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Chemistry

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Also known as: Idarubicin hcl, 57852-57-0, Idamycin, Zavedos, Idarubicin (hydrochloride), 4-demethoxydaunorubicin
Molecular Formula
C26H28ClNO9
Molecular Weight
534.0  g/mol
InChI Key
JVHPTYWUBOQMBP-RVFAQHLVSA-N
FDA UNII
5VV3MDU5IE

Idarubicin Hydrochloride
An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.
1 2D Structure

Idarubicin Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
2.1.2 InChI
InChI=1S/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15-,16-,17-,21+,26-;/m0./s1
2.1.3 InChI Key
JVHPTYWUBOQMBP-RVFAQHLVSA-N
2.1.4 Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)C)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=CC=CC=C5C4=O)O)(C(=O)C)O)N)O.Cl
2.2 Other Identifiers
2.2.1 UNII
5VV3MDU5IE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4 Demethoxydaunorubicin

2. 4 Desmethoxydaunorubicin

3. 4-demethoxydaunorubicin

4. 4-desmethoxydaunorubicin

5. Hydrochloride, Idarubicin

6. Idarubicin

7. Imi 30

8. Imi-30

9. Imi30

10. Nsc 256439

11. Nsc-256439

12. Nsc256439

2.3.2 Depositor-Supplied Synonyms

1. Idarubicin Hcl

2. 57852-57-0

3. Idamycin

4. Zavedos

5. Idarubicin (hydrochloride)

6. 4-demethoxydaunorubicin

7. Imi 30

8. Imi-30

9. 5vv3mdu5ie

10. Idarubicinhydrochloride

11. Cpd000466355

12. 4-demethoxydaunorubicin Hydrochloride

13. Mls001401448

14. Nsc-256439

15. Dsstox_cid_27775

16. Dsstox_rid_82550

17. Dsstox_gsid_47797

18. Smr000466355

19. Idamycin Pfs

20. Cas-57852-57-0

21. Nsc 256439

22. Ncgc00093976-03

23. Unii-5vv3mdu5ie

24. Idarubicin Hydrochloride Pfs

25. Sr-01000075934

26. Idamycin (tn)

27. Einecs 260-990-7

28. Idarubicin Hydrochlorid

29. Idarubicin Hydrochloride [usan:usp:inn]

30. Schembl4838

31. Mls000759470

32. Chembl1200976

33. Dtxsid0047797

34. Chebi:31686

35. Kuc110342c

36. Ex-a1148

37. Tox21_111236

38. Idarubicin Hydrochloride [mi]

39. Mfcd00897212

40. S1228

41. Idarubicin Hydrochloride (jp17/usp)

42. Idarubicin Hydrochloride [jan]

43. Akos025402118

44. Tox21_111236_1

45. Ac-5255

46. Ccg-100886

47. Cs-1061

48. Idarubicin Hydrochloride [usan]

49. Nc00136

50. Daunomycin, 4-demethoxy-, Hydrochloride

51. Idarubicin Hydrochloride [mart.]

52. Idarubicin Hydrochloride [vandf]

53. Idarubicin Hydrochloride [usp-rs]

54. Idarubicin Hydrochloride [who-dd]

55. Ncgc00093976-08

56. (1s,3s)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside, Hydrochloride

57. As-75944

58. Hy-17381

59. Ksc-230-185-1

60. Idarubicin Hydrochloride [orange Book]

61. D01747

62. Idarubicin Hydrochloride [usp Monograph]

63. 852i570

64. Q-101407

65. Sr-01000075934-5

66. 4-demethoxydaunorubicin (nsc256439, 4-dmdr) Hcl

67. Q27262943

68. (7s,9s)-9-acetyl-7-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

69. (7s,9s)-9-acetyl-7-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dionehydrochloride

70. (7s,9s)-9-acetyl-7-((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

71. (7s-cis)-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxynaphthacene-5,12-dione Hydrochloride

72. 1s,3s)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranoside, Hydrochloride

73. 5,12-naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxyhydrochloride, (7s-cis)-

74. 5,12-naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxyhydrochloride, (7s-cis)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 534.0 g/mol
Molecular Formula C26H28ClNO9
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Exact Mass533.1452592 g/mol
Monoisotopic Mass533.1452592 g/mol
Topological Polar Surface Area177 Ų
Heavy Atom Count37
Formal Charge0
Complexity912
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 2  
Drug NameIdarubicin hydrochloride
Drug LabelIDAMYCIN PFS Injection contains idarubicin hydrochloride and is a sterile, semi-synthetic, preservative-free solution (PFS) antineoplastic anthracycline for intravenous use. Chemically, idarubicin hydrochloride is 5, 12- Naphthacenedione, 9-acetyl-7-...
Active IngredientIdarubicin hydrochloride
Dosage FormInjectable
RouteInjection
Strength1mg/ml
Market StatusPrescription
CompanySandoz; Fresenius Kabi Usa; Onco Therapies; Eurohlth Intl

2 of 2  
Drug NameIdarubicin hydrochloride
Drug LabelIDAMYCIN PFS Injection contains idarubicin hydrochloride and is a sterile, semi-synthetic, preservative-free solution (PFS) antineoplastic anthracycline for intravenous use. Chemically, idarubicin hydrochloride is 5, 12- Naphthacenedione, 9-acetyl-7-...
Active IngredientIdarubicin hydrochloride
Dosage FormInjectable
RouteInjection
Strength1mg/ml
Market StatusPrescription
CompanySandoz; Fresenius Kabi Usa; Onco Therapies; Eurohlth Intl

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Antibiotics, Antineoplastic

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


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

API Reference Price

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06-Sep-2022
08-Aug-2024
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