Doxorubicin

Alias: Adriamycin; Hydroxydaunorubicin; ADR; DOX. Code name: FI106; chloridrato de doxorrubicina. Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex. Abbreviations: ADM; Adria;

Cat No.:V2644 Purity: ≥98%

COA Product Data Instructions for use SDS

Doxorubicin (Adriamycin; NSC-123127; FI-106; Adriblastine; Adrimedac) is a naturally occuring anthracycline antibiotic isolated from the bacterium Streptomyces peucetius var.

Doxorubicin Chemical Structure CAS No.: 23214-92-8
Product category: Topoisomerase

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Doxorubicin:

Doxorubicin HCl (adriamycin; NSC 123127)

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Doxorubicin (Adriamycin; NSC-123127; FI-106; Adriblastine; Adrimedac) is a naturally occuring anthracycline antibiotic isolated from the bacterium Streptomyces peucetius var. caesius with potent anticancer activity and was approved as an anticancer chemotherapeutic medication. This is an inhibitor of DNA topoisomerase II that can cause apoptosis and damage to DNA in tumor cells. Danunorubicin's hydroxylated congener is called doxorubicin. In order to stop DNA replication and ultimately stop protein synthesis, doxorubicin works by intercalating between base pairs in the DNA helix. Doxorubicin also inhibits the enzyme topoisomerase II.

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

In vitro activity: 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. The doxorubicin-resistant breast cancer cell line MCF7/Dx exhibits suppression of resistance upon pre-treatment with GSNO (nitrosoglutathione), which is accompanied by increased protein glutathionylation and doxorubicin accumulation in the nucleus. Elevated cyclin G2 (CycG2) expression and protein phosphorylation in the ATM, ATM, and Rad3-related (ATR) signaling pathways are responsible for doxorubicin-induced G2/M checkpoint arrest. In mouse embryonic fibroblasts (MEFs) and cardiomyocytes, doxorubicin inhibits AMP-activated protein kinase (AMPK), leading to SIRT1 dysfunction, p53 accumulation, and increased cell death. These effects can be further sensitized by pre-inhibition of AMPK. 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 administered in nanomolar doses to neuroblastoma cells, doxorubicin causes a dose-dependent over-ubiquitination of a particular set of proteins without any detectable proteasome inhibition. It also 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.

ln Vivo

The most effective method for reducing the size of MB231 tumors and extending the survival of mice in vivo is to combine doxorubicin with adenoviral MnSOD (AdMnSOD) and 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU). Doxorubicin is indispensable in the treatment of solid tumors in childhood, soft tissue sarcomas, osteosarcomas, Kaposi's sarcoma, oesophageal carcinomas, Hodgkin and non-Hodgkin lymphomas, and solid tumors of the breast and esophagus. However, its use is restricted by the toxic side effects, both acute and chronic.

Cell Assay

Three 96-well U-bottom microplates with a suspension of Hela cells (3×10⁴ cell/mL) dispensed in 160 μL are then incubated for 24 hours at 37°C in a fully humidified atmosphere with 5% CO₂. In plate 1, 200 μL of final volume is filled with serial dilutions of doxorubicin (20 μL; final concentration, 0.1-2 μM) and simvastatin (20 μL; final concentration, 0.25-2 μM) before an additional 72 hours of incubation. 40 μL of each drug's serial dilution—doxorubicin or simvastatin—are added to plates 2 and 3. The medium is aspirated and the cells are cleaned in PBS after a 24-hour incubation period. Then, to reach a final volume of 200 μL, serial dilutions of the other medication (40 μL) are added, and the mixture is incubated for 48 hours. Separate positive controls (40 μL in each well) consisting of doxorubicin and simvastatin are employed, while the negative controls consist solely of solvent-treated cells. A 20 μL MTT solution (5 mg/mL in PBS) is added to each well, and the cells are incubated for three hours in order to assess cell survival. Afterwards, 150 μL of DMSO is added to the medium, and the solution is pipetted repeatedly to completely dissolve the formazan crystals. In the next step, an ELISA plate reader measures absorbance at 540 nm. Three assays are conducted, one for each drug concentration, using four or eight wells. Doxorubicin's cytotoxic/cytostatic effect is quantified and expressed as relative viability (% control). It is assumed that 100% of the cells in the negative control will survive. * Relative viability = (background absorbance - experimental absorbance) / (background absorbance - absorbance of untreated controls)× 100%[4].

