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30450

Sigma-Aldrich

Daunorubicin hydrochloride

≥90% (HPLC)

Synonym(s):

Daunomycin hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H29NO10 · HCl
CAS Number:
23541-50-6
Molecular Weight:
563.98
Beilstein:
4229221
EC Number:
245-723-4
MDL number:
MFCD04974507
UNSPSC Code:
51102829
PubChem Substance ID:
57648441
NACRES:
NA.85

biological source

synthetic

Assay

≥90% (HPLC)

form

powder

color

red to deep red

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O

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

InChI key

GUGHGUXZJWAIAS-QQYBVWGSSA-N

Gene Information

human ... TOP2A(7153)

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General description

Chemical structure: aminoglycoside

Application

Daunorubicin hydrochloride is used in photostability, antileukemic, and drug metabolism studies.

Biochem/physiol Actions

On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Daunomycin effectively binds to every 3 base pairs which causes unwinding.
Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent.

Packaging

5 mg, 25 mg

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Store under inert gas.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H341,H351,H360FD

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Photoprotection of Daunorubicin Hydrochloride with Sodium Sulfite.
Mohammad S. Islam* and Ahmed F. Asker
Journal of Pharmaceutical Sciences, 49, 122-126 (1995)
I-Shan Hsieh et al.
Molecular pharmacology, 83(5), 968-977 (2013-02-26)
Multidrug resistance is a major cause of chemotherapy failure. Recent studies indicate that drug resistance can be rapidly induced by some soluble factors, such as cytokines, chemokines, growth factors, and cell adhesion factors in the tumor microenvironment. Osteopontin (OPN), an
Sarah Bertoli et al.
Blood, 121(14), 2618-2626 (2013-02-01)
In acute myeloid leukemia (AML), new strategies assess the potential benefit of genetically targeted therapy at diagnosis. This implies waiting for laboratory tests and therefore a delay in initiation of chemotherapy. We studied the impact of time from diagnosis to
Oliver Teuffel et al.
British journal of haematology, 161(2), 192-203 (2013-02-13)
This systematic review and meta-analysis compared the efficacy of different anthracyclines and anthracycline dosing schedules for induction therapy in acute myeloid leukaemia in children and adults younger than 60 years of age. Twenty-nine randomized controlled trials were eligible for inclusion in
Kevin W H Yee et al.
Blood, 104(13), 4202-4209 (2004-08-12)
Fetal liver tyrosine kinase 3 internal tandem duplication (FLT3 ITD) mutations are the most common molecular abnormality associated with adult acute myeloid leukemia (AML). To exploit this molecular target, a number of potent and specific FLT3 kinase inhibitors have been
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