MilliporeSigma
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D8809

Sigma-Aldrich

Daunorubicin hydrochloride

meets USP testing specifications

Synonym(s):
Daunomycin hydrochloride
Empirical Formula (Hill Notation):
C27H29NO10 · HCl
CAS Number:
Molecular Weight:
563.98
Beilstein:
4229221
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Agency

USP/NF
meets USP testing specifications

form

solid

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.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(C)=O

InChI

1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1

InChI key

GUGHGUXZJWAIAS-QQYBVWGSSA-N

Gene Information

human ... TOP2A(7153)

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Packaging

50 mg in poly bottle
1, 10 mg in glass bottle

Biochem/physiol Actions

Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent.
Naturally fluorescent anthracycline antibiotic, anticancer drug. Substrate for Pgp, MRP-1 and BCRP. 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. Daunorubicin is sequestered into lysosomes according to a pH partitioning type mechanism. Strong inhibitor of DNA and RNA synthesis.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

  1. 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.

  2. 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.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. 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. 

  5. What is this compound soluble in?

    Per Martindale The Extra Pharmacopoeia, 31st edition, p. 565-3 (1996), this compound is freely soluble in water and methyl alcohol.  It is slightly soluble in alcohol, very slightly soluble in chloroform, and practically insoluble in acetone.

  6. What factors affect the stability of Product No. D8809, Daunorubicin hydrochloride, in solution?

    Per Martindale The Extra Pharmacopoeia, 31st edition, p. 565-3 (1996), stability in solution appeared to be partly related to pH.  Daunorubicin was more stable as the pH of the mixture became more acidic, with the best stability in glucose injection solution (5%) with a pH of 4.5  Although daunorubicin solutions are degraded by light, the effect is reported not to be significant at concentrations of 500 ug/mL or above.  However, below this concentration, precautions should be taken to protect solutions from light, and storage should be in polyethylene or polypropylene containers to minimize adsorptive losses.   

  7. Does Product No. D8809, Daunorubicin hydrochloride, have an expiration date?

    Yes, each lot of this product will have an expiration date, and this date (month and year) can be found on the certificate of analysis for the lot.

  8. Does the assay information on the certificate of analysis for Product No. D8809, Daunorubicin hydrochloride, pertain to a "dry" or "as is" basis?

    The assay information on the certificate of analysis is for the product "as is".

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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The Journal of biological chemistry, 278(50), 50234-50239 (2003-10-03)
The sequestration of drugs away from cellular target sites into cytoplasmic organelles of multidrug-resistant (MDR) cancer cells has been recently shown to be a cause for ineffective drug therapy. This process is poorly understood despite the fact that it has
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