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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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)
Jay Chhablani et al.
Investigative ophthalmology & visual science, 54(2), 1268-1279 (2013-01-17)
To test the feasibility of covalent loading of daunorubicin into oxidized porous silicon (OPS) and to evaluate the ocular properties of sustained delivery of daunorubicin in this system. Porous silicon was heat oxidized and chemically functionalized so that the functional
Cedric Dos Santos et al.
Blood, 122(11), 1900-1913 (2013-07-31)
The SRC family kinases (SFKs) and the receptor tyrosine kinase c-Kit are activated in human acute myeloid leukemia (AML) cells. We show here that the SFKs LYN, HCK, or FGR are overexpressed and activated in AML progenitor cells. Treatment with
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
Ursula Creutzig et al.
Blood, 122(1), 37-43 (2013-05-25)
Outcomes of patients with acute myeloid leukemia (AML) improve significantly by intensification of induction. To further intensify anthracycline dosage without increasing cardiotoxicity, we compared potentially less cardiotoxic liposomal daunorubicin (L-DNR) to idarubicin at a higher-than-equivalent dose (80 vs 12 mg/m(2)
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