Animal Protocol

Mice: Three to four-week-old male athymic nude mice are used. Subcutaneous injection of PC3 cells (4×10⁶) is administered to mice via the flanks. When the volumes of the xenografts reached approximately 100 mm³, the animals with tumors were randomly assigned to treatment groups, with five or six mice per group. Digital calipers are used to measure tumors and the formula Volume=Width²×Length×0.52 is used to calculate the volume of the tumor, with width denoting its shorter dimensions. Therapy is given as prescribed with vehicle (PBS with 0.1% BSA), Doxorubicin (2–8 mg/kg), Apo2L/TRAIL (500 μg/animal), or a mix of 4 mg/kg Doxorubicin and 500 μg Apo2L/TRAIL. Doxorubicin is delivered systemically, while Apo2L/TRAIL is delivered intra-tumorally or systemically. Every therapy is administered just once. Every day, mice are observed for indications of negative consequences, such as lethargic behavior and disheveled look. Looks like the treatments were well received. Every data point has its mean±SEM computed. Student t-tests are used to analyze differences between treatment groups. When P is less than 0.05, differences are deemed significant. Rats: Thirty-year-old man A total of ten Doxorubicin schedules—Doxorubicin schedule 1 (n = ten), Doxorubicin schedule 2 (n = ten), and Doxorubicin schedule 3 (n = ten)—are randomly assigned to Sprague-Dawley rats weighing 250–300 g. 10 mg/kg is the total dose of doxorubicin for all treatment regimens. One intraperitoneal injection of doxorubicin (10 mg/kg) is administered as part of Schedule 1. Doxorubicin injections intraperitoneally (10 mg/kg) for ten days in a row are part of Schedule 2. Schedule 2 calls for ten intraperitoneal injections of doxorubicin (1 mg/kg) spaced ten days apart. Schedule 3 calls for five weeks of weekly intraperitoneal injections of doxorubicin at a dose of two milligrams per kilogram. As long as there are at least three rats in each group, blood pressure and cardiac function are measured in all surviving animals prior to the first Doxorubicin treatment and once a week after the start of Doxorubicin treatment.

References

[1]. Targeting DNA topoisomerase II in cancer chemotherapy.Nat Rev Cancer. 2009 May;9(5):338-50.

[2]. Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones. Bioorg Med Chem. 2007 Feb 15;15(4):1651-8.

[3]. Doxorubicin inhibits human DNA topoisomerase I. Cancer Chemother Pharmacol. 1992;30(2):123-5.

[4]. Cytotoxic evaluation of doxorubicin in combination with simvastatin against human cancer cells. Res Pharm Sci. 2010 Jul;5(2):127-33.

[5]. Doxorubicin increases the effectiveness of Apo2L/TRAIL for tumor growth inhibition of prostate cancerxenografts. BMC Cancer. 2005 Jan 7;5:2.

[6]. Doxorubicin cardiotoxicity in the rat: an in vivo characterization. J Am Assoc Lab Anim Sci. 2007 Jul;46(4):20-32.

[7]. Elimination of HIV-1 infection by treatment with a doxorubicin-conjugated anti-envelope antibody. AIDS. 2006;20(15):1911-1915.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C27H29NO11

Molecular Weight

543.52

Exact Mass

543.17

Elemental Analysis

C, 59.66; H, 5.38; N, 2.58; O, 32.38.

CAS #

23214-92-8

Related CAS #

25316-40-9 (HCl); 23214-92-8 (Doxorubicin free base)

Appearance

Deep-red to black 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

InChi Key

AOJJSUZBOXZQNB-TZSSRYMLSA-N

InChi Code

InChI=1S/C27H29NO11/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/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

Synonyms

Adriamycin; Hydroxydaunorubicin; ADR; DOX. Code name: FI106; chloridrato de doxorrubicina. Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex. Abbreviations: ADM; Adria;

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: 20~100 mg/mL (34.5~184 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)

Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

Oral Formulations

Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8399 mL	9.1993 mL	18.3986 mL
	5 mM	0.3680 mL	1.8399 mL	3.6797 mL
	10 mM	0.1840 mL	0.9199 mL	1.8399 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

Mass

Concentration

Volume

Molecular Weight*

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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
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See Example

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.

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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

Molecular formula

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g/mol

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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.

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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)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

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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.)

% DMSO

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% ddH₂O

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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.

Note： (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
NCT06069375	Active Recruiting	Drug: Caelyx®	Breast Cancer	European Institute of Oncology	March 25, 2016	Phase 2
NCT04032964	Active Recruiting	Drug: L19TNF Drug: DOXORUBICIN	Soft Tissue Sarcoma	Philogen S.p.A.	September 5, 2019	Phase 1
NCT01746238	Active Recruiting	Drug: Bevacizumab Drug: Doxorubicin	Sarcoma	Massachusetts General Hospital	March 2013	Phase 1
NCT01670500	Active Recruiting	Drug: Cyclophosphamide Drug: Doxorubicin	Breast Cancer	Beth Israel Deaconess Medical Center	October 2012	Phase 2
NCT05448820	Active Recruiting	Drug: Envafolimab Drug: Doxorubicin	Advanced Sarcoma Metastatic Sarcoma	Tracon Pharmaceuticals Inc.	November 14, 2022	Phase 1 Phase 2

Biological Data

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