U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO10
Molecular Weight 527.5199
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAUNORUBICIN

SMILES

[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(C)=O)O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5

InChI

InChIKey=STQGQHZAVUOBTE-VGBVRHCVSA-N
InChI=1S/C27H29NO10/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/t10-,14-,16-,17-,22+,27-/m0/s1

HIDE SMILES / InChI
Molecular Formula C27H29NO10
Molecular Weight 527.5199
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22260166 | https://www.ncbi.nlm.nih.gov/pubmed/7932544 | https://www.ncbi.nlm.nih.gov/pubmed/13146115 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050467s070lbl.pdf

Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically, it is used for acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. Similar to doxorubicin, daunorubicin interacts with DNA by intercalation and inhibition of macromolecular biosynthesis. This inhibits the progression of the enzyme topoisomerase II, which relaxes supercoils in DNA for transcription. Daunorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of replication. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. It has the highest preference for two adjacent G/C base pairs flanked on the 5' side by an A/T base pair. Daunorubicin should only be administered in a rapid intravenous infusion. It should not be administered intramuscularly or subcutaneously, since it may cause extensive tissue necrosis. It should also never be administered intrathecally (into the spinal canal), as this will cause extensive damage to the nervous system and may lead to death.

CNS Activity

Originator

Approval Year

1979
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
Inhibitor
8228
Inhibitor
8228
 70.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
CERUBIDINE

Approved Use

Daunorubicin hydrochloride injection 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.

Launch Date

3.14409615E11
Primary
Approved
8360
CERUBIDINE

Approved Use

Daunorubicin hydrochloride injection 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.

Launch Date

3.14409615E11
Primary
Approved
8360
CERUBIDINE

Approved Use

Daunorubicin hydrochloride injection 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.

