Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

D1515

Sigma-Aldrich

Doxorubicin hydrochloride

98.0-102.0% (HPLC)

Synonym(s):

Adriamycin, DOX, Hydroxydaunorubicin hydrochloride

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
Molecular Weight:
579.98
Beilstein/REAXYS Number:
4229251
EC Number:
MDL number:
UNSPSC Code:
51281818
PubChem Substance ID:
NACRES:
NA.76

biological source

synthetic (organic)

Quality Level

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

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)

Looking for similar products? Visit Product Comparison Guide

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.

Storage and Stability

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

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.

Related product

Product No.
Description
Pricing

comparable product

pictograms

Health hazardExclamation mark

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Loss of TBL1XR1 disrupts glucocorticoid receptor recruitment to chromatin and results in glucocorticoid resistance in a B-lymphoblastic leukemia model
Jones CL, et al.
The Journal of Biological Chemistry, jbc-M114 (2014)
Principles and Practice of Gynecologic Oncology (2005)
Cancer Chemotherapy: A Nursing Process Approach (2001)
Multifunctional polymer-capped mesoporous silica nanoparticles for pH-responsive targeted drug delivery
Niedermayer S, et al.
Nanoscale, 7(17), 7953-7964 (2015)
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)

Articles

Quinolones are a key group of antibiotics that interfere with DNA synthesis by inhibiting topoisomerase, most frequently topoisomerase II (DNA gyrase), an enzyme involved in DNA replication.

Graphene oxide is a unique material that can be viewed as a single monomolecular layer of graphite with various oxygen containing functionalities such as epoxide, carbonyl, carboxyl and hydroxyl groups.

We presents an article on ABC Transporters and Cancer Drug Resistance

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service