Doxorubicin HCl (adriamycin; NSC 123127)

Alias: Adriamycin; Hydroxydaunorubicin hydrochloride; FI106; ADR; Doxo; Dox HCl; FI-106; FI 106; Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex
Cat No.:V1389 Purity: =99.49%
Doxorubicin HCl (formerly known as Adriamycin; FI 106; Adriblastina; DOXOCELL; Doxolem; NSC-123127 etc.) is an anthracycline antibiotic agent with anticancer activity.
Doxorubicin HCl (adriamycin; NSC 123127) Chemical Structure CAS No.: 25316-40-9
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
500mg
1g
Other Sizes
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text

 

  • Business Relationship with 5000+ Clients Globally
  • Major Universities, Research Institutions, Biotech & Pharma
  • Citations by Top Journals: Nature, Cell, Science, etc.
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Purity: =99.49%

Purity: =99.49%

Purity: ≥98%

Product Description

Doxorubicin HCl (formerly known as Adriamycin; FI 106; Adriblastina; DOXOCELL; Doxolem; NSC-123127 etc.) is an anthracycline antibiotic agent with anticancer activity. It causes DNA damage and apoptosis in tumor cells and inhibits DNA topoisomerase II. The use of it as an antineoplastic agent was authorized. Doxorubicin, the hydroxylated congener of daunorubicin, is isolated from Streptomyces peucetius var. caesius. By intercalating between base pairs in the DNA helix, doxorubicin inhibits the synthesis of proteins by preventing DNA replication. Furthermore, topoisomerase II is inhibited by doxorubicin.

Biological Activity I Assay Protocols (From Reference)
Targets
Topoisomerase I ( IC50 = 0.8 μM ); Topoisomerase II ( IC50 = 2.67 μM ); Daunorubicins/Doxorubicins; HIV-1
ln Vitro

Doxorubicin, an antibiotic anthracycline, is widely believed to exhibit its anti-tumor activity on two basic levels: it modifies DNA and generates free radicals to cause DNA damage that causes cancer cells to undergo apoptosis. Doxorubicin inhibits DNA topoisomerase II (TOP2) and can intercalate into DNA strands to prevent DNA synthesis. When cells are multiplying quickly and expressing a lot of TOP2, doxorubicin works best. Additionally, doxorubicin can cause apoptosis by releasing cytochrome c from the mitochondria, ceramide (which activates p53 or other downstream pathways like JNK), the degradation of Akt by serine threonine proteases, an increase in the production of FasL (death receptor Fas/CD95 ligand) mRNA, and an increase in free radical production.[2]
Pre-treatment with GSNO (nitrosoglutathione) results in increased protein glutathionylation and doxorubicin accumulation in the nucleus of the doxorubicin-resistant breast cancer cell line MCF7/Dx, which in turn suppresses resistance.[3]
Doxorubicin increased expression of cyclin G2 (CycG2) and phosphorylation of proteins in the ATM, ATM and Rad3-related (ATR) signaling pathways are responsible for induced G2/M checkpoint arrest.[5]
Doxorubicin inhibits AMP-activated protein kinase (AMPK), which can be further sensitized by pre-inhibition of AMPK. This results in SIRT1 dysfunction, p53 accumulation, and increased cell death in mouse embryonic fibroblasts (MEFs) and cardiomyocytes.[6]
Doxorubicin causes a noticeable heat shock response, and in neuroblastoma cells, it increases the apoptotic effect by either inhibiting or silencing heat shock proteins. When nanomolar Doxorubicin is administered to neuroblastoma cells, it results in a dose-dependent over-ubiquitination of a particular set of proteins without any detectable proteasome inhibition. Additionally, it causes a decrease in the activity of ubiquitinated enzymes like lactate dehydrogenase and α-enolase, whose protein ubiquitination patterns resemble those of the proteasome inhibitor Bortezomib, suggesting that Doxorubicin may also cause protein damage. [8]

