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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.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
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
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

PubMed

PubMed

TitleDatePubMed
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
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
Bradycardia due to anthracyclines.
1992 Oct 3
NTPase/helicase of Flaviviridae: inhibitors and inhibition of the enzyme.
2002
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
Liposomal daunorubicin (DaunoXome) for treatment of poor-risk acute leukemia.
2002 Aug
Subcellular daunorubicin distribution and its relation to multidrug resistance phenotype in drug-resistant cell line SMMC-7721/R.
2002 Aug
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
A phase I dose-escalating study of DaunoXome, liposomal daunorubicin, in metastatic breast cancer.
2002 Jul 1
[Liposomal daunorubicine combined with cytarabine in the treatment of relapsed/refractory acute myeloid leukemia in children].
2002 Jul-Aug
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 (DaunoXome) plus dexamethasone for patients with multiple myeloma. A phase II International Oncology Study Group study.
2002 May 15
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
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
Multiple alterations of canalicular membrane transport activities in rats with CCl(4)-induced hepatic injury.
2003 Apr
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
Different effects of metabolic inhibitors and cyclosporin A on daunorubicin transport in leukemia cells from patients with AML.
2003 Feb
Effects of carvedilol on MDR1-mediated multidrug resistance: comparison with verapamil.
2003 Jan
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
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 Jun
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
Cardiac troponin T as an indicator of reduced left ventricular contractility in experimental anthracycline-induced cardiomyopathy.
2003 Nov
Liposomal daunorubicin (DaunoXome) in multiple myeloma: a modified VAD regimen using short-term infusion.
2003 Nov
OSI-211, a novel liposomal topoisomerase I inhibitor, is active in SCID mouse models of human AML and ALL.
2003 Nov
Neurotoxicity of intrathecal methotrexate: MR imaging findings.
2003 Oct
Population pharmacokinetics of liposomal daunorubicin in children.
2003 Oct
Pilot study of gemtuzumab ozogamicin, liposomal daunorubicin, cytarabine and cyclosporine regimen in patients with refractory acute myelogenous leukemia.
2003 Oct
Potentiation of tumour apoptosis by human growth hormone via glutathione production and decreased NF-kappaB activity.
2003 Sep 15
Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model.
2004 Jan 1
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 Oct 21 20:59:31 UTC 2019
Edited
by admin
on Mon Oct 21 20:59:31 UTC 2019
Record UNII
5L84T2Z6NP
Record Status Validated (UNII)
Record Version
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Name Type Language
DAUNORUBICIN CITRATE
MART.   ORANGE BOOK   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 [WHO-DD]
Common 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 Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
FDA ORPHAN DRUG 266508
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
FDA ORPHAN DRUG 393413
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
NCI_THESAURUS C1594
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
EU-Orphan Drug EU/3/08/585
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
Code System Code Type Description
RXCUI
221087
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
CAS
371770-68-2
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL178
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
NCI_THESAURUS
C47471
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
PUBCHEM
9961878
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
RXCUI
1364321
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
ALTERNATIVE
RXCUI
214468
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
ALTERNATIVE
EVMPD
SUB22734
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
EPA CompTox
371770-68-2
Created by admin on Mon Oct 21 20:59:31 UTC 2019 , Edited by admin on Mon Oct 21 20:59:31 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC