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Epirubicin

Synopsis, Chemistry

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INJECTABLE;INJECTION - 200MG/100ML (2MG/ML), INJECTABLE;INJECTION - 50MG/25ML (2MG/ML)

INJECTABLE;INJECTION - 200MG/100ML (2MG/ML)
INJECTABLE;INJECTION - 50MG/25ML (2MG/ML)

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Also known as: Pharmorubicin, 56390-09-1, Ellence, Epirubicin hcl, Farmorubicin, Farmorubicina

Molecular Formula

C₂₇H₃₀ClNO₁₁

Molecular Weight

580.0 g/mol

InChI Key

MWWSFMDVAYGXBV-FGBSZODSSA-N

FDA UNII

22966TX7J5

An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.

1 2D Structure

Epirubicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

2.1.2 InChI

InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22-,27-;/m0./s1

2.1.3 InChI Key

MWWSFMDVAYGXBV-FGBSZODSSA-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)CO)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)CO)O)N)O.Cl

2.2 Other Identifiers

2.2.1 UNII

22966TX7J5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4' Epi Adriamycin

2. 4' Epi Doxorubicin

3. 4' Epi Dxr

4. 4' Epiadriamycin

5. 4' Epidoxorubicin

6. 4'-epi-adriamycin

7. 4'-epi-doxorubicin

8. 4'-epi-dxr

9. 4'-epiadriamycin

10. 4'-epidoxorubicin

11. Ellence

12. Epi Cell

13. Epi-cell

14. Epicell

15. Epilem

16. Epirubicin

17. Farmorubicin

18. Farmorubicina

19. Farmorubicine

20. Hydrochloride, Epirubicin

21. Imi 28

22. Imi-28

23. Imi28

24. Nsc 256942

25. Nsc-256942

26. Nsc256942

27. Pharmorubicin

2.3.2 Depositor-Supplied Synonyms

1. Pharmorubicin

2. 56390-09-1

3. Ellence

4. Epirubicin Hcl

5. Farmorubicin

6. Farmorubicina

7. Imi-28

8. 4'-epidoxorubicin Hydrochloride

9. Epirubicin Ebewe

10. Epirubicin (hydrochloride)

11. Nsc-759195

12. Mls001401404

13. Nsc 256942

14. Pidorubicin

15. Wp-697

16. 22966tx7j5

17. 4'-epi-adriamycin Hydrochloride

18. Smr000466308

19. 56390-09-1 (hcl)

20. (8s,10s)-10-(((2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

21. Epirubitec

22. 4'-epi-adriamycin

23. Epidoxorubicin Hydrochloride

24. (7s,9s)-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

25. Ccris 4477

26. Einecs 260-145-2

27. Unii-22966tx7j5

28. Ellence (tn)

29. 4'-epi-doxorubicin

30. Epirubicin Hydrochlorid

31. 4'-epidoxorubicin Hcl

32. Cpd000466308

33. Epirubicin Hydrochloride [usan:usp:jan]

34. E-adm

35. 4'-epi-dx

36. Schembl3165

37. (1s,3s)-3-glycoloyl-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-arabino-hexopyranoside Hydrochloride

38. Mls000759412

39. 4-epidoxorubicin Hydrochloride

40. Epirubicin Hcl [vandf]

41. Chembl1200981

42. Dtxsid50860297

43. Pharmakon1600-01505708

44. Amy10308

45. Ex-a2654

46. Epirubicin Hcl (4'-epidoxorubicin)

47. Epirubicin Hydrochloride [mi]

48. Hy-13624a

49. Mfcd00941448

50. Nsc759195

51. S1223

52. Epirubicin Hydrochloride (jp17/usp)

53. Epirubicin Hydrochloride [jan]

54. Bcp9000651

55. Ccg-100950

56. Cs-1773

57. Epirubicin Hydrochloride [usan]

58. Nc00200

59. Epirubicin Hydrochloride [mart.]

60. Epirubicin Hydrochloride [usp-rs]

61. Epirubicin Hydrochloride [who-dd]

62. (8s-cis)-10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione Hydrochloride

63. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s-cis)-

64. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-arabinohexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s,10s)-

65. As-75323

66. Epirubicin Hydrochloride, >=90% (hplc)

67. E0840

68. Epirubicin Hydrochloride [orange Book]

69. D02214

70. D83113

71. Epirubicin Hydrochloride [ep Monograph]

72. Epirubicin Hydrochloride [usp Monograph]

73. Sr-01000763557

74. Q-101406

75. Sr-01000763557-3

76. Q27253634

77. Epirubicin Hydrochloride, British Pharmacopoeia (bp) Reference Standard

78. Epirubicin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

79. Epirubicin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

80. (1s,3s)-3-glycoloyl-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-arabino-hexopyranoside Hydrochloride

81. (8s,10s)-10-(((2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dionehydrochloride

82. (8s,10s)-10-((2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

83. (8s,10s)-10-{[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione Hydrochloride

84. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s-cis)-

85. 5,12-naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, Hydrochloride (1:1), (8s,10s)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₀ClNO₁₁
Molecular Weight	580.0 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	5
Exact Mass	579.1507385 g/mol
Monoisotopic Mass	579.1507385 g/mol
Topological Polar Surface Area	206 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	977
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 4
Drug Name	Ellence
Drug Label	ELLENCE Injection (epirubicin hydrochloride injection) is an anthracycline cytotoxic agent, intended for intravenous administration. ELLENCE is supplied as a sterile, clear, red solution and is available in polypropylene vials containing 50 and 200 m...
Active Ingredient	Epirubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml)
Market Status	Prescription
Company	Pfizer

2 of 4
Drug Name	Epirubicin hydrochloride
Drug Label	Epirubicin hydrochloride injection is an anthracycline cytotoxic agent, intended for intravenous administration. Epirubicin hydrochloride injection is supplied as a sterile, clear, red solution and is available invials containing 50 mg and 200 mg o...
Active Ingredient	Epirubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml); 150mg/75ml (2mg/ml); 10mg/5ml (2mg/ml)
Market Status	Prescription
Company	Actavis Elizabeth; Fresenius Kabi Usa; Hospira; Fresenius Kabi Oncol; Ebewe Pharma; Onco Therapies; Teva Pharms Usa; Eurohlth Intl; Cipla; Hisun Pharm Hangzhou; Akorn

3 of 4
Drug Name	Ellence
Drug Label	ELLENCE Injection (epirubicin hydrochloride injection) is an anthracycline cytotoxic agent, intended for intravenous administration. ELLENCE is supplied as a sterile, clear, red solution and is available in polypropylene vials containing 50 and 200 m...
Active Ingredient	Epirubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml)
Market Status	Prescription
Company	Pfizer

4 of 4
Drug Name	Epirubicin hydrochloride
Drug Label	Epirubicin hydrochloride injection is an anthracycline cytotoxic agent, intended for intravenous administration. Epirubicin hydrochloride injection is supplied as a sterile, clear, red solution and is available invials containing 50 mg and 200 mg o...
Active Ingredient	Epirubicin hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	200mg/100ml (2mg/ml); 50mg/25ml (2mg/ml); 150mg/75ml (2mg/ml); 10mg/5ml (2mg/ml)
Market Status	Prescription
Company	Actavis Elizabeth; Fresenius Kabi Usa; Hospira; Fresenius Kabi Oncol; Ebewe Pharma; Onco Therapies; Teva Pharms Usa; Eurohlth Intl; Cipla; Hisun Pharm Hangzhou; Akorn

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

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

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Anthracyclines [CS]; Topoisomerase Inhibitors [MoA]; Anthracycline Topoisomerase Inhibitor [EPC]