An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.
    1 2D Structure

    Topotecan Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;hydrochloride
    2.1.2 InChI
    InChI=1S/C23H23N3O5.ClH/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20;/h5-8,27,30H,4,9-11H2,1-3H3;1H/t23-;/m0./s1
    2.1.3 InChI Key
    DGHHQBMTXTWTJV-BQAIUKQQSA-N
    2.1.4 Canonical SMILES
    CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O.Cl
    2.1.5 Isomeric SMILES
    CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    956S425ZCY
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 9 Dimethylaminomethyl 10 Hydroxycamptothecin

    2. 9-dimethylaminomethyl-10-hydroxycamptothecin

    3. Hycamtamine

    4. Hycamtin

    5. Hydrochloride, Nogitecan

    6. Hydrochloride, Topotecan

    7. Nogitecan Hydrochloride

    8. Nsc 609699

    9. Nsc-609699

    10. Nsc609699

    11. Sk And F 104864 A

    12. Sk And F-104864-a

    13. Sk And F104864a

    14. Skf 104864 A

    15. Skf-104864-a

    16. Skf104864a

    17. Topotecan

    18. Topotecan Monohydrochloride, (s)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 119413-54-6

    2. Topotecan Hcl

    3. Hycamtin

    4. Nogitecan Hydrochloride

    5. Topotecan (hydrochloride)

    6. Topotecan Monohydrochloride

    7. Sk&f S-104864-a

    8. Evotopin

    9. Topotecan Hydrochloride [usan]

    10. Nsc 609699

    11. Topotecan Teva

    12. Topotecan Actavis

    13. Topotecan Hospira

    14. Nsc609699

    15. Skf 104864a

    16. Nsc-609699

    17. Nsc-759263

    18. Topotecan (as Hydrochloride)

    19. (s)-10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione Monohydrochloride

    20. 956s425zcy

    21. Sk&f-s-104864-a

    22. Ncgc00095189-01

    23. Hycamtin (tn)

    24. Skf 104864a; Nsc 609669

    25. Dsstox_cid_25952

    26. Dsstox_rid_81248

    27. Dsstox_gsid_45952

    28. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-, Monohydrochloride, (s)-

    29. Nogitecan Hydrochloride (jan)

    30. Topotecan Hydrochloride (usan)

    31. Skf 104864a (hydrochloride);nsc 609669 (hydrochloride)

    32. Topotecanhydrochloride

    33. Chembl1607

    34. Hycamptamine Hydrochloride

    35. Nogitecan Hydrochloride [jan]

    36. (s)-10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione Hydrochloride

    37. Smr000466344

    38. Cas-119413-54-6

    39. Sk&f-s-104864a

    40. Nsc 609669

    41. Drg-0288

    42. 9-dimethylaminomethyl-10-hydroxycamptothecin.

    43. Potactasol

    44. Evotropin

    45. Unii-956s425zcy

    46. Nogitecan Hcl

    47. Potactasol (tn)

    48. (s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione Hydrochloride

    49. Topotecan Hydrocholoride

    50. Topotecan Hcl - Hycamtin

    51. Schembl7247

    52. Hycamtin (tn) (glaxosmith)

    53. Mls000759456

    54. Mls001401447

    55. Spectrum1505820

    56. Dtxsid1045952

    57. Skfs 104864a

    58. Hms1922h22

    59. Pharmakon1600-01505820

    60. 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione Hydrochloride

    61. Amy24931

    62. Bcp00930

    63. Skf-104864a

    64. Skf-s 104864-a

    65. Topotecan Hydrochloride [mi]

    66. Tox21_111478

    67. Ccg-37460

    68. Hy-13768a

    69. Mfcd00866235

    70. Ncgc00014925

    71. Nci609699

    72. Nk-211

    73. Nsc759263

    74. S1231

    75. Akos015900415

    76. Sk&f 104864-a

    77. Tox21_111478_1

    78. Ac-1551

    79. Cs-1498

    80. Ks-1410

    81. Nc00177

    82. Nsc 759263

    83. Topotecan Hydrochloride [mart.]

    84. Topotecan Hydrochloride [vandf]

    85. Topotecan Hydrochloride [usp-rs]

    86. Topotecan Hydrochloride [who-dd]

    87. Ncgc00014925-06

    88. Ncgc00095189-02

    89. Ncgc00095189-03

    90. Sw197557-5

    91. T-160

    92. T2795

    93. Topotecan Hydrochloride [orange Book]

    94. D02168

    95. 413t546

    96. E-89/001

    97. 9-dimethylaminomethyl-10-hydroxycamptothecin, Hcl Salt

    98. Q27271753

    99. 9-[(dimethylamino)methyl]-10-hydroxy-(20s)-camptothecin, Hcl

    100. (4s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4',6-7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

    101. (4s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dionehydrochloride (1:1)

    102. (s)-10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dionehydrochloride

    103. (s)-10-((dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1h-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione Hydrochloride

    104. (s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dionemonohydrochloride

    105. (s)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[l,2-b]quinoline-3,14(4h,12h)-dione Monohydrochloride

