DAUNORUBICIN

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 Search

SMILES

COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)C(C)=O)C(O)=C3C(=O)C2=CC=C1

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
Sources: https://www.drugs.com/dosage/daunorubicin.html
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

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260166	Inhibitor 8504
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7932544	Inhibitor 8504
Multidrug resistance-associated protein 1 15 Target ID: CHEMBL3004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9647783	Inhibitor 8504	70.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute lymphoblastic leukemia 27 Sources: https://www.drugs.com/dosage/daunorubicin.html	Primary	Approved 8583	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 1979
Acute myeloblastic leukemia 3 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050467s070lbl.pdf	Primary	Approved 8583	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 1979
Neuroblastoma 26 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050467s070lbl.pdf	Primary	Approved 8583	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 1979

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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	unhealthy, 10 Health Status: unhealthy Age Group: 10 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16880787	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
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	unhealthy, 10 Health Status: unhealthy Age Group: 10 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16880787	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
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	unhealthy, 27-87 Health Status: unhealthy Age Group: 27-87 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf	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
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	unhealthy, 38.7 Health Status: unhealthy Age Group: 38.7 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf	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
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 Sources: https://pubmed.ncbi.nlm.nih.gov/14597873	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14597873	Sources: https://pubmed.ncbi.nlm.nih.gov/14597873
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 Sources: https://pubmed.ncbi.nlm.nih.gov/14597873	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/14597873	DLT: Acute diverticular perforation... Dose limiting toxicities: Acute diverticular perforation Sources: https://pubmed.ncbi.nlm.nih.gov/14597873
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 Sources: https://pubmed.ncbi.nlm.nih.gov/12173332	unhealthy, 63 Health Status: unhealthy Age Group: 63 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12173332	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050718s033lbl.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499	BCRP 697	CYP3A5 92

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11770832/	yes [IC50 203 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12134946/	yes [Ki 49.4 uM]
CYP3A5 201	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12859862/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11437380/	yes

Sourcing

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

PubMed

Title	Date	PubMed
[Effects of all-trans retinoic acid, arsenic trioxide and daunorubicin on tissue factor expression in NB4 cells].	1999 Sep	11721405
TEL/AML1 gene fusion is related to in vitro drug sensitivity for L-asparaginase in childhood acute lymphoblastic leukemia.	2000 Aug 1	10910927
Focal degradation of cytoplasmic organelles in cardiomyocytes during regenerative and plastic myocardial insufficiency.	2000 Dec	11276319
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	10914541
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	10881002
Comparison of anthracycline-induced death of human leukemia cells: programmed cell death versus necrosis.	2002 Dec	12370496
Role of exogenous melatonin in reducing the cardiotoxic effect of daunorubicin and doxorubicin in the rat.	2002 Feb	11926284
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	11841431
Phase IV study of liposomal daunorubicin (DaunoXome) in AIDS-related Kaposi sarcoma.	2002 Feb	11823698
A novel, extraneuronal role for cyclin-dependent protein kinase 5 (CDK5): modulation of cAMP-induced apoptosis in rat leukemia cells.	2002 Jun 7	11909854
Liposomal encapsulation diminishes daunorubicin-induced generation of reactive oxygen species, depletion of ATP and necrotic cell death in human leukaemic cells.	2002 May	11972515
Resistance of bcr-abl-positive acute lymphoblastic leukemia to daunorubicin is not mediated by mdr1 gene expression.	2002 Nov	12410571
Vincristine neurotoxicity in the presence of hereditary neuropathy.	2003 Jan	12426685
Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model.	2004 Jan 1	14728974

Patents

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 `Mon Mar 31 18:22:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:58 GMT 2025`
Record UNII	ZS7284E0ZP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAUNORUBICIN

Official Name

English

VYXEOS COMPONENT DAUNORUBICIN

Preferred 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

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