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2D Structure
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

An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.
1 2D Structure

2D Structure

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