Launch Date

3.14409615E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
26 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf
44 mg/m² 1 times / 2 days multiple, intravenous
dose: 44 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Cytarabine
Cytarabine
 DAUNORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
637 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf
44 mg/m² 1 times / 2 days multiple, intravenous
dose: 44 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Cytarabine
Cytarabine
 DAUNORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
31.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209401s000lbl.pdf
44 mg/m² 1 times / 2 days multiple, intravenous
dose: 44 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Cytarabine
Cytarabine
 DAUNORUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
REVIEW
https://clincancerres.aacrjournals.org/content/clincanres/early/2017/06/26/1078-0432.CCR-16-3083.full.pdf
DAUNORUBICIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
190 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 190 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 190 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
DLT: Neutropenia, Leucopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 100%)
Leucopenia (grade 4, 100%)
Thrombocytopenia (grade 4, 16.7%)
Anemia (grade 4, 16.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
155 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 155 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 155 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
DLT: Neutropenia, Leucopenia...
Disc. AE: Cardiac failure...
Dose limiting toxicities:
Neutropenia (grade 4, 100%)
Leucopenia (grade 4, 50%)
AEs leading to
discontinuation/dose reduction:
Cardiac failure (grade 5, 16.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
unhealthy, 27-87
n = 239
Health Status: unhealthy
Condition: Ovarian Cancer
Age Group: 27-87
Sex: M+F
Population Size: 239
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
Disc. AE: Skin toxicity...
AEs leading to
discontinuation/dose reduction:
Skin toxicity (4.2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
20 mg/m2 1 times / 2 weeks multiple, intravenous
Recommended
Dose: 20 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / 2 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
unhealthy, 38.7
n = 705
Health Status: unhealthy
Condition: AIDS-related Kaposi’s sarcoma
Age Group: 38.7
Sex: M+F
Population Size: 705
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
Disc. AE: Skin eruption...
AEs leading to
discontinuation/dose reduction:
Skin eruption (0.9%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
80 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 80 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 80 mg/m2, 1 times / 3 weeks
Co-administed with::
vincristine, i.v(1.4 mg/m2, day 1)
dexamethasone, p.o(40 mg/day, days 1–4 and 9–12)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
unhealthy, 60
n = 3
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 60
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
vincristine, i.v(1.4 mg/m2, day 1)
dexamethasone, p.o(40 mg/day, days 1–4 and 9–12)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
unhealthy, 60
n = 3
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 60
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
DLT: Acute diverticular perforation...
Dose limiting toxicities:
Acute diverticular perforation
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Disc. AE: Ejection fraction decreased, Prolonged neutropenia...
Other AEs: Granulocytopenia, Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Ejection fraction decreased (5.3%)
Prolonged neutropenia (2.6%)
Other AEs:
Granulocytopenia (grade 4, 21%)
Thrombocytopenia (grade 4, 8%)
Febrile neutropenia (grade 4, 11%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Disc. AE: Infusion related reaction, Myelosuppression...
AEs leading to
discontinuation/dose reduction:
Infusion related reaction (acute)
Myelosuppression (severe)
Cardiotoxicity
Congestive heart failure
Hepatic impairment
Reaction anaphylactic anaphylactoid (grade 3-5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Leucopenia grade 4, 100%
DLT
190 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 190 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 190 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Neutropenia grade 4, 100%
DLT
190 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 190 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 190 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Anemia grade 4, 16.7%
DLT
190 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 190 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 190 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Thrombocytopenia grade 4, 16.7%
DLT
190 mg/m2 1 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 190 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 190 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Neutropenia grade 4, 100%
DLT
155 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 155 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 155 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Leucopenia grade 4, 50%
DLT
155 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 155 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 155 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Cardiac failure grade 5, 16.7%
Disc. AE
155 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 155 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 155 mg/m2, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
unhealthy, 10
n = 6
Health Status: unhealthy
Condition: Cancer
Age Group: 10
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/16880787
Page: p.573, 575
Skin toxicity 4.2%
Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
unhealthy, 27-87
n = 239
Health Status: unhealthy
Condition: Ovarian Cancer
Age Group: 27-87
Sex: M+F
Population Size: 239
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
Skin eruption 0.9%
Disc. AE
20 mg/m2 1 times / 2 weeks multiple, intravenous
Recommended
Dose: 20 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / 2 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
unhealthy, 38.7
n = 705
Health Status: unhealthy
Condition: AIDS-related Kaposi’s sarcoma
Age Group: 38.7
Sex: M+F
Population Size: 705
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.11
Acute diverticular perforation DLT, Disc. AE
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
vincristine, i.v(1.4 mg/m2, day 1)
dexamethasone, p.o(40 mg/day, days 1–4 and 9–12)
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
unhealthy, 60
n = 3
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 60
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/14597873
Page: p.795
Prolonged neutropenia 2.6%
Disc. AE
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Ejection fraction decreased 5.3%
Disc. AE
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Febrile neutropenia grade 4, 11%
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Granulocytopenia grade 4, 21%
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Thrombocytopenia grade 4, 8%
100 mg/m2 1 times / 3 weeks multiple, intravenous
Studied dose
Dose: 100 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / 3 weeks
Co-administed with::
dexamethasone, p.o(40 mg/day, days 1–4)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
unhealthy, 63
n = 38
Health Status: unhealthy
Condition: Multiple myeloma
Age Group: 63
Sex: M+F
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/12173332
Page: p.2648
Cardiotoxicity Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Congestive heart failure Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Hepatic impairment Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Infusion related reaction acute
Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Reaction anaphylactic anaphylactoid grade 3-5
Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Myelosuppression severe
Disc. AE
50 mg/m2 1 times / 4 weeks multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / 4 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Ovarian Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1579

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MRP2
367
BCRP
555
CYP3A5
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1909
 yes [IC50 203 uM]
MRP2
459
 yes [Ki 49.4 uM]
CYP3A5
130
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
555
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:41977
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41977
ChemicalBook
CB0338996
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0338996
ZINC
ZINC000003917708
http://zinc15.docking.org/substances/ZINC000003917708
eMolecules
30152546
https://www.emolecules.com/cgi-bin/more?vid=30152546
PubMed

