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Idarubicin Hydrochloride

Idarubicin Hydrochloride

Synopsis, 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

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 Formula	C₂₆H₂₈ClNO₉
Molecular Weight	534.0 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	3
Exact Mass	533.1452592 g/mol
Monoisotopic Mass	533.1452592 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	912
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Idarubicin hydrochloride
Drug Label	IDAMYCIN 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 Ingredient	Idarubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	1mg/ml
Market Status	Prescription
Company	Sandoz; Fresenius Kabi Usa; Onco Therapies; Eurohlth Intl

2 of 2
Drug Name	Idarubicin hydrochloride
Drug Label	IDAMYCIN 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 Ingredient	Idarubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	1mg/ml
Market Status	Prescription
Company	Sandoz; 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]