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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO10.C6H8O7
Molecular Weight 719.6434
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAUNORUBICIN CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.[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=VNTHYLVDGVBPOU-QQYBVWGSSA-N
InChI=1S/C27H29NO10.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/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
Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
8146
Inhibitor
8146
Inhibitor
8146
 70.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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
8307
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
8307
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
1532

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MRP2
363
BCRP
545
CYP3A5
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1857
 yes [IC50 203 uM]
MRP2
452
 yes [Ki 49.4 uM]
CYP3A5
130
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
545
 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
[Possibility for the prevention of cardio toxic effect of Cerubidin].
1975 Aug 24
Endomyocardial fibrosis associated with daunorubicin therapy.
1976 Aug
Tumorigenicity in vivo and induction of malignant transformation and mutagenesis in cell cultures by adriamycin and daunomycin.
1976 Jun
IGF-I in experimental daunorubicin-induced cardiomyopathy in rabbits.
1999 Mar
Stress-induced gastric lesion formation is prevented in rats with daunomycin-induced nephrosis.
1999 Oct
Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members.
1999 Oct 15
[Effects of all-trans retinoic acid, arsenic trioxide and daunorubicin on tissue factor expression in NB4 cells].
1999 Sep
TEL/AML1 gene fusion is related to in vitro drug sensitivity for L-asparaginase in childhood acute lymphoblastic leukemia.
2000 Aug 1
Ultrastructure of nuclear compartment in cardiomyocytes during regenerative and plastic insufficiency of the myocardium.
2000 Dec
Focal degradation of cytoplasmic organelles in cardiomyocytes during regenerative and plastic myocardial insufficiency.
2000 Dec
Release of plasminogen activator inhibitor-1 from human astrocytes is regulated by intracellular ceramide.
2000 Dec 15
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.
2000 Jan
Chest and back pain associated with a six-hour infusion of liposomal daunorubicin.
2000 Jun
Epirubicin--docetaxel combination in first-line chemotherapy for patients with metastatic breast cancer: final results of a dose-finding and efficacy study.
2001 Aug
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
Fractionated cyclophosphamide, vincristine, liposomal daunorubicin (daunoXome), and dexamethasone (hyperCVXD) regimen in Richter's syndrome.
2001 Jul
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
Liposomal encapsulated anthracyclines: new therapeutic horizons.
2001 Mar
Benign thymic hyperplasia after chemotherapy for acute myeloid leukemia.
2001 Oct
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
Subcellular daunorubicin distribution and its relation to multidrug resistance phenotype in drug-resistant cell line SMMC-7721/R.
2002 Aug
Reversal of multidrug resistance-associated protein-mediated daunorubicin resistance by camptothecin.
2002 Aug
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
Phase IV study of liposomal daunorubicin (DaunoXome) in AIDS-related Kaposi sarcoma.
2002 Feb
A phase I dose-escalating study of DaunoXome, liposomal daunorubicin, in metastatic breast cancer.
2002 Jul 1
Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells.
2002 May
Liposomal daunorubicin (DaunoXome) plus dexamethasone for patients with multiple myeloma. A phase II International Oncology Study Group study.
2002 May 15
Nucleotide triphosphatase/helicase of hepatitis C virus as a target for antiviral therapy.
2002 Sep
Liposomal daunorubicin (DaunoXome) for treatment of relapsed meningeal acute myeloid leukemia.
2002 Sep
Induction of metallothionein by zinc protects from daunorubicin toxicity in rats.
2002 Sep 30
Disposition of liposomal daunorubicin during cotreatment with cytarabine in patients with leukaemia.
2003
High-dose daunorubicin as liposomal compound (Daunoxome) in elderly patients with acute lymphoblastic leukemia.
2003
A phase I/II study of the MDR modulator Valspodar (PSC 833) combined with daunorubicin and cytarabine in patients with relapsed and primary refractory acute myeloid leukemia.
2003 Apr
Impact of neutropenia on delivering planned adjuvant chemotherapy: UK audit of primary breast cancer patients.
2003 Dec 1
Safety of high-dose liposomal daunorubicin (daunoxome) for refractory or relapsed acute myeloblastic leukaemia.
2003 Jul
Efficacy and toxicity of liposomal daunorubicin included in PVABEC regimen for aggressive NHL of the elderly.
2003 Mar
From conventional to stealth liposomes: a new frontier in cancer chemotherapy.
2003 May-Jun
OSI-211, a novel liposomal topoisomerase I inhibitor, is active in SCID mouse models of human AML and ALL.
2003 Nov
Pilot study of gemtuzumab ozogamicin, liposomal daunorubicin, cytarabine and cyclosporine regimen in patients with refractory acute myelogenous leukemia.
2003 Oct
Patents

Patents

07344699
3
JP2001511768A
13
JP2001512418A
13
JP2001527049A
10
JP2002541200A
12
JP2002541233A
392
JP2002542270A
9
JP2004523497A
78
JP2004532301A
10
JP2006514009A
43
JP2007528354A
9
JP2009526755A
434
JP2010515545A
12
JP2011510954A
140
JP4301440B2
13
JP4527401B2
30
JP4701159B2
69
JP4813746B2
10
JP4818917B2
29
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 Fri Dec 16 18:41:17 UTC 2022
Edited
by admin
on Fri Dec 16 18:41:17 UTC 2022
Record UNII
5L84T2Z6NP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAUNORUBICIN CITRATE
MART.   ORANGE BOOK   WHO-DD  
Common Name English
Daunorubicin Citrate [WHO-DD]
Common Name English
DAUNORUBICIN LIPOSOMAL
Brand Name 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,10S)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Common Name English
DAUNORUBICIN CITRATE [ORANGE BOOK]
Common Name 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,10S)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1) (SALT)
Common Name English
DAUNOXOME
Brand Name English
DAUNORUBICIN CITRATE LIPOSOME
VANDF  
Common Name English
DAUNORUBICIN CITRATE LIPOSOME [VANDF]
Common Name English
DAUNORUBICIN CITRATE [MART.]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 73693
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
FDA ORPHAN DRUG 266508
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
FDA ORPHAN DRUG 393413
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
NCI_THESAURUS C1594
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
EU-Orphan Drug EU/3/08/585
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
Code System Code Type Description
RXCUI
221087
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
CAS
371770-68-2
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
DRUG BANK
DBSALT001476
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
ChEMBL
CHEMBL178
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
NCI_THESAURUS
C47471
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
PUBCHEM
9961878
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
FDA UNII
5L84T2Z6NP
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
RXCUI
1364321
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
ALTERNATIVE
RXCUI
214468
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
ALTERNATIVE
DAILYMED
5L84T2Z6NP
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
EVMPD
SUB22734
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
EPA CompTox
DTXSID20190659
Created by admin on Fri Dec 16 18:41:17 UTC 2022 , Edited by admin on Fri Dec 16 18:41:17 UTC 2022
PRIMARY
Related Record Type Details
Structure of DAUNORUBICIN
PARENT -> SALT/SOLVATE
Structure of ANHYDROUS CITRIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DAUNORUBICIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966