PubMed

TitleDatePubMed
Myocardial injury produced by antineoplastic drugs.
1975
Endomyocardial fibrosis associated with daunorubicin therapy.
1976 Aug
The cardiotoxicity of adriamycin and daunomycin in children.
1976 Feb
Tumorigenicity in vivo and induction of malignant transformation and mutagenesis in cell cultures by adriamycin and daunomycin.
1976 Jun
Daunorubicin-induced cardiotoxicity.
1976 Mar
Letter: Pericarditis in a case of early daunorubicin cardiomyopathy.
1976 Sep
Bradycardia due to anthracyclines.
1992 Oct 3
Brain natriuretic peptide is a predictor of anthracycline-induced cardiotoxicity.
2000
TEL/AML1 gene fusion is related to in vitro drug sensitivity for L-asparaginase in childhood acute lymphoblastic leukemia.
2000 Aug 1
High-dose cytosine arabinoside and daunorubicin induction therapy for adult patients with de novo non M3 acute myelogenous leukemia: impact of cytogenetics on achieving a complete remission.
2000 Jul
Low-dose daunorubicin in induction treatment of childhood acute lymphoblastic leukemia: no long-term cardiac damage in a randomized study of the Dutch Childhood Leukemia Study Group.
2000 Jul
Chest and back pain associated with a six-hour infusion of liposomal daunorubicin.
2000 Jun
Anthracycline induced cardiomyopathy: successful treatment with angiotensin converting enzyme inhibitors.
2000 May
[Severe hemolysis and SIADH-like symptoms induced by vincristine in an ALL patient with liver cirrhosis].
2000 Nov
Prevention by dexrazoxane of down-regulation of ryanodine receptor gene expression in anthracycline cardiomyopathy in the rat.
2000 Sep
Daunorubicin attenuates tumor necrosis factor-alpha-induced biosynthesis of plasminogen activator inhibitor-1 in human umbilical vein endothelial cells.
2001 Apr 23
Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
2001 Feb
Down-regulation of catalase gene expression in the doxorubicin-resistant AML subline AML-2/DX100.
2001 Feb 16
High-dose liposomal daunorubicin and high-dose cytarabine combination in patients with refractory or relapsed acute myelogenous leukemia.
2001 Jul 1
Separation and determination of liposomal and non-liposomal daunorubicin from the plasma of patients treated with Daunoxome.
2001 Jun 15
Effect of aging on cardiac contractility in a rat model of chronic daunorubicin cardiotoxicity.
2002
Correlation of histopathological and biochemical appraisal of anthracyclin-induced myocardium damage.
2002
Effects of dietary lipids on daunomycin-induced nephropathy in mice: comparison between cod liver oil and soybean oil.
2002 Apr
Reversible vincristine-related flaccid paralysis in a child with acute lymphoblastic leukemia.
2002 Aug
Reversal of multidrug resistance-associated protein-mediated daunorubicin resistance by camptothecin.
2002 Aug
Comparative study of chronic toxic effects of daunorubicin and doxorubicin in rabbits.
2002 Dec
Comparison of anthracycline-induced death of human leukemia cells: programmed cell death versus necrosis.
2002 Dec
Determination of free and liposome-associated daunorubicin and daunorubicinol in plasma by capillary electrophoresis.
2002 Dec 6
Safety and early efficacy assessment of liposomal daunorubicin (DaunoXome) in adults with refractory or relapsed acute myeloblastic leukaemia: a phase I-II study.
2002 Feb
Monitoring daunorubicin-induced alterations in protein expression in pancreas carcinoma cells by two-dimensional gel electrophoresis.
2002 Jun
Influence of chemosensitizers on resistance mechanisms in daunorubicin-resistant Ehrlich ascites tumour cells.
2002 Jun
Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells.
2002 May
Liposomal daunorubicin overcomes drug resistance in human breast, ovarian and lung carcinoma cells.
2002 Nov
Resistance of bcr-abl-positive acute lymphoblastic leukemia to daunorubicin is not mediated by mdr1 gene expression.
2002 Nov
Induction of metallothionein by zinc protects from daunorubicin toxicity in rats.
2002 Sep 30
High-dose daunorubicin as liposomal compound (Daunoxome) in elderly patients with acute lymphoblastic leukemia.
2003
Multiple alterations of canalicular membrane transport activities in rats with CCl(4)-induced hepatic injury.
2003 Apr
Impact of neutropenia on delivering planned adjuvant chemotherapy: UK audit of primary breast cancer patients.
2003 Dec 1
Different effects of metabolic inhibitors and cyclosporin A on daunorubicin transport in leukemia cells from patients with AML.
2003 Feb
Vincristine neurotoxicity in the presence of hereditary neuropathy.
2003 Jan
Safety of high-dose liposomal daunorubicin (daunoxome) for refractory or relapsed acute myeloblastic leukaemia.
2003 Jul
Daunorubicin-induced variations in gene transcription: commitment to proliferation arrest, senescence and apoptosis.
2003 Jun 15
The dose related effect of steroids on blast reduction rate and event free survival in children with acute lymphoblastic leukemia.
2003 Mar
Efficacy and toxicity of liposomal daunorubicin included in PVABEC regimen for aggressive NHL of the elderly.
2003 Mar
[Successful treatment after acute promyelocytic leukemia (APL) syndrome of relapsed API with arsenic trioxide].
2003 Mar
Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey.
2003 Mar
From conventional to stealth liposomes: a new frontier in cancer chemotherapy.
2003 May-Jun
Neurotoxicity of intrathecal methotrexate: MR imaging findings.
2003 Oct
Population pharmacokinetics of liposomal daunorubicin in children.
2003 Oct
Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model.
2004 Jan 1
Patents

