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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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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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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.

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

D1515-10MG: + D1515-VAR: + D1515-10MG-PW: + D1515-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD4494V
WXBD3450V
WXBD1159V
WXBC9779V
079M4838V

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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)
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Inhibition of Nucleic Acid Synthesis by Antibiotics

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