Skip to Content
Merck
All Photos(4)

Key Documents

View All Documentation

44583

Sigma-Aldrich

Doxorubicin hydrochloride

suitable for fluorescence, 98.0-102.0% (HPLC)

Synonym(s):

DOX, Hydroxydaunorubicin hydrochloride

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
25316-40-9
Molecular Weight:
579.98
Beilstein:
4229251
EC Number:
246-818-3
MDL number:
MFCD00077757
UNSPSC Code:
51281818
PubChem Substance ID:
57650234
NACRES:
NA.76

biological source

synthetic

Quality Level

200

Assay

98.0-102.0% (HPLC)

form

solid

color

orange to dark red

mp

216 °C (dec.) (lit.)

solubility

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

fluorescence

λem 580-590 nm

suitability

suitable for fluorescence

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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

Chemical structure: tetracycline

Application

Doxorubicin was used to induce apoptosis, and to induce cardiotoxicity in SK-N-MC cells . It is used to inhibit macromolecular biosynthesis.

Biochem/physiol Actions

Doxorubicin ia an antitumor antibiotic that intercalates DNA and inhibits macromolecular biosynthesis. DNA replication is haulted due to the inhibition of topoisomerase II. It is an inhibitor of reverse transcriptase and RNA polymerase and is an immunosuppressive agent .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H340,H350,H360FD

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

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

Customers Also Viewed

Slide 1 of 2

1 of 2

Daunorubicin hydrochloride European Pharmacopoeia (EP) Reference Standard

D0125000

Daunorubicin hydrochloride

Paclitaxel from semisynthetic, ≥98%

Sigma-Aldrich

T7191

Paclitaxel

R L Momparler et al.
Cancer research, 36(8), 2891-2895 (1976-08-01)
The effect of adriamycin on DNA, RNA, and protein synthesis was investigated in cell-free systems and intact cells. In studies with purified mammalian cell enzymes, adriamycin produced a greater inhibition of DNA-dependent DNA polymerase than of RNA polymerase. The extent
Lisa Fujimura et al.
Cardiovascular research, 64(2), 315-321 (2004-10-16)
The Ndl gene, which encodes a novel kelch family protein, is expressed ubiquitously in mouse tissues. In vitro studies suggest that Ndl protein, which binds to actin filaments, functions as a cytoskeletal stabilizer. In order to elucidate a physiological function
Michael A Skinner et al.
Anticancer research, 28(4B), 2019-2025 (2008-08-30)
Medullary thyroid cancer (MTC) is generally resistant to chemotherapy and the frequent constitutive activation of RET (rearranged during transfection gene) in these tumors might inhibit drug-induced apoptosis. Each RET isoform was separately expressed in SK-N-MC cells (neural crest-derived tumor) and
Shujun Zhang et al.
Journal of natural products, 69(10), 1425-1428 (2006-10-28)
Two new guaianolides, named chinensiolides D (5) and E (6), were isolated from Ixeris chinensis Nakai, and their structures were determined to be 10alpha-hydroxy-3-oxoguaia-11(13)-eno-12,6alpha-lactone (5) and 10alpha-hydroxy-3beta-O-[2,6-di(p-hydroxyphenylacetyl)-beta-glucopylanosyl]guaia-4(15),11(13)-dieno-12,6alpha-lactone (6). The first isolation of (11S)-10alpha-hydroxy-3-oxoguaia-4-eno-12,6alpha-lactone (4) from natural sources and its characterization
C Main et al.
Health technology assessment (Winchester, England), 10(9), 1-132 (2006-03-21)
To examine the clinical effectiveness and cost-effectiveness of intravenous formulations of topotecan monotherapy, pegylated liposomal doxorubicin hydorocholoride (PLDH) monotherapy and paclitaxel used alone or in combination with a platinum-based compound for the second-line or subsequent treatment of advanced ovarian cancer.
View All Related Papers

Articles

Inhibition of Nucleic Acid Synthesis by Antibiotics

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.

Applications of Graphene Oxide and Reduced Graphene Oxide

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.

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