Patents

07344699
3
JP2001511768A
17
JP2001512418A
17
JP2001527049A
12
JP2002541200A
14
JP2002541233A
397
JP2002542270A
11
JP2004523497A
81
JP2004532301A
12
JP2006514009A
48
JP2007528354A
11
JP2009526755A
442
JP2010515545A
14
JP2011510954A
142
JP4301440B2
15
JP4527401B2
32
JP4701159B2
70
JP4813746B2
12
JP4818917B2
31
JPH01246295A
3
JPH05105637A
3
JPH06336444A
3
JPS05921394A
3
JPS54141759A
3
JPS58152816A
3
JPS59122423A
3
JPS60226824A
3
JPS617229A
3
JPS617282A
3
JPS62169731A
3

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Acute Nonlymphocytic Leukemia: Under 60 years of age: 45 mg/m2 IV over 2 to 5 minutes once a day on days 1, 2, and 3 for the first course and on days 1 and 2 for subsequent courses) with cytosine arabinoside (ara-C) intravenously once a day (usually for 7 days for the first course and 5 days for subsequent courses) as remission induction therapy.
Route of Administration: Intravenous
In Vitro Use Guide
In order to determine the viability of HL-60, K562, THP-1, and HEK293T cells, they were trypsinized, counted, and seeded into 96-well plates and were treated with serial dilutions (0.0001, 0.001, 0.01, 0.1, 1 mkM) of DNR (Daunorubicin). Cell viability was determined 48 h after DNR treatment using the luminescent cell viability assay (Promega) through luminescence testing by BMG NOVOstar machine.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:42:03 UTC 2023
Edited
by admin
on Wed Jul 05 23:42:03 UTC 2023
Record UNII
ZS7284E0ZP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAUNORUBICIN
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
FI 6339
Code English
RP 13057
Code English
EPIRUBICIN IMPURITY D
Common Name English
DAUNORUBICIN [MI]
Common Name English
(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
Common Name English
DAUNORUBICIN [HSDB]
Common Name English
VYXEOS COMPONENT DAUNORUBICIN
Brand Name English
RP-13057
Code English
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)-
Common Name English
DAUNOMYCIN
Common Name English
FI-6339
Code English
Daunorubicin [WHO-DD]
Common Name English
NSC-83142
Code English
EPIRUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY, DAUNORUBICIN- [USP IMPURITY]
Common Name English
VALRUBICIN IMPURITY, DAUNORUBICIN [USP IMPURITY]
Common Name English
DAUNORUBICIN [MART.]
Common Name English
DOXORUBICIN HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
(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
Common Name English
DAUNORUBICIN [ORANGE BOOK]
Common Name English
DAUNORUBICIN [VANDF]
Common Name English
daunorubicin [INN]
Common Name English
DAUNOMYCIN [IARC]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175414
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
NCI_THESAURUS C1594
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
FDA ORPHAN DRUG 265808
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
WHO-ATC L01DB02
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
NDF-RT N0000007530
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
WHO-ATC L01XY01
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
NDF-RT N0000000176
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
NDF-RT N0000007530
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
LIVERTOX NBK548259
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
NDF-RT N0000007530
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
EU-Orphan Drug EU/3/11/942
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
WHO-VATC QL01DB02
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
Code System Code Type Description
HSDB
5095
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
INN
2257
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
EVMPD
SUB06917MIG
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
WIKIPEDIA
DAUNORUBICIN
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL178
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
DRUG BANK
DB00694
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
PUBCHEM
30323
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID7022883
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
NCI_THESAURUS
C62091
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
MESH
D003630
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
IUPHAR
7063
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
DAILYMED
ZS7284E0ZP
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
NSC
83142
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
MERCK INDEX
M4104
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY Merck Index
FDA UNII
ZS7284E0ZP
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
SMS_ID
100000086006
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
CAS
20830-81-3
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
CHEBI
41977
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
RXCUI
3109
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
786
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
244-069-7
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
CHEBI
64677
Created by admin on Wed Jul 05 23:42:03 UTC 2023 , Edited by admin on Wed Jul 05 23:42:03 UTC 2023
PRIMARY
Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
Structure of DAUNORUBICIN CITRATE
SALT/SOLVATE -> PARENT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of DAUNORUBICIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
MRP-2
TRANSPORTER -> INHIBITOR
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
MRP-1
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of EPIRUBICIN HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DOXORUBICIN HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of VALRUBICIN
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of DAUNORUBICIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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