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D8809

Sigma-Aldrich

Daunorubicin hydrochloride

meets USP testing specifications

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:
41116107
PubChem Substance ID:
24894229
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

200

form

solid

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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Biochem/physiol Actions

Naturally fluorescent anthracycline antibiotic, anticancer drug. Substrate for Pgp, MRP-1 and BCRP. Fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles (golgi and lysosome) in the sequestration of drugs and its implication in drug resistant phenotypes. Daunorubicin is sequestered into lysosomes according to a pH partitioning type mechanism. Strong inhibitor of DNA and RNA synthesis.
Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000361849
0000361849
WXBD9789V
0000190373
0000190372

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E J Wang et al.
Drug metabolism and disposition: the biological fate of chemicals, 28(5), 522-528 (2000-04-20)
P-glycoprotein (Pgp)-mediated drug efflux is a major factor contributing to the variance of absorption and distribution of many drugs. A simple and reliable in vitro method to identify inhibitors of Pgp helps to prevent the potential of drug interactions. Using
Devika Prasanth et al.
Life (Basel, Switzerland), 10(9) (2020-08-28)
Microgravity or the condition of apparent weightlessness causes bone, muscular and immune system dysfunctions in astronauts following spaceflights. These organ and system-level dysfunctions correlate with changes induced at the single cell level both by simulated microgravity on earth as well
Yuping Gong et al.
The Journal of biological chemistry, 278(50), 50234-50239 (2003-10-03)
The sequestration of drugs away from cellular target sites into cytoplasmic organelles of multidrug-resistant (MDR) cancer cells has been recently shown to be a cause for ineffective drug therapy. This process is poorly understood despite the fact that it has
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
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
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