Epirubicin HCl

Alias: 4'-epidoxorubicin HCl; 4'-Epidoxorubicin hydrochloride; IMI28; 4-epi DX; EPI; epi DX; 4-epiadriamycin; 4-epidoxorubicin; 4-epidoxorubicin HCl; epiADR; epidoxorubicin; epidorubicin; IMI 28; IMI-28; brand name: Ellence; Pharmorubicin PFS
Cat No.:V1395 Purity: ≥98%
Epirubicin HCl (formerly 4'-epidoxorubicin; epiADR; epidoxorubicin; IMI 28; IMI-28; Ellence; Pharmorubicin PFS), the hydrochloride salt of the 4'-epi-isomer of the anthracycline antineoplastic antibiotic doxorubicin, is a new anthracycline analog and a semisynthetic L-arabino derivative of doxorubicin approved as an anticancer medication.
Epirubicin HCl Chemical Structure CAS No.: 56390-09-1
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
250mg
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%

Product Description

Epirubicin HCl (formerly 4'-epidoxorubicin; epiADR; epidoxorubicin; IMI 28; IMI-28; Ellence; Pharmorubicin PFS), the hydrochloride salt of the 4'-epi-isomer of the anthracycline antineoplastic antibiotic doxorubicin, is a new anthracycline analog and a semisynthetic L-arabino derivative of doxorubicin approved as an anticancer medication. Doxorubicin is a powerful anticancer drug, but its cumulative dose-dependent cardiotoxicity limits its application. Compared to doxorubicin, epirubicin HCl has a better therapeutic index and, at equivalent doses, is less toxic to the heart and blood vessels. Antineoplastic agent epirubicin HCl works by preventing Topoisomerase from doing its job. By intercalating into DNA and interacting with topoisomerase II, epirubicin prevents RNA and protein synthesis as well as DNA replication and repair. In addition, this agent interacts with the lipids in cell membranes to produce toxic free-radical intermediates and lipid peroxidation.

Biological Activity I Assay Protocols (From Reference)
Targets
Topoisomerase
ln Vitro

Epirubicin hydrochloride (4'-Epidoxorubicin hydrochloride), like doxorubicin, interferes with the synthesis of DNA, RNA, and proteins and damages DNA as a means of achieving its antitumor effects. The integrity and functionality of cellular membranes may also be impacted by epirubicin hydrochloride. Epirubicin hydrochloride maximally kills cells during the S phase of the cell cycle. Effects are also observed in the early G2, G1, and M phases at higher concentrations[1].
Epirubicin hydrochloride exhibit antitumor activity against the majority of cancerous cells. With an IC50 of 1.6 μg/mL after 24 hours, epirubicin hydrochloride is cytotoxic to Hepatoma G2 cells. 1.6 μg/mL Hep G2 cells undergo apoptosis when exposed to epirubicin hydrochloride, which also increases catalase activity by 50%, serine-dependent glutathione peroxidase activity by 110%, and the activity of Cu, Zn-superoxide dismutase by 172% and Mn-superoxide dismutase by 135%. NADPH-CYP 450 reductase is expressed more in cells when epirubicin hydrochloride is present, whereas GST-π expression is decreased[3].

ln Vivo
Epirubicin hydrochloride (4'-Epidoxorubicin hydrochloride) exhibits clinical efficacy against a diverse array of tumor types, such as gastrointestinal cancer, head and neck cancer, ovarian cancer, prostatic carcinoma, transitional bladder carcinoma, breast cancer, malignant lymphomas, soft tissue sarcomas, lung cancer, pleural mesothelioma, and so forth[4].
Epirubicin hydrochloride reduces the tumor mass of the human breast tumor xenograft R-27 by 74.4% when given at a dose of 3.5 mg/kg[5].
Cell Assay
A 96-well plate is plated with 500 monolayer Hep G2 cells per well. The following day, epirubicin is added to the medium and the cells are treated. 15% volume of MTT dye solution is added at the conclusion of the incubation times. An equal volume of solubilization/stop solution (dimethylsulfoxide) is added to each well for an additional hour of incubation at 37°C after the first hour of incubation. At 570 nm, the reaction solution's absorbance is measured.
Animal Protocol
Dissolved in saline; 3.5 mg/kg; i.v. injection
Human breast tumor xenograft R-27
References

