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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

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
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
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
Letter: Pericarditis in a case of early daunorubicin cardiomyopathy.
1976 Sep
[Effects of all-trans retinoic acid, arsenic trioxide and daunorubicin on tissue factor expression in NB4 cells].
1999 Sep
Brain natriuretic peptide is a predictor of anthracycline-induced cardiotoxicity.
2000
Anthracyclines trigger apoptosis of both G0-G1 and cycling peripheral blood lymphocytes and induce massive deletion of mature T and B cells.
2000 Apr 1
TEL/AML1 gene fusion is related to in vitro drug sensitivity for L-asparaginase in childhood acute lymphoblastic leukemia.
2000 Aug 1
Characterisation of multidrug-resistant Ehrlich ascites tumour cells selected in vivo for resistance to etoposide.
2000 Aug 1
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
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
Regulation of phospholipase D activity and ceramide production in daunorubicin-induced apoptosis in A-431 cells.
2000 Nov 15
Palmar-plantar erythrodysesthesia syndrome associated with liposomal daunorubicin.
2000 Oct
Prevention by dexrazoxane of down-regulation of ryanodine receptor gene expression in anthracycline cardiomyopathy in the rat.
2000 Sep
Pharmacokinetics of liposomal daunorubicin (DaunoXome) during a phase I-II study in children with relapsed acute lymphoblastic leukaemia.
2001
Phase II trial of liposomal daunorubicin in malignant pleural mesothelioma.
2001 Apr
Daunorubicin attenuates tumor necrosis factor-alpha-induced biosynthesis of plasminogen activator inhibitor-1 in human umbilical vein endothelial cells.
2001 Apr 23
Liposomal anthracyclines for breast cancer.
2001 Aug
Epirubicin--docetaxel combination in first-line chemotherapy for patients with metastatic breast cancer: final results of a dose-finding and efficacy study.
2001 Aug
Ultrastructural changes in cardiomyocyte mitochondria during regenerative and plastic insufficiency of the myocardium.
2001 Feb
High-dose liposomal daunorubicin and high-dose cytarabine combination in patients with refractory or relapsed acute myelogenous leukemia.
2001 Jul 1
Liposomal daunorubicin (DaunoXome) in combination with cyclophosphamide, vincristine and prednisolone (COP-X) as salvage therapy in poor-prognosis non-Hodgkins lymphoma.
2001 Jun
Alterative and plastic insufficiency of cardiomyocytes: isoproterenol-induced damage to myocardium during anthracycline cardiomyopathy.
2001 Jun
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
Effects of dietary lipids on daunomycin-induced nephropathy in mice: comparison between cod liver oil and soybean oil.
2002 Apr
Liposomal daunorubicin (DaunoXome) for treatment of poor-risk acute leukemia.
2002 Aug
Reversible vincristine-related flaccid paralysis in a child with acute lymphoblastic leukemia.
2002 Aug
Comparative study of chronic toxic effects of daunorubicin and doxorubicin in rabbits.
2002 Dec
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
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
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
The dose related effect of steroids on blast reduction rate and event free survival in children with acute lymphoblastic leukemia.
2003 Mar
Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey.
2003 Mar
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 20:57:09 UTC 2019
Edited
by admin
on Mon Oct 21 20:57:09 UTC 2019
Record UNII
ZS7284E0ZP
Record Status Validated (UNII)
Record Version
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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
VALRUBICIN IMPURITY, DAUNORUBICIN [USP]
Common Name English
FI-6339
Code English
NSC-83142
Code English
EPIRUBICIN HYDROCHLORIDE IMPURITY D [EP]
Common Name English
DAUNORUBICIN [MART.]
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY, DAUNORUBICIN- [USP]
Common Name English
DAUNORUBICIN [WHO-DD]
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
DOXORUBICIN HYDROCHLORIDE IMPURITY A [EP]
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 Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
NCI_THESAURUS C1594
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
FDA ORPHAN DRUG 265808
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
WHO-ATC L01DB02
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
WHO-ATC L01XY01
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
NDF-RT N0000000176
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
LIVERTOX 270
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
EU-Orphan Drug EU/3/11/942
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
WHO-VATC QL01DB02
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
Code System Code Type Description
HSDB
20830-81-3
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
INN
2257
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
EVMPD
SUB06917MIG
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
WIKIPEDIA
DAUNORUBICIN
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
ChEMBL
CHEMBL178
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
DRUG BANK
DB00694
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
PUBCHEM
30323
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
EPA CompTox
20830-81-3
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
NCI_THESAURUS
C62091
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
MESH
D003630
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
IUPHAR
7063
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
MERCK INDEX
M4104
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY Merck Index
CAS
20830-81-3
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
RXCUI
3109
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
244-069-7
Created by admin on Mon Oct 21 20:57:09 UTC 2019 , Edited by admin on Mon Oct 21 20:57:09 UTC 2019
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC