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Chemistry

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Also known as: 25316-40-9, Doxorubicin hcl, Rubex, Adriacin, Adriblastina, Caelyx
Molecular Formula
C27H30ClNO11
Molecular Weight
580.0  g/mol
InChI Key
MWWSFMDVAYGXBV-RUELKSSGSA-N
FDA UNII
82F2G7BL4E

Doxorubicin Hydrochloride
Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN.
1 2D Structure

Doxorubicin Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(7S,9S)-7-[(2R,4S,5S,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-RUELKSSGSA-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
82F2G7BL4E
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Adriablastin

2. Adriablastine

3. Adriamycin

4. Adriblastin

5. Adriblastina

6. Adriblastine

7. Adrimedac

8. Doxo Cell

9. Doxo-cell

10. Doxolem

11. Doxorubicin

12. Doxorubicin Hexal

13. Doxorubicin Nc

14. Doxorubicina Ferrer Farm

15. Doxorubicina Funk

16. Doxorubicina Tedec

17. Doxorubicine Baxter

18. Doxotec

19. Farmiblastina

20. Hydrochloride, Doxorubicin

21. Myocet

22. Onkodox

23. Ribodoxo

24. Rubex

25. Urokit Doxo Cell

26. Urokit Doxo-cell

2.3.2 Depositor-Supplied Synonyms

1. 25316-40-9

2. Doxorubicin Hcl

3. Rubex

4. Adriacin

5. Adriblastina

6. Caelyx

7. Doxil

8. Adriamycin Hydrochloride

9. Doxorubicin (adriamycin) Hcl

10. Adriamycin, Hydrochloride

11. Doxorubicin (hydrochloride)

12. Hydroxydaunorubicin Hydrochloride

13. Adriablastina Cs

14. Adriblastin

15. Nsc 123127

16. Hydroxydaunomycin Hydrochloride

17. Mls001401460

18. 82f2g7bl4e

19. Adm Hydrochloride

20. Lipodox

21. Smr000058570

22. Adriamycin Pfs

23. Adriamycin Rdf

24. Dsstox_cid_10636

25. Dsstox_rid_78854

26. Dsstox_rid_80678

27. Dsstox_gsid_30636

28. Dsstox_gsid_45111

29. (8s,10s)-10-(((2r,4s,5s,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

30. (8s,10s)-10-{[(2r,4s,5s,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

31. Adrosal

32. Duxocin

33. Doxorubicin Citric Acid Salt

34. Adriamycin Hydrochloride-dna Complex

35. Mls000028393

36. Mfcd00077757

37. Lipo-dox

38. Fi 6804

39. (7s,9s)-7-[(2r,4s,5s,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

40. (8s-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione Hydrochloride

41. Nsc-123127

42. Sr-01000003049

43. Kw-125

44. Unii-82f2g7bl4e

45. Resmycin

46. Ccris 740

47. Doxorubicin.hcl

48. Doxorubicin Hydrochloride [jan]

49. Doxorubicin, Hcl

50. Adriamycin (tn)

51. Adriacin (tn)

52. (1s,3s)-3-glycoloyl-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

53. (8s,10s)-10-((2r,4s,5s,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

54. (8s-cis)-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione Hydrochloride

55. Prestwick_188

56. Einecs 246-818-3

57. Doxorubicin Hydrochloride [usp:jan]

58. Doxil (tn)

59. Rubex (tn)

60. Cpd000058570

61. Adriblastina Hydrochloride

62. (8s,10s)-10-(((2r,4s,5s,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-tetrahydrotetracen

