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Merck
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Key Documents

D8809

Sigma-Aldrich

Daunorubicin hydrochloride

meets USP testing specifications

Synonyme(s) :

Daunomycin hydrochloride

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About This Item

Formule empirique (notation de Hill):
C27H29NO10 · HCl
Numéro CAS:
Poids moléculaire :
563.98
Numéro Beilstein :
4229221
Numéro CE :
Numéro MDL:
Code UNSPSC :
41116107
ID de substance PubChem :
Nomenclature NACRES :
NA.21

Agence

USP/NF
meets USP testing specifications

Niveau de qualité

Forme

solid

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

DNA synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

GUGHGUXZJWAIAS-QQYBVWGSSA-N

Informations sur le gène

human ... TOP2A(7153)

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Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazard

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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


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Consulter la Bibliothèque de documents

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
Michal Hayun et al.
Scientific reports, 10(1), 8349-8349 (2020-05-21)
Selection of resistant clones following intensive chemotherapy is a common obstacle for cure in many cancers, particularly in acute myeloid leukemia (AML). In AML, clone-specific sensitivity to chemotherapy varies even within the same patient. Multiple mutations and genetic aberrations are
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

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