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Chemistry

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Also known as: 23541-50-6, Daunorubicin hcl, Daunomycin hydrochloride, Cerubidine, Rubidomycin hydrochloride, Rp 13057 hydrochloride

Molecular Formula

C₂₇H₃₀ClNO₁₀

Molecular Weight

564.0 g/mol

InChI Key

GUGHGUXZJWAIAS-QQYBVWGSSA-N

FDA UNII

UD984I04LZ

A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.

1 2D Structure

Daunorubicin HCl

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-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

2.1.2 InChI

InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1

2.1.3 InChI Key

GUGHGUXZJWAIAS-QQYBVWGSSA-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)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=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl

2.2 Other Identifiers

2.2.1 UNII

UD984I04LZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cerubidine

2. Dauno Rubidomycine

3. Dauno-rubidomycine

4. Daunoblastin

5. Daunoblastine

6. Daunomycin

7. Daunorubicin

8. Hydrochloride, Daunorubicin

9. Nsc 82151

10. Nsc-82151

11. Nsc82151

12. Rubidomycin

13. Rubomycin

2.3.2 Depositor-Supplied Synonyms

1. 23541-50-6

2. Daunorubicin Hcl

3. Daunomycin Hydrochloride

4. Cerubidine

5. Rubidomycin Hydrochloride

6. Rp 13057 Hydrochloride

7. Daunomycin Hcl

8. Ndc 0082-4155

9. Rp-13057 Hydrochloride

10. Daunorubicin (hydrochloride)

11. Daunoblastin

12. Ondena

13. Rubomycin

14. Fi 6339 [as The Base]

15. Daunomycin, Hydrochloride

16. Ud984i04lz

17. Daunorubicin (as Hydrochloride)

18. (8s,10s)-8-acetyl-10-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

19. Fi 6339 Hydrochloride

20. Fi-6339 Hydrochloride

21. Daunoxome

22. (8s-cis)-8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride

23. Daunoblastina

24. Nsc-82151

25. Rp 13057 [as The Base]

26. Daunomycin Chlorohydrate

27. Mls000069508

28. Mfcd04974507

29. Rp 13057 [as The Base)

30. Ccris 915

31. Mls001336042

32. Smr000058559

33. Einecs 245-723-4

34. Unii-ud984i04lz

35. C27h29no10.hcl

36. Daunorubicin Hcl (daunomycin Hcl)

37. Ai3-44887

38. Sr-01000000033

39. Sr-05000001600

40. Cerubidine (tn)

41. Daunorubicin,(s)

42. Daunorubicin Hydrochloride(bicins)

43. (8s,10s)-8-acetyl-10-((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

44. (8s,10s)-8-acetyl-10-[[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

45. Smr000768722

46. Daunorubicin Hydrochloride [usan:usp:jan]

47. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

48. Daunorubicin Hcl- Bio-x

49. Schembl4444

50. Cas-23541-50-6

51. Chembl1563

52. Dsstox_cid_13382

53. Dsstox_rid_79068

54. Dsstox_gsid_33382

55. (1s,3s)-3-acetyl-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-lyxo-hexopyranoside Hydrochloride

56. Mls002222263

57. Dtxsid0033382

58. Chebi:31456

59. (8s,10s)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-?-l-lyxo-hexopyransoyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride

60. Ex-a2649

61. Tox21_201159

62. Ccg-39942

63. S3035

64. Akos015920259

65. Cs-1271

66. Daunorubicin Hydrochloride (jp17/usp)

67. Daunorubicin Hydrochloride [mi]

68. Ks-5149

69. Daunorubicin Hydrochloride [jan]

70. Daunorubicin Hydrochloride [usan]

71. Ncgc00024246-03

72. Ncgc00258711-01

73. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl))oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s-cis)-, Hydrochloride

74. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trhydroxy-1-methoxy-, Hydrochloride, (8s,10s)-

75. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s-cis)-, Hydrochloride

76. Bd164356

77. Daunorubicin Hydrochloride [mart.]

78. Daunorubicin Hydrochloride [vandf]

79. Hy-13062

80. Daunorubicin Hydrochloride [usp-rs]

81. Daunorubicin Hydrochloride [who-dd]

82. Daunorubicin Hydrochloride, >=90% (hplc)

83. D01264

84. Daunorubicin Hydrochloride [orange Book]

85. Wp900 Hydrochloride, >=95% (hplc), Solid

86. Daunorubicin Hydrochloride [ep Monograph]

87. Daunorubicin Hydrochloride [usp Impurity]

88. 541d506

89. A816764

90. Daunorubicin Hydrochloride [usp Monograph]

91. Sr-01000000033-6

92. Sr-05000001600-3

93. Q27291034

94. Daunorubicin Hydrochloride, Meets Usp Testing Specifications

95. Daunorubicin Hydrochloride; Rp 13057 Hydrochloride; Daunomycin

96. Daunorubicin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

97. Daunorubicin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

98. (1s,3s)-3-acetyl-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-lyxo-hexopyranoside Hydrochloride

99. (1s,3s)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranoside Hydrochloride

100. (8s,10s)-8-acetyl-10-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dionehydrochloride

101. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl))oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s-cis)-, Hydrochloride

102. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, Hydrochloride, (8s,10s)-

103. Daunorubicin Hydrochloride;(8s,10s)-8-acetyl-10-[[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₀ClNO₁₀
Molecular Weight	564.0 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	563.1558238 g/mol
Monoisotopic Mass	563.1558238 g/mol
Topological Polar Surface Area	186 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	960
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	Daunorubicin hydrochloride
Drug Label	Daunorubicin Hydrochloride Injection consists of the hydrochloride salt of an anthracycline cytotoxic antibiotic produced by a strain of Streptomyces coeruleorubidus. It is provided as a deep red sterile liquid in vials for intravenous administration...
Active Ingredient	Daunorubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	eq 5mg base/ml; eq 20mg base/vial; eq 5mg base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Teva Pharms Usa; Eurohlth Intl

2 of 2
Drug Name	Daunorubicin hydrochloride
Drug Label	Daunorubicin Hydrochloride Injection consists of the hydrochloride salt of an anthracycline cytotoxic antibiotic produced by a strain of Streptomyces coeruleorubidus. It is provided as a deep red sterile liquid in vials for intravenous administration...
Active Ingredient	Daunorubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	eq 5mg base/ml; eq 20mg base/vial; eq 5mg base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Teva Pharms Usa; 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]

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