63. Dox

64. Adriamycin [iarc]

65. Doxorubicini Hydrochloridum

66. Ncgc00163543-01

67. Schembl3242

68. Cas-25316-40-9

69. Mls000049969

70. Mls000049970

71. Mls000049971

72. Mls000070047

73. Mls000392861

74. Mls000392871

75. Mls000392881

76. Mls000392891

77. Mls000392901

78. Mls000759533

79. Mls001055359

80. Doxorubicin Hydrochloride,(s)

81. Chembl359744

82. Dtxsid3030636

83. Chebi:31522

84. Doxorubicin Hydrochloride- Bio-x

85. Doxorubicin Hydrochloride Solution

86. Liposomal Doxorubicin Hydrochloride

87. Bcpp000429

88. Hms1569g18

89. Kuc110341c

90. Ex-a1337

91. Tox21_110050

92. Tox21_112061

93. Tox21_202483

94. Adriamycin (doxorubicin Hydrochloride

95. S1208

96. Akos007930231

97. Akos015920241

98. Doxorubicin Hydrochloride (jp17/usp)

99. Tox21_110050_1

100. Bcp9000237

101. Ccg-100975

102. Cs-1239

103. Nc00225

104. 2-chloro-4-fluorobenzenesulphonylchloride

105. Doxorubicin Hydrochloride [mart.]

106. Doxorubicin Hydrochloride [vandf]

107. Doxorubicin Hydrochloride Liposome

108. Ncgc00014486-01

109. Ncgc00024415-33

110. Ncgc00024415-36

111. Ncgc00260032-01

112. Ncgc00263918-03

113. (8s,10s)-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride

114. As-31687

115. Bd164391

116. Doxorubicin Hydrochloride [usp-rs]

117. Doxorubicin Hydrochloride [who-dd]

118. Doxorubicin Hydrochloride [who-ip]

119. Hy-15142

120. Ksc-230-184-1

121. Doxorubicin Hydrochloride [ema Epar]

122. D01275

123. Doxorubicin Hydrochloride [ep Monograph]

124. Doxorubicin Hydrochloride [orange Book]

125. Doxorubicin Hydrochloride [usp Monograph]

126. 316d409

127. A817779

128. Doxorubicin Hydrochloride Liposome [vandf]

129. Doxorubicin Liposomal Complex Of The Hydrochloride

130. Doxorubicini Hydrochloridum [who-ip Latin]

131. Doxorubicin Hydrochloride, 98.0-102.0% (hplc)

132. Imx-110 Component Doxorubicin Hydrochloride

133. Liposomal Doxorubicin Hydrochloride [who-dd]

134. Sr-01000003049-5

135. Q27032359

136. Sr-01000003049-10

137. Z1557399790

138. Doxorubicin Liposomal Complex Of The Hydrochloride [mi]

139. Doxorubicin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

140. Doxorubicin Hydrochloride, Suitable For Fluorescence, 98.0-102.0% (hplc)

141. Doxorubicin Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

142. Doxorubicin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

143. (8s,10s)-10-(((2r,4s,5s,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

144. (8s,10s)-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride

145. 10-[(3-amino-2,3,6-trideoxy-?-l-lyxohexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-5,12-naphthacenedione Hydrochloride

146. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxylacetyl)-1-methoxy-, Hydrochloride (8s-cis)-

147. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s,10s)-

148. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s-cis)-

149. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxylacetyl)-1-methoxy-, Hydrochloride (8s-cis)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 580.0 g/mol
Molecular Formula C27H30ClNO11
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count5
Exact Mass579.1507385 g/mol
Monoisotopic Mass579.1507385 g/mol
Topological Polar Surface Area206 Ų
Heavy Atom Count40
Formal Charge0
Complexity977
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 NameDoxorubicin hydrochloride
PubMed HealthDoxorubicin Hydrochloride Liposome (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDoxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius. Doxorubicin consists of a naphthacenequinone nucleus linked through a glycosidic bond at ring atom 7 to an amino sugar, daunosamine. Ch...
Active IngredientDoxorubicin hydrochloride
Dosage FormInjectable
RouteInjection
Strength2mg/ml; 10mg/vial; 200mg/100ml; 50mg/vial; 20mg/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Pharmachemie Bv; Onco Therapies; Sun Pharm Inds; Teva Pharms Usa; Sagent Pharms; Eurohlth Intl; Alvogen; Sandoz; Actavis

2 of 2  
Drug NameDoxorubicin hydrochloride
PubMed HealthDoxorubicin Hydrochloride Liposome (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelDoxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius. Doxorubicin consists of a naphthacenequinone nucleus linked through a glycosidic bond at ring atom 7 to an amino sugar, daunosamine. Ch...
Active IngredientDoxorubicin hydrochloride
Dosage FormInjectable
RouteInjection
Strength2mg/ml; 10mg/vial; 200mg/100ml; 50mg/vial; 20mg/vial
Market StatusPrescription
CompanyFresenius Kabi Usa; Pharmachemie Bv; Onco Therapies; Sun Pharm Inds; Teva Pharms Usa; Sagent Pharms; Eurohlth Intl; Alvogen; Sandoz; Actavis

4.2 Drug Indication

Myocet liposomal, in combination with cyclophosphamide, is indicated for the first-line treatment of metastatic breast cancer in adult women.


Caelyx pegylated liposomal is indicated:

- as monotherapy for patients with metastatic breast cancer , where there is an increased cardiac risk;

- for treatment of advanced ovarian cancer in women who have failed a first-line platinum-based chemotherapy regimen;

- in combination with bortezomib for the treatment of progressive multiple myeloma in patients who have received at least one prior therapy and who have already undergone or are unsuitable for bone marrow transplant;

- for treatment of AIDS-related Kaposis sarcoma (KS) in patients with low CD4 counts (< 200 CD4 lymphocytes/mm3) and extensive mucocutaneous or visceral disease.

Caelyx pegylated liposomal may be used as first-line systemic chemotherapy, or as second line chemotherapy in AIDS-KS patients with disease that has progressed with, or in patients intolerant to, prior combination systemic chemotherapy comprising at least two of the following agents: a vinca alkaloid, bleomycin and standarddoxorubicin (or other anthracycline).


Treatment of breast and ovarian cancer .


Treatment of hepatocellular carcinoma


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]
5.3 ATC Code

L01DB01


L01DB


L01DB01


USDMF

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GDUFA

DMF Review : Complete

Rev. Date : 2017-10-18

Pay. Date : 2015-12-28

DMF Number : 13209

Submission : 1998-04-30

Status : Active

Type : II

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DMF Review : Complete

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Pay. Date : 2012-11-13

DMF Number : 13211

Submission : 1998-04-30

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DMF Number : 24128

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DMF Review : Complete

Rev. Date : 2012-11-29

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DMF Number : 13726

Submission : 1998-09-01

Status : Active

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DMF Number : 13773

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Status : Active

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2023-03-06
714
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Certificate Number : R1-CEP 2004-059 - Rev 03

Status : Valid

Issue Date : 2023-03-06

Type : Chemical

Substance Number : 714

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Certificate Number : R0-CEP 2006-181 - Rev 00

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API Reference Price

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04-Jan-2021
31-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - INJECTABLE;INJECTION - 150MG/75ML

USFDA APPLICATION NUMBER - 50629

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DOSAGE - INJECTABLE;INJECTION - 200MG/100ML

USFDA APPLICATION NUMBER - 50629

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DOSAGE - INJECTABLE;INJECTION - 2MG/ML

USFDA APPLICATION NUMBER - 50629

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DOSAGE - INJECTABLE, LIPOSOMAL;INJECTION - 20...DOSAGE - INJECTABLE, LIPOSOMAL;INJECTION - 20MG/10ML (2MG/ML)

USFDA APPLICATION NUMBER - 50718

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DOSAGE - INJECTABLE, LIPOSOMAL;INJECTION - 50...DOSAGE - INJECTABLE, LIPOSOMAL;INJECTION - 50MG/25ML (2MG/ML)

USFDA APPLICATION NUMBER - 50718

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