Merck
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D1515

Sigma-Aldrich

Doxorubicin hydrochloride

98.0-102.0% (HPLC)

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

biological source

synthetic (organic)

Quality Level

Assay

98.0-102.0% (HPLC)

form

powder

storage condition

(Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible )

mp

216 °C (dec.) (lit.)

solubility

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

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes

storage temp.

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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This Item
44583D2975000PHR1789
Doxorubicin hydrochloride European Pharmacopoeia (EP) Reference Standard

D2975000

Doxorubicin hydrochloride

Doxorubicin Hydrochloride Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1789

Doxorubicin Hydrochloride

assay

98.0-102.0% (HPLC)

assay

98.0-102.0% (HPLC)

assay

-

assay

-

form

powder

form

solid

form

-

form

powder

storage condition

(Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible )

storage condition

-

storage condition

-

storage condition

-

mp

216 °C (dec.) (lit.)

mp

216 °C (dec.) (lit.)

mp

216 °C (dec.) (lit.)

mp

216 °C (dec.) (lit.)

solubility

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

solubility

H2O: 50 mg/mL, clear, orange to red, DMSO: soluble, THF: soluble, ethanol: soluble, methanol: soluble

solubility

-

solubility

-

General description

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.

Doxorubicin also leads to the generation of reactive oxygen species (ROS), which further damage DNA, proteins, and membranes. It exerts cytotoxic, antitumor, anticancer, and antineoplastic activity and finds application in cancer, metabolomics, cell biology, and biochemical research.

Application

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)

Biochem/physiol Actions

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.

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Ideal for Cell Biology, Metabolomics, and Biochemical research.

Preparation Note

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

Other Notes

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

related product

Product No.
Description
Pricing

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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