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Merck

D1515

Doxorubicin hydrochloride

98.0-102.0% (HPLC)

Synonym(s):

Adriamycin, DOX, Hydroxydaunorubicin hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
25316-40-9
Molecular Weight:
579.98
UNSPSC Code:
51281818
NACRES:
NA.76
PubChem Substance ID:
24893465
EC Number:
246-818-3
Beilstein/REAXYS Number:
4229251
MDL number:
MFCD00077757

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Product Name

Doxorubicin hydrochloride, 98.0-102.0% (HPLC)

InChI key

MWWSFMDVAYGXBV-RUELKSSGSA-N

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

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

biological source

synthetic (organic)

assay

98.0-102.0% (HPLC)

form

powder

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

Quality Level

200

Gene Information

human ... TOP2A(7153)

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Preparation Note

Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible
Soluble in water and in isotonic sodium chloride solution, slightly soluble in methanol. Practically insoluble in chloroform, ether, and in other organic solvents.

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.

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.

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive. Light sensitive.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000458096
0000458096
0000397933
0000169094
0000305889

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Consumers Guide to Cancer Drugs (2004)
Poly (ethylene glycol)-conjugated multi-walled carbon nanotubes as an efficient drug carrier for overcoming multidrug resistance
Cheng J, et al.
Toxicology and Applied Pharmacology, 250(2), 184-193 (2011)
Current Pharmaceutical Design (1999)
The release behavior of doxorubicin hydrochloride from medicated fibers prepared by emulsion-electrospinning
Xu X, et al.
European Journal of Pharmaceutics and Biopharmaceutics, 70(1), 165-170 (2008)
In vitro study of anticancer drug doxorubicin in PLGA-based microparticles
Lin R, et al.
Biomaterials, 26(21), 4476-4485 (2005)
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