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1. Cerubidine
2. Dauno Rubidomycine
3. Dauno-rubidomycine
4. Daunoblastin
5. Daunoblastine
6. Daunomycin
7. Daunorubicin Hydrochloride
8. Hydrochloride, Daunorubicin
9. Nsc 82151
10. Nsc-82151
11. Nsc82151
12. Rubidomycin
13. Rubomycin
1. Daunomycin
2. 20830-81-3
3. Acetyladriamycin
4. Leukaemomycin C
5. Rubidomycin
6. Cerubidine
7. (+)-daunomycin
8. Daunoxome
9. Daunorubicinum
10. Daunorubicine
11. Rp 13057
12. Rubomycin C
13. Fi 6339
14. Daunorubicin (inn)
15. Nsc-82151
16. Daunarubicinum
17. Daunorrubicina
18. Daunoxome (tn)
19. Daunamycin
20. Fi-6339
21. Fi6339
22. Rp-13057
23. Zs7284e0zp
24. (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
25. (8s-cis)-8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
26. Chebi:41977
27. Ncgc00024246-05
28. Anthracyline
29. Ndc-0082-4155
30. Dsstox_cid_2883
31. Daunorubicin [inn]
32. Dsstox_rid_76773
33. Dsstox_gsid_22883
34. 5,12-naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-
35. Daunorubicinum [inn-latin]
36. Mls000069508
37. Daunorubicin [inn:ban]
38. Nsc-83142
39. Rcra Waste No. U059
40. (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-alpha-l-lyxo-hexopyranoside
41. Cas-20830-81-3
42. Nsc82151
43. Smr000058559
44. Ccris 914
45. Sr-01000000033
46. Sr-05000001600
47. Hsdb 5095
48. Nci-c04693
49. Einecs 244-069-7
50. Nsc 83142
51. Vs-103
52. Brn 1445583
53. Tocris-1467
54. Daunorubicin(daunomycin)
55. Ai3-52942
56. (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
57. Prestwick3_000487
58. Daunomycin [iarc]
59. Daunorubicin [mi]
60. Chembl178
61. Daunorubicin [hsdb]
62. Schembl3041
63. Daunorubicin [vandf]
64. Epirubicin Impurity D
65. Unii-zs7284e0zp
66. Bspbio_000353
67. Daunorubicin [mart.]
68. 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)-
69. Cid_62770
70. Daunorubicin [who-dd]
71. Bpbio1_000389
72. Gtpl7063
73. Dtxsid7022883
74. Bdbm32017
75. Ex-a1337a
76. Valrubicin Impurity, Daunorubicin
77. Daunorubicin [orange Book]
78. Hms2089h04
79. Hms2091k06
80. Pharmakon1600-01500223
81. Vyxeos Component Daunorubicin
82. Zinc3917708
83. Tox21_110896
84. Bdbm50368352
85. Gr-318
86. Hy-13062a
87. Lmpk13050002
88. Mfcd00866340
89. Nsc756717
90. Tox21_110896_1
91. Ccg-212559
92. Cs-2004
93. Db00694
94. Nsc-756717
95. Ncgc00024246-06
96. Ncgc00024246-07
97. Ncgc00024246-09
98. Ncgc00024246-10
99. Ncgc00024246-12
100. Ncgc00024246-15
101. Ncgc00024246-18
102. Ncgc00025173-01
103. (1s,3s)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside
104. (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
105. (7s,9r)-9-acetyl-7-[(2s,4s,5s,6s)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione
106. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione
107. 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,10s)-
108. Sbi-0206677.p002
109. Ab00514669
110. 30d813
111. C01907
112. D07776
113. Epirubicin Hydrochloride Impurity, Daunorubicin-
114. Ab00514669-09
115. Ab01644616_09
116. Ab01644616_10
117. A814957
118. Q411659
119. Sr-01000000033-4
120. Sr-05000001600-1
121. Sr-05000001600-2
122. Brd-k43389675-001-01-3
123. Brd-k43389675-003-02-7
124. Brd-k43389675-003-03-5
125. Brd-k43389675-003-20-9
126. Epirubicin Hydrochloride Impurity D [ep Impurity]
127. Valrubicin Impurity, Daunorubicin [usp Impurity]
128. 2-hydroxy-5-(4-nitro-phenylsulfamoyl)-benzoicacid
129. Doxorubicin Hydrochloride Impurity A [ep Impurity]
130. Epirubicin Hydrochloride Impurity, Daunorubicin- [usp Impurity]
131. (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
132. (7s,9s)-7-[(2r,4s,5s,6s)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-4-methoxy-6,9,11-tris(oxidanyl)-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride
133. (7s,9s)-9-acetyl-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chloride
134. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-quinone;hydrochloride
135. (7s,9s)-9-acetyl-7-[[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride
136. (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
137. (8s,10s)-8-acetyl-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
138. (8s,10s)-8-acetyl-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
139. (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
140. 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)-
| Molecular Weight | 527.5 g/mol |
|---|---|
| Molecular Formula | C27H29NO10 |
| XLogP3 | 1.8 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 4 |
| Exact Mass | 527.17914612 g/mol |
| Monoisotopic Mass | 527.17914612 g/mol |
| Topological Polar Surface Area | 186 Ų |
| Heavy Atom Count | 38 |
