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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO10.ClH
Molecular Weight 563.981
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAUNORUBICIN HYDROCHLORIDE

SMILES

Cl.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=GUGHGUXZJWAIAS-QQYBVWGSSA-N
InChI=1S/C27H29NO10.ClH/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;1H/t10-,14-,16-,17-,22+,27-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
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
Myocardial injury produced by antineoplastic drugs.
1975
The cardiotoxicity of adriamycin and daunomycin in children.
1976 Feb
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
[Effects of all-trans retinoic acid, arsenic trioxide and daunorubicin on tissue factor expression in NB4 cells].
1999 Sep
Fractionated cyclophosphamide, vincristine, liposomal daunorubicin (daunoXome), and dexamethasone (hyperCVXD) regimen in Richter's syndrome.
2001 Jul
Liposomal daunorubicin (DaunoXome) in combination with cyclophosphamide, vincristine and prednisolone (COP-X) as salvage therapy in poor-prognosis non-Hodgkins lymphoma.
2001 Jun
Benign thymic hyperplasia after chemotherapy for acute myeloid leukemia.
2001 Oct
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
Effects of dietary lipids on daunomycin-induced nephropathy in mice: comparison between cod liver oil and soybean oil.
2002 Apr
Comparison of idarubicin and daunorubicin regarding intracellular uptake, induction of apoptosis, and resistance.
2002 Apr 25
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
Role of exogenous melatonin in reducing the cardiotoxic effect of daunorubicin and doxorubicin in the rat.
2002 Feb
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
Influence of chemosensitizers on resistance mechanisms in daunorubicin-resistant Ehrlich ascites tumour cells.
2002 Jun
A novel, extraneuronal role for cyclin-dependent protein kinase 5 (CDK5): modulation of cAMP-induced apoptosis in rat leukemia cells.
2002 Jun 7
Liposomal encapsulation diminishes daunorubicin-induced generation of reactive oxygen species, depletion of ATP and necrotic cell death in human leukaemic 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
Nucleotide triphosphatase/helicase of hepatitis C virus as a target for antiviral therapy.
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
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
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
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
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
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 Tue Oct 22 00:38:10 UTC 2019
Edited
by admin
on Tue Oct 22 00:38:10 UTC 2019
Record UNII
UD984I04LZ
Record Status Validated (UNII)
Record Version
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Name Type Language
DAUNORUBICIN HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official 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 HYDROCHLORIDE
Common Name English
DAUNORUBICIN HYDROCHLORIDE [WHO-DD]
Common Name English
DAUNORUBICIN HCL
Common Name English
NDC-0082-4155
Code English
RP 13057 HYDROCHLORIDE
Code English
DAUNORUBICIN HYDROCHLORIDE [VANDF]
Common Name English
DAUNORUBICIN HYDROCHLORIDE [MART.]
Common Name English
DAUNORUBICIN HYDROCHLORIDE [USAN]
Common Name English
DAUNORUBICIN HYDROCHLORIDE [EP]
Common Name English
DAUNORUBICIN (AS HYDROCHLORIDE)
Common Name English
NDC 0082-4155
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)-, HYDROCHLORIDE
Common Name English
DAUNORUBICIN HYDROCHLORIDE [MI]
Common Name English
DAUNORUBICIN HYDROCHLORIDE [USP]
Common Name English
NSC-82151
Code English
RP-13057 HYDROCHLORIDE
Code English
FI-6339 HYDROCHLORIDE
Code English
DAUNORUBICIN HYDROCHLORIDE [JAN]
Common Name English
CERUBIDINE
Brand Name English
DAUNORUBICIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
FI 6339 HYDROCHLORIDE
Code English
DAUNORUBICIN HYDROCHLORIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
Code System Code Type Description
MERCK INDEX
M4104
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY Merck Index
EPA CompTox
23541-50-6
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL178
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
ECHA (EC/EINECS)
245-723-4
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
RXCUI
81992
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C1583
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
CAS
23541-50-6
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
EVMPD
SUB01556MIG
Created by admin on Tue Oct 22 00:38:10 UTC 2019 , Edited by admin on Tue Oct 22 00:38:10 UTC 2019
PRIMARY
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