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  • 44583 - Doxorubicin hydrochloride

44583 Sigma-Aldrich

Doxorubicin hydrochloride

suitable for fluorescence, 98.0-102.0% (HPLC)

Synonym: DOX, Hydroxydaunorubicin hydrochloride

  • CAS Number 25316-40-9

  • Empirical Formula (Hill Notation) C27H29NO11 · HCl

  • Molecular Weight 579.98

  •  Beilstein/REAXYS Number 4229251

  •  EC Number 246-818-3

  •  MDL number MFCD00077757

  •  PubChem Substance ID 57650234



Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Application, Antibiotics by Mechanism of Action, Antibiotics  A-F,
Quality Level   200
biological source   synthetic
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   λex 470 nm; λem 585 nm in ethanol
suitability   suitable for fluorescence
Mode of action   DNA synthesis | interferes
  enzyme | inhibits
antibiotic activity spectrum   neoplastics
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
Gene Information   human ... TOP2A(7153)


General description

Chemical structure: tetracycline


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


1, 10, 50 mg in glass bottle

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 .


Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

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

Safety & Documentation

Safety Information

Signal word 
Hazard statements 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
What is the function of Doxorubicin hydrochloride, Product 44583?
In chemotherapy: "Doxorubicin HCl is the hydrochloride salt of doxorubicin, an anthracycline antibiotic with antineoplastic activity. Doxorubicin, isolated from the bacterium Streptomyces peucetius var. caesius, is the hydroxylated congener of daunorubicin."-National Cancer Institute.
At what concentration can Doxorubicin hydrochloride, Product 44583, be dissolved in water? At what concentration in DMSO?
The solubility of Product No. 44583 tested in water (50 mg/mL), yielding a clear orange to red solution.It is also soluble in DMSO (50 mg/mL), ethanol, methanol and tetrahydrofuran.
How stable is a solution of Doxorubicin hydrochloride, Product 44583?
According to the 11th edition of the chemicals encyclopedia published by the Royal Society of Chemistry, "aqueous solutions are unchanged after one month at 5 °C but unstable at higher temperatures or at either acid or alkaline pH.Several studies cite that stability is related to pH, exposure to light and the medium used for storage. Doxorubicin hydrochloride is subject to light degradation at <0.5 mg/mL, with considerable loss of bioactivity. If stored at 25 °C in the dark in 5% glucose, pH 4.7 (or 3.3% glucose + 0.3% sodium chloride, pH 4.4), solutions were stable (5% or less change) for at least 4 weeks."
How should I use Product D1515 - Doxorubicin hydrochloride to induce double strand breaks in the DNA of HeLa cells?
We do not test Product D1515 - Doxorubicin hydrochloride for biological activity with HELA cells.The following paper used 100 nM to 250 nM doxorubicin Adam Hermawan,et al., Journal of Natural Remedies, Vol. 12/2 (2012) 108-114The following paper uses 0.01 to 1.0 mug/ml doxorubicin SH Kim, et al., CANCER RESEARCH 32, 323-325, February 1972
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