| 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 | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Cerubidine |
| PubMed Health | Daunorubicin (Injection) |
| Drug Classes | Antineoplastic Agent |
| Active Ingredient | Daunorubicin hydrochloride |
| Dosage Form | Injectable |
| Route | Injection |
| Strength | eq 20mg base/vial |
| Market Status | Prescription |
| Company | Eurohlth Intl |
| 2 of 4 | |
|---|---|
| Drug Name | Daunoxome |
| PubMed Health | Daunorubicin Citrate Liposome (Injection) |
| Drug Classes | Antineoplastic Agent |
| Active Ingredient | Daunorubicin citrate |
| Dosage Form | Injectable, liposomal |
| Route | Injection |
| Strength | eq 2mg base/ml |
| Market Status | Prescription |
| Company | Galen (uk) |
| 3 of 4 | |
|---|---|
| Drug Name | Cerubidine |
| PubMed Health | Daunorubicin (Injection) |
| Drug Classes | Antineoplastic Agent |
| Active Ingredient | Daunorubicin hydrochloride |
| Dosage Form | Injectable |
| Route | Injection |
| Strength | eq 20mg base/vial |
| Market Status | Prescription |
| Company | Eurohlth Intl |
| 4 of 4 | |
|---|---|
| Drug Name | Daunoxome |
| PubMed Health | Daunorubicin Citrate Liposome (Injection) |
| Drug Classes | Antineoplastic Agent |
| Active Ingredient | Daunorubicin citrate |
| Dosage Form | Injectable, liposomal |
| Route | Injection |
| Strength | eq 2mg base/ml |
| Market Status | Prescription |
| Company | Galen (uk) |
Antibiotics, Antineoplastic
National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)
Cerubidine in combination with other approved anticancer drugs is indicated for remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. /Included in US product label/
US Natl Inst Health; DailyMed. Current Medication Information for Cerubidine (daunorubicin hydrochloride) injection, powder, for solution (November 2007). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5821
DaunoXome is indicated as a first line cytotoxic therapy for advanced HIV-associated Kaposi's sarcoma. DaunoXome is not recommended in patients with less than advanced HIV-related Kaposi's sarcoma. /Included in US product label/
US Natl Inst Health; DailyMed. Current Medication Information for Daunoxome (daunorubicin citrate) injection, lipid complex (June 2006). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=628
An 8-month-old baby with symptoms of Letterer-Siwe's disease responded dramatically after a 5-day course of daunorubicin, 1 mg per kg body-weight daily. A second course was given 2 weeks later.
Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 205
Cerubidine must be given into a rapidly flowing intravenous infusion. It must never be given by the intramuscular or subcutaneous route. Severe local tissue necrosis will occur if there is extravasation during administration.
US Natl Inst Health; DailyMed. Current Medication Information for Cerubidine (daunorubicin hydrochloride) injection, powder, for solution (November 2007). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5821
Myocardial toxicity manifested in its most severe form by potentially fatal congestive heart failure may occur either during therapy or months to years after termination of therapy. The incidence of myocardial toxicity increases after a total cumulative dose exceeding 400 to 550 mg/sq m in adults, 300 mg/sq m in children more than 2 years of age, or 10 mg/kg in children less than 2 years of age.
US Natl Inst Health; DailyMed. Current Medication Information for Cerubidine (daunorubicin hydrochloride) injection, powder, for solution (November 2007). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5821
Cardiac function should be monitored regularly in patients receiving DaunoXome (daunorubicin citrate liposome injection) because of the potential risk for cardiac toxicity and congestive heart failure. Cardiac monitoring is advised especially in those patients who have received prior anthracyclines or who have pre-existing cardiac disease or who have had prior radiotherapy encompassing the heart.
US Natl Inst Health; DailyMed. Current Medication Information for Daunoxome (daunorubicin citrate) injection, lipid complex (June 2006). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=628
Severe myelosuppression occurs when used in therapeutic doses; this may lead to infection or hemorrhage.
US Natl Inst Health; DailyMed. Current Medication Information for Cerubidine (daunorubicin hydrochloride) injection, powder, for solution (November 2007). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5821
For more Drug Warnings (Complete) data for DAUNORUBICIN (45 total), please visit the HSDB record page.