[1]. Epirubicin: a review of the pharmacology, clinical activity, and adverse effects of an adriamycin analogue. J Clin Oncol. 1986 Mar;4(3):425-39.

[2]. Epirubicin, Identified Using a Novel Luciferase Reporter Assay for Foxp3 Inhibitors, Inhibits Regulatory T Cell Activity. PLoS One. 2016 Jun 10;11(6):e0156643.

[3]. Epirubicin HCl toxicity in human-liver derived hepatoma G2 cells. Pol J Pharmacol, 2004. 56(4): p. 435-44.

[4]. Drugs ten years later: epirubicin. Ann Oncol, 1993. 4(5): p. 359-69.

[5]. Antitumor activity of paclitaxel and epirubicin in human breast carcinoma, R-27. Folia Microbiol (Praha), 1998. 43(5): p. 473-4.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H30CLNO11.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 #
56390-09-1
Related CAS #
56390-09-1(HCl salt); 56420-45-2
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-FGBSZODSSA-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,5R,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
4'-epidoxorubicin HCl; 4'-Epidoxorubicin hydrochloride; IMI28; 4-epi DX; EPI; epi DX; 4-epiadriamycin; 4-epidoxorubicin; 4-epidoxorubicin HCl; epiADR; epidoxorubicin; epidorubicin; IMI 28; IMI-28; brand name: Ellence; Pharmorubicin PFS
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: 25~100 mg/mL (43.1~172.4 mM)
Water: ~100 mg/mL (~172.4 mM)
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.31 mM) (saturation unknown) in 5% DMSO + 40% PEG300 + 5% Tween80 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.31 mM) (saturation unknown) in 5% DMSO + 95% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
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.

View More

Solubility in Formulation 3: ≥ 2.08 mg/mL (3.59 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.


Solubility in Formulation 4: ≥ 0.5 mg/mL (0.86 mM) (saturation unknown) in 1% DMSO 99% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 5: 1.1 mg/mL (1.90 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
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
NCT01779206 Active
Recruiting
Drug: Epirubicin
Drug: Docetaxel
Breast Cancer West German Study Group May 2012 Phase 2
Phase 3
NCT03356860 Active
Recruiting
Drug: Epirubicin
Drug: Paclitaxel
Breast Cancer
Luminal B
Grand Hôpital de Charleroi April 13, 2017 Phase 1
Phase 2
NCT04418154 Active
Recruiting
Drug: epirubicin hydrochloride
Drug: Toripalimab
Triple Negative Breast Cancer Fudan University June 9, 2020 Phase 2
NCT04172259 Active
Recruiting
Drug: Epirubicin
Drug: Docetaxel
Neoadjuvant Chemotherapy
Breast Cancer
Sun Yat-sen University January 10, 2019 Phase 2
NCT01340430 Active
Recruiting
Drug: Trastuzumab HER-2 Positive Breast Cancer Lucia Del Mastro,MD March 2011 Phase 2
Biological Data
  • Epirubicin (EPI) represses the inhibitory effect of Foxp3 on the activity of NF-κB. PLoS One . 2016 Jun 10;11(6):e0156643.
  • Epirubicin (EPI) blocks the physical interaction between Foxp3 and the p65 subunit of NF-κB. PLoS One . 2016 Jun 10;11(6):e0156643.
  • Epirubicin (EPI) inhibits the immunosuppressive activity of murine Tregs in vitro. PLoS One . 2016 Jun 10;11(6):e0156643.
Contact Us Back to top