DAUNORUBICIN CITRATE

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 Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=CC=CC2=C1C(=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)=C3C2=O

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	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model.	2004-01-01	14728974
Impact of neutropenia on delivering planned adjuvant chemotherapy: UK audit of primary breast cancer patients.	2003-12-01	14647139
Cardiac troponin T as an indicator of reduced left ventricular contractility in experimental anthracycline-induced cardiomyopathy.	2003-11	14618274
Liposomal daunorubicin (DaunoXome) in multiple myeloma: a modified VAD regimen using short-term infusion.	2003-11	14597873
OSI-211, a novel liposomal topoisomerase I inhibitor, is active in SCID mouse models of human AML and ALL.	2003-11	12859997
Neurotoxicity of intrathecal methotrexate: MR imaging findings.	2003-10	14561622
Population pharmacokinetics of liposomal daunorubicin in children.	2003-10	12968981
Pilot study of gemtuzumab ozogamicin, liposomal daunorubicin, cytarabine and cyclosporine regimen in patients with refractory acute myelogenous leukemia.	2003-10	12860007
Potentiation of tumour apoptosis by human growth hormone via glutathione production and decreased NF-kappaB activity.	2003-09-15	12966434
From conventional to stealth liposomes: a new frontier in cancer chemotherapy.	2003-08-12	12908776
Safety of high-dose liposomal daunorubicin (daunoxome) for refractory or relapsed acute myeloblastic leukaemia.	2003-07	12823360
Daunorubicin-induced variations in gene transcription: commitment to proliferation arrest, senescence and apoptosis.	2003-06-15	12656675
Cytotoxic drugs enhance the ex vivo sensitivity of malignant cells from a subset of acute myeloid leukaemia patients to apoptosis induction by tumour necrosis factor receptor-related apoptosis-inducing ligand.	2003-06	12780785
Multiple alterations of canalicular membrane transport activities in rats with CCl(4)-induced hepatic injury.	2003-04	12642476
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.	2003-04	12531223
The dose related effect of steroids on blast reduction rate and event free survival in children with acute lymphoblastic leukemia.	2003-03	12688320
Efficacy and toxicity of liposomal daunorubicin included in PVABEC regimen for aggressive NHL of the elderly.	2003-03	12688316
[Successful treatment after acute promyelocytic leukemia (APL) syndrome of relapsed API with arsenic trioxide].	2003-03	12669407
Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey.	2003-03	12657726
Different effects of metabolic inhibitors and cyclosporin A on daunorubicin transport in leukemia cells from patients with AML.	2003-02	12526924
Effects of carvedilol on MDR1-mediated multidrug resistance: comparison with verapamil.	2003-01	12708479
Vincristine neurotoxicity in the presence of hereditary neuropathy.	2003-01	12426685
Disposition of liposomal daunorubicin during cotreatment with cytarabine in patients with leukaemia.	2003	12882589
High-dose daunorubicin as liposomal compound (Daunoxome) in elderly patients with acute lymphoblastic leukemia.	2003	12692520
Determination of free and liposome-associated daunorubicin and daunorubicinol in plasma by capillary electrophoresis.	2002-12-06	12498269
Comparative study of chronic toxic effects of daunorubicin and doxorubicin in rabbits.	2002-12	12540035
Comparison of anthracycline-induced death of human leukemia cells: programmed cell death versus necrosis.	2002-12	12370496
Liposomal daunorubicin overcomes drug resistance in human breast, ovarian and lung carcinoma cells.	2002-11	12519627
Resistance of bcr-abl-positive acute lymphoblastic leukemia to daunorubicin is not mediated by mdr1 gene expression.	2002-11	12410571
Induction of metallothionein by zinc protects from daunorubicin toxicity in rats.	2002-09-30	12204545
Nucleotide triphosphatase/helicase of hepatitis C virus as a target for antiviral therapy.	2002-09	12206878
Liposomal daunorubicin (DaunoXome) for treatment of relapsed meningeal acute myeloid leukemia.	2002-09	12200714
[Liposomal daunorubicine combined with cytarabine in the treatment of relapsed/refractory acute myeloid leukemia in children].	2002-08-08	12165900
Liposomal daunorubicin (DaunoXome) for treatment of poor-risk acute leukemia.	2002-08	12224004
Subcellular daunorubicin distribution and its relation to multidrug resistance phenotype in drug-resistant cell line SMMC-7721/R.	2002-08	12174371
Reversible vincristine-related flaccid paralysis in a child with acute lymphoblastic leukemia.	2002-08	12116067
Reversal of multidrug resistance-associated protein-mediated daunorubicin resistance by camptothecin.	2002-08	12115804
A phase I dose-escalating study of DaunoXome, liposomal daunorubicin, in metastatic breast cancer.	2002-07-01	12085249
Monitoring daunorubicin-induced alterations in protein expression in pancreas carcinoma cells by two-dimensional gel electrophoresis.	2002-06	12112851
Influence of chemosensitizers on resistance mechanisms in daunorubicin-resistant Ehrlich ascites tumour cells.	2002-06	12107549
Liposomal daunorubicin (DaunoXome) plus dexamethasone for patients with multiple myeloma. A phase II International Oncology Study Group study.	2002-05-15	12173332
Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells.	2002-05	12088114
NTPase/helicase of Flaviviridae: inhibitors and inhibition of the enzyme.	2002	12422230
Effect of aging on cardiac contractility in a rat model of chronic daunorubicin cardiotoxicity.	2002	12271153
Correlation of histopathological and biochemical appraisal of anthracyclin-induced myocardium damage.	2002	12056608
Bradycardia due to anthracyclines.	1992-10-03	1357285
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.	1992-05-29	1376118
Tumorigenicity in vivo and induction of malignant transformation and mutagenesis in cell cultures by adriamycin and daunomycin.	1976-06	1268859
Daunorubicin-induced cardiotoxicity.	1976-03	1266211
The cardiotoxicity of adriamycin and daunomycin in children.	1976-02	1253124

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 18:13:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:44 GMT 2025`
Record UNII	5L84T2Z6NP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DAUNORUBICIN CITRATE

Common Name

English

DAUNORUBICIN CITRATE LIPOSOME

Preferred 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 [MART.]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

73693