For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. Daunorubicin is indicated in combination with [cytarabine] for the treatment of newly-diagnosed therapy-related acute myeloid leukemia (t-AML) or AML with myelodysplasia-related changes (AML-MRC) in adults and pediatric patients 1 year and older.
Daunorubicin is an anthracycline antibiotic and antineoplastic agent. It acts by inhibiting cellular reproduction through interference with DNA replication although it may contribute to the induction of cell death by increasing oxidative stress through the generation of reactive oxygen species and free radicals. As an antineoplastic agent, daunorubicin carries significant toxicities including cytopenias, hepatotoxicity, and extravasation reactions. Like other anthracyclines, daunorubicin also exhibits cardiotoxicity in proportion with the cumulative dose received over time.
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.)
L01DB02
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
L - Antineoplastic and immunomodulating agents
L01 - Antineoplastic agents
L01D - Cytotoxic antibiotics and related substances
L01DB - Anthracyclines and related substances
L01DB02 - Daunorubicin
Absorption
Daunorubicin was found to have a tmax of 2 h and a cmax of 24.8 g/mL after a 90 min infusion of the liposomal formulation at a dose of 44 mg/m2.
Route of Elimination
Daunorubicin is eliminated hepatically. 40% of daunorubicin is excreted in the bile while 25% is excreted in an active form (daunorubicin or daunorubicinol) in the urine. In the liposomal formulation, only 9% of active molecules are excreted in the urine.
Volume of Distribution
Daunorubicin has a steady-state volume of distribution of 1.91 L/m2 reported with the liposomal formulation. The average volume of distribution reported for the liposomal formulation is 6.6 L.
Clearance
Daunorubicin has a clearance of 68.4 mL/h/m2 determined using the liposomal formulation.
Note: Liposomal encapsulation can substantially affect a drug's functional properties relative to those of the unencapsulated drug. In addition, different liposomal drug products may vary from one another in the chemical composition and physical form of the liposomes. Such differences can substantially affect the functional properties of liposomal drug products.
US Natl Inst Health; DailyMed. Current Medication Information for Daunoxome (daunorubicin citrate) injection, lipid complex (June 2006). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=628
Encapsulation of daunorubicin citrate in liposomes substantially alters the pharmacokinetics of the drug relative to conventional iv formulations (ie, nonencapsulated drug) with resultant decreased distribution into the peripheral compartment, increased distribution into Kaposi's lesions, and decreased plasma clearance
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
Daunorubicin hydrochloride is extremely irritating to tissues and, therefore, must be administered iv. Following iv infusion of a single 40-mg/sq m dose of liposomal daunorubicin citrate as a liposomal injection in patients with AIDS-related Kaposi's sarcoma, mean peak plasma daunorubicin (mostly bound to liposomes) concentrations are approximately 18 mug/mL following a 30-60 minute infusion. Peak plasma concentrations of daunorubicin are higher following iv administration of liposomal daunorubicin citrate than those attained following iv administration of conventional (nonencapsulated) daunorubicin hydrochloride.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
In one study in patients with disseminated malignancies receiving a single 80-mg/sq m iv dose of nonencapsulated daunorubicin, peak plasma concentrations of the drug were 0.4 ug/mL while in patients with solid tumors (including those with Kaposi's sarcoma) who received a single 80-mg/sq m iv dose of liposomal daunorubicin, peak plasma concentrations of daunorubicin were about 44 ug/mL (about 100-fold greater than those receiving a comparable dose of the nonencapsulated drug); area under the plasma concentration-time curve (AUC) was about 36-fold greater than that observed with conventional daunorubicin hydrochloride. Following iv administration of liposomal daunorubicin, peak plasma concentrations and AUCs of daunorubicin generally increase linearly with increasing doses (at doses of 10-80 ug/mL).
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
For more Absorption, Distribution and Excretion (Complete) data for DAUNORUBICIN (18 total), please visit the HSDB record page.
Daunorubicin hydrochloride is extensively metabolized in the liver and other tissues, mainly by cytoplasmic aldo-keto reductases, producing daunorubicinol, the major metabolite which has antineoplastic activity. Approximately 40% of the drug in the plasma is present as daunorubicinol within 30 minutes and 60% in 4 hours after a dose of nonencapsulated daunorubicin.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
Daunorubicinol has been detected only in low concentrations in the plasma following iv administration of daunorubicin citrate liposomal injection. In patients with AIDS-associated Kaposi's sarcoma receiving iv administration of liposomal daunorubicin doses of 40 mg/sq m, the AUC of daunorubicinol represented only 2% of the total daunorubicin AUC. Additional metabolism by reductive cleavage of the glycosidic bond produces aglycones, which have little or no cytotoxic activity and are demethylated and conjugated with sulfate and glucuronide by microsomal enzymes.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
Metabolites identified in human urine are daunorubicinol, daunorubicinol aglycone, desmethyldeoxydaunorubicinol aglycone, desmethyldeoxyrubicinol aglycone-4-o-sulfate, desmethyloxydaunorubicinol aglycone-4-o-glucuronide, and deoxydaunorubicinol aglycone glucuronide.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 150 (1976)
Extensively metabolized, initially to active alcohol metabolites; further metabolized by liver microsomes to inactive aglycones and demethylated glucuronide and sulfate conjugates.
Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 401
Daunorubicin has been determined to have a terminal half-life of 18.5 h (+/- 4.9). Daunorubicinol, the primary active metabolite has been determined to have a terminal half-life of 26.7 h (+/- 12.8). The mean half-life of elimination of liposomal daunorubicin has been reported to be 22.1 h in pharmacokinetic studies and 31.5 h in official FDA labeling.
Following rapid iv administration of conventional daunorubicin hydrochloride injection, total plasma concentrations of daunorubicin and its metabolites decline in a triphasic manner, and plasma concentrations of unchanged daunorubicin decline in a biphasic manner.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
The plasma half-life of nonencapsulated daunorubicin averages 45 minutes in the initial phase and 18.5 hours in the terminal phase. By 1 hour after administration of nonencapsulated daunorubicin, the predominant form of the drug in plasma is the active metabolite daunorubicinol, which has an average terminal plasma half-life of 26.7 hours.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
The apparent elimination half-life of DaunoXome (daunorubicin citrate liposome injection) is 4.4 hours, far shorter than that of daunorubicin, and probably represents a distribution half-life.
US Natl Inst Health; DailyMed. Current Medication Information for Daunoxome (daunorubicin citrate) injection, lipid complex (June 2006). Available from, as of October 3, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=628
Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
Daunorubicin is an antineoplastic antibiotic. Daunorubicin has antimitotic and cytotoxic activity. Daunorubicin forms a complex with DNA by intercalation between base pairs. By stabilizing the complex between DNA and topoisomerase II, daunorubicin inhibits the activity of this enzyme, resulting in single-strand and double-strand breaks in DNA. Daunorubicin also may inhibit polymerase activity, affect regulation of gene expression, and be involved in free radical damage to DNA. Although daunorubicin is maximally cytotoxic in the S phase, the drug is not cycle-phase specific. Daunorubicin also has antibacterial and immunosuppressive properties.
American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)
Anthracyclines are an important reagent in many chemotherapy regimes for treating a wide range of tumors. One of the primary mechanisms of anthracycline action involves DNA damage caused by inhibition of topoisomerase II. Enzymatic detoxification of anthracycline is a major critical factor that determines anthracycline resistance. Natural product, daunorubicin a toxic analogue of anthracycline is reduced to less toxic daunorubicinol by the AKR1B10, enzyme, which is overexpressed in most cases of smoking associate squamous cell carcinoma (SCC) and adenocarcinoma. In addition, AKR1B10 was discovered as an enzyme overexpressed in human liver, cervical and endometrial cancer cases in samples from uterine cancer patients. Also, the expression of AKR1B10 was associated with tumor recurrence after surgery and keratinization of squamous cell carcinoma in cervical cancer and estimated to have the potential as a tumor intervention target colorectal cancer cells (HCT-8) and diagnostic marker for non-small-cell lung cancer. This article presents the mechanism of daunorubicin action and a method to improve the effectiveness of daunorubicin by modulating the activity of AKR1B10.
PMID:19442055 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6205813 Balendiran GK; Curr Cancer Drug Targets 9 (3): 366-9 (2009).
... In the present study using the ATP depleting agents cyanide, azide, or dinitrophenol to inhibit energy dependent transport processes, /investigators/ observed even larger increases in daunorubicin accumulation than were seen with CsA. Similar patterns were seen in a wide range of P-gp negative human cancer cell lines. Also the observed cyanide effect did not correlate with the expression of mRNA for multidrug resistance-associated protein (MRP), the only other member of the ABC family of membrane transporters that is known to be capable of effluxing daunorubicin. Thse results suggest that daunorubicin accumulation in many cases of AML is modulated by one or more novel energy-dependent processes that are distinct from P-gp or MRP. /The authors/ speculate that this novel drug transport mechanism(s) may influence the response of AML patients to daunorubicin and other therapeutic agents.
PMID:9001418 Hedley DW et al; Leukemia 11 (1): 48-53 (1997).
Inhibits DNA synthesis and blocks DNA-directed RNA polymerase. It can prevent cell division in doses that do not interfere with nucleic acid synthesis.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1086
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