ln Vivo
In vivo, the most effective combination for reducing the volumes of MB231 tumors and extending mouse survival is doxorubicin plus 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) in conjunction with adenoviral MnSOD (AdMnSOD).[1]
Doxorubicin is indispensable in the treatment of solid tumors in childhood, soft tissue sarcomas, Hodgkin and non-Hodgkin lymphomas, osteosarcomas, Kaposi's sarcoma, and breast and oesophageal carcinomas, despite the fact that its use is restricted by the toxic side effects, both acute and chronic.[2]
Cell Assay
Doxorubicin at varying concentrations was applied to parental ID8 or erastin-resistant ID8 cells for a duration of 24 hours.
Animal Protocol
Female athymic nude mice injected s.c. with MB231 cells; 3 mg/kg/day; Delivered intratumorly
Female athymic nude mice injected s.c. with MB231 cells
References

[1]. Cancer Res . 2009 May 15;69(10):4294-300.

[2]. Food Chem Toxicol . 2010 Jun;48(6):1425-38.

[3]. Biochem J . 2011 Dec 1;440(2):175-83.

[4]. Br J Cancer . 2011 Mar 15;104(6):957-67.

[5]. J Biol Chem . 2012 Jun 29;287(27):22838-53.

[6]. J Biol Chem . 2012 Mar 9;287(11):8001-12.

[1]. Clin Cancer Res . 2012 May 1;18(9):2638-47.

[2]. FEBS J . 2012 Jun;279(12):2182-91.

[3]. Nat Rev Cancer . 2009 May;9(5):338-50.

[4]. Bioorg Med Chem . 2007 Feb 15;15(4):1651-8.

[5]. Cancer Chemother Pharmacol . 1992;30(2):123-5.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H29NO11.HCL
Molecular Weight
579.98
Exact Mass
579.15
Elemental Analysis
C, 55.91; H, 5.21; Cl, 6.11; N, 2.42; O, 30.34
CAS #
25316-40-9
Appearance
Red solid powder
SMILES
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl
InChi Key
MWWSFMDVAYGXBV-RUELKSSGSA-N
InChi Code
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
Chemical Name
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Synonyms
Adriamycin; Hydroxydaunorubicin hydrochloride; FI106; ADR; Doxo; Dox HCl; FI-106; FI 106; Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 83.3~100 mg/mL (143.7~172.4 mM)

Water: 10~50 mg/mL; Dox HCl can be dissolved in water (1.Annals of Biological Research, 2012, 3,4414-4419; 2.Annal of Oncology 1999, 10, 391-395)

Ethanol: <1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7242 mL 8.6210 mL 17.2420 mL
5 mM 0.3448 mL 1.7242 mL 3.4484 mL
10 mM 0.1724 mL 0.8621 mL 1.7242 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03712956 Active
Recruiting
Drug: Caelyx® Breast Cancer European Institute of Oncology March 25, 2016 Phase 2
NCT04032964 Active
Recruiting
Drug: Doxorubicin
Drug: L19TNF
Soft Tissue Sarcoma Philogen S.p.A. September 5, 2019 Phase 1
NCT01746238 Active
Recruiting
Drug: Doxorubicin
Drug: Bevacizumab
Sarcoma Massachusetts General Hospital March 2013 Phase 1
NCT01840592 Active
Recruiting
Drug: Sorafenib
Drug: Doxorubicin
Hepatocellular Carcinoma Memorial Sloan Kettering Cancer
Center
April 2013 Phase 2
NCT02451943 Active
Recruiting
Drug: Doxorubicin
Drug: Placebo
Soft Tissue Sarcoma Eli Lilly and Company September 14, 2015 Phase 3
Biological Data

  • Doxorubicin (Adriamycin)
    AdMnSOD infection + BCNU sensitized cells to adriamycin and radiation.Cancer Res.2009 May 15;69(10):4294-300.

  • Doxorubicin (Adriamycin)
    AdMnSOD infection plus BCNU sensitized the antitumor effect of adriamycin in vivo and increased animal survival.Cancer Res.2009 May 15;69(10):4294-300.
Contact Us