Merck
All Photos(2)

D1515

Sigma-Aldrich

Doxorubicin hydrochloride

98.0-102.0% (HPLC)

Synonym(s):
DOX, Adriamycin, Hydroxydaunorubicin hydrochloride
Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
Molecular Weight:
579.98
Beilstein:
4229251
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.76

Nível de qualidade

200

fonte biológica

synthetic (organic)

teor

98.0-102.0% (HPLC)

forma

powder

pf

216 °C (dec.) (lit.)

solubilidade

water: 50.0-52.0 mg/mL, clear, orange to red

espectro de atividade do antibiótico

viruses

Modo de ação

DNA synthesis | interferes

temperatura de armazenamento

2-8°C

SMILES string

Cl[H].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(=O)CO

InChI

1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

InChI key

MWWSFMDVAYGXBV-RUELKSSGSA-N

Gene Information

human ... TOP2A(7153)

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Descrição geral

Doxorubicin hydrochloride (DOX) is an anthracycline antibiotic isolated from Streptomyces peucetius var. caesius. The water soluble anti-cancer agent DOX is a hydroxy derivative of daunorubicin.
Chemical structure: tetracycline

Aplicação

Doxorubicin hydrochloride has been used:
  • in cell viability assays
  • MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay
  • as a drug in polymeric PLGA-based microparticulate drug delivery
  • to develop doxorubicin-resistant HepG2 cells (HepG2-DR) and K562 cells (K562-DR)

Embalagem

10 mg in glass bottle

Ações bioquímicas/fisiológicas

Naturally fluorescent anthracycline antibiotic, anticancer drug. Doxorubicin is a substrate of MRP1 which was first cloned from a DOX-resistant lung cancer cell line. 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.
Substrate of MRP1; used for measurement of drug efflux pump activities. Doxorubicin hydrochloride (DOX) inhibits topoisomerase II by intercalating between base pairs and by inducing strand breaks, resulting in the inhibition of nucleic acid and protein synthesis. It also contributes to the formation of free radicals for the disruption of membrane lipids and DNA strands. DOX is used in the treatment of non-Hodgkin′s lymphoma and other cancers.

Nota de preparo

Soluble in water and in isotonic sodium chloride solution, slightly soluble in methanol. Practically insoluble in chloroform, ether, and in other organic solvents.

Outras notas

Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive. Light sensitive.

Pictogramas

Exclamation markHealth hazard

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 4 Oral - Carc. 1B - Muta. 1B - Repr. 1B

Código de classe de armazenamento

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

WGK

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Certificate of Analysis

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Certificate of Origin

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