    106. 1h-pyrano[3',7]indolizino[1,2-b]quinoline- 3,14(4h,12h)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, Monohydrochloride, (4s)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 457.9 g/mol
    Molecular Formula C23H24ClN3O5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass457.1404486 g/mol
    Monoisotopic Mass457.1404486 g/mol
    Topological Polar Surface Area103 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity867
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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 2  
    Drug NameTopotecan hydrochloride
    Drug LabelTopotecan hydrochloride is a semi-synthetic derivative of camptothecin and is an anti-tumor drug with topoisomerase I-inhibitory activity.The chemical name for topotecan hydrochloride is (S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[...
    Active IngredientTopotecan hydrochloride
    Dosage FormInjectable; Solution
    RouteInjection; Intravenous
    Strengtheq 4mg base/4ml (eq 1mg base/ml); eq 4mg base/vial
    Market StatusPrescription
    CompanyHospira; Fresenius Kabi Oncol; Accord Hlthcare; Sun Pharm Inds; Innopharma Licensing; Teva Pharms Usa; Actavis Elizabeth; Fresenius Kabi Usa; Onco Therapies; Sagent Pharms; Dr Reddys Labs; Three Rivers Pharms

    2 of 2  
    Drug NameTopotecan hydrochloride
    Drug LabelTopotecan hydrochloride is a semi-synthetic derivative of camptothecin and is an anti-tumor drug with topoisomerase I-inhibitory activity.The chemical name for topotecan hydrochloride is (S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[...
    Active IngredientTopotecan hydrochloride
    Dosage FormInjectable; Solution
    RouteInjection; Intravenous
    Strengtheq 4mg base/4ml (eq 1mg base/ml); eq 4mg base/vial
    Market StatusPrescription
    CompanyHospira; Fresenius Kabi Oncol; Accord Hlthcare; Sun Pharm Inds; Innopharma Licensing; Teva Pharms Usa; Actavis Elizabeth; Fresenius Kabi Usa; Onco Therapies; Sagent Pharms; Dr Reddys Labs; Three Rivers Pharms

    4.2 Drug Indication

    Hycamtin capsules are indicated as monotherapy for the treatment of adult patients with relapsed small cell lung cancer (SCLC) for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan is indicated for the treatment of patients with metastatic carcinoma of the ovary after failure of first-line or subsequent therapy.

    Hycamtin capsules are indicated as monotherapy for the treatment of adult patients with relapsed small cell lung cancer (SCLC) for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan monotherapy is indicated for the treatment of patients with relapsed small-cell lung cancer (SCLC) for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan in combination with cisplatin is indicated for patients with carcinoma of the cervix recurrent after radiotherapy and for patients with stage IVB disease. Patients with prior exposure to cisplatin require a sustained treatment-free interval to justify treatment with the combination.

    Topotecan monotherapy is indicated for the treatment of patients with relapsed small cell lung cancer [SCLC] for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan in combination with cisplatin is indicated for patients with carcinoma of the cervix recurrent after radiotherapy and for patients with Stage IVB disease. Patients with prior exposure to cisplatin require a sustained treatment free interval to justify treatment with the combination.

    Topotecan monotherapy is indicated for the treatment of:

    - patients with metastatic carcinoma of the ovary after failure of first-line or subsequent therapy

    - patients with relapsed small cell lung cancer (SCLC) for whom re-treatment with thefirst-line regimen is not considered appropriate.

    Topotecan in combination with cisplatin is indicated for patients with carcinoma of the cervix recurrent after radiotherapy and for patients with Stage IVB disease. Patients with prior exposure to cisplatin require a sustained treatment free interval to justify treatment with the combination.

    Topotecan monotherapy is indicated for the treatment of:

    - patients with metastatic carcinoma of the ovary after failure of first line or subsequent therapy;

    - patients with relapsed small cell lung cancer [SCLC] for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan in combination with cisplatin is indicated for patients with carcinoma of the cervix recurrent after radiotherapy and for patients with Stage IVB disease. Patients with prior exposure to cisplatin require a sustained treatment free interval to justify treatment with the combination.

    Topotecan monotherapy is indicated for the treatment of patients with relapsed small cell lung cancer (SCLC) for whom re-treatment with the first-line regimen is not considered appropriate.

    Topotecan in combination with cisplatin is indicated for patients with carcinoma of the cervix recurrent after radiotherapy and for patients with Stage IVB disease. Patients with prior exposure to cisplatin require a sustained treatment free interval to justify treatment with the combination.

    Topotecan is indicated for the treatment of patients with metastatic carcinoma of the ovary after failure of first-line or subsequent therapy.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Topoisomerase I Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Topoisomerase Inhibitors [MoA]; Topoisomerase Inhibitor [EPC]
    5.3 ATC Code

    L01CE01

    L01XX17

    L01XX17

    L01XX17

    L01XX17

    L01XX17

    L01XX17

    API Reference Price

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    14-Jul-2021
    18-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - SOLUTION;INTRAVENOUS - EQ 1MG BASE/M...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1MG BASE/ML (EQ 1MG BASE/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 200199

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    DOSAGE - SOLUTION;INTRAVENOUS - EQ 3MG BASE/3...DOSAGE - SOLUTION;INTRAVENOUS - EQ 3MG BASE/3ML (EQ 1MG BASE/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 200199

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    DOSAGE - SOLUTION;INTRAVENOUS - EQ 4MG BASE/4...DOSAGE - SOLUTION;INTRAVENOUS - EQ 4MG BASE/4ML (EQ 1MG BASE/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 200199

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    DOSAGE - SOLUTION;INTRAVENOUS - EQ 4MG BASE/4...DOSAGE - SOLUTION;INTRAVENOUS - EQ 4MG BASE/4ML (EQ 1MG BASE/ML)

    USFDA APPLICATION NUMBER - 200582

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    DOSAGE - INJECTABLE;INJECTION - EQ 4MG BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 4MG BASE/VIAL

    USFDA APPLICATION NUMBER - 20671

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    DOSAGE - CAPSULE;ORAL - EQ 0.25MG BASE

    USFDA APPLICATION NUMBER - 20981

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    DOSAGE - CAPSULE;ORAL - EQ 1MG BASE

    USFDA APPLICATION NUMBER - 20981

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