Epirubicin HCl

Antibiotic antitumor agent CAS# 56390-09-1

Epirubicin HCl

Catalog No. BCC1192----Order now to get a substantial discount!

Product Name & Size Price Stock
Epirubicin HCl:5mg $43.00 In stock
Epirubicin HCl:10mg $73.00 In stock
Epirubicin HCl:25mg $172.00 In stock
Epirubicin HCl:50mg $301.00 In stock
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Chemical structure

Epirubicin HCl

3D structure

Chemical Properties of Epirubicin HCl

Cas No. 56390-09-1 SDF Download SDF
PubChem ID 21584061 Appearance Powder
Formula C27H30ClNO11 M.Wt 579.98
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 4'-Epidoxorubicin,Epirubicin hydrochloride
Solubility DMSO : ≥ 103.3 mg/mL (178.11 mM)
H2O : 50 mg/mL (86.21 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride
SMILES [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(=O)CO.[H+]
Standard InChIKey MWWSFMDVAYGXBV-FGBJBKNOSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Epirubicin HCl

DescriptionAntibiotic antitumor agent. Inhibits the synthesis and function of DNA (IC50 = 62.7 μM in rat glioblastoma cell lines) and inhibits the relaxing property of topoisomerase II.

Protocol

Cell Assay [3]
Hep G2 cells (500 cells/well, monolayer) are plated in a 96-well plate. The next day the cells are treated with Epirubicin in the medium. At the end of the incubation periods, 15% volume of MTT dye solution is added. After 1 hr of incubation at 37°C, an equal volume of solubilization/stop solution (dimethylsul-foxide) is added to each well for an additional 1 hr incubation. The absorbance of the reaction solution at 570 nm is recorded.

References:
[1]. Cersosimo RJ, et al. 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]. Ozkan, A., et al. Epirubicin HCl toxicity in human-liver derived hepatoma G2 cells. Pol J Pharmacol, 2004. 56(4): p. 435-44. [3]. Bonadonna, G., et al. Drugs ten years later: epirubicin. Ann Oncol, 1993. 4(5): p. 359-69. [4]. Asanuma, F., et al. Antitumor activity of paclitaxel and epirubicin in human breast carcinoma, R-27. Folia Microbiol (Praha), 1998. 43(5): p. 473-4.

Epirubicin HCl Dilution Calculator

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Epirubicin HCl Molarity Calculator

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Preparing Stock Solutions of Epirubicin HCl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7242 mL 8.621 mL 17.242 mL 34.4839 mL 43.1049 mL
5 mM 0.3448 mL 1.7242 mL 3.4484 mL 6.8968 mL 8.621 mL
10 mM 0.1724 mL 0.8621 mL 1.7242 mL 3.4484 mL 4.3105 mL
50 mM 0.0345 mL 0.1724 mL 0.3448 mL 0.6897 mL 0.8621 mL
100 mM 0.0172 mL 0.0862 mL 0.1724 mL 0.3448 mL 0.431 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Epirubicin HCl

Epirubicin is an inhibitor of DNA topoisomerase (TOPII) [1].

Epirubicin belongs to the Anthracylines chemical class, it is a sort of DNA topoisomerase poison. It can inhibit the religation step of DNA topology, resulting in stabilization of the 5’ phosphotyrosyl-DNA complex (cleavage complex). These lesions are cytotoxic and lead to activation of the DNA damage response and potentially apoptosis. Because of this, it is usually used in cancer therapy. Unfortunately, it also has genotoxic side effects, including the formation of leukemogenic chromosome translocations [1].

Epirubicin is one of the chemotherapeutic agents used for the treatment of Osteosarcoma. It exhibits growth inhibition of tumors by inducing apoptosis. Conversely, it reduces apoptosis in OS cells by activating NF-κB. It is reported that epirubicin combined with cerulenin can enhance the anti-tumor activity in vitro and in vivo [2].

References:
[1] Ian G. Cowell, Caroline A. Austin. Mechanism of Generation of Therapy Related Leukemia in Response to Anti-Topoisomerase II Agents. International Journal of Environmental Research and Public Health. 2012 (9): 2075-2091.
[2] Z.L. LIU, G. WANG, Y. SHU, P.A. ZOU, Y. ZHOU and Q.S. YIN. Enhanced antitumor activity of epirubicin combined with cerulenin in osteosarcoma. Molecular Medicine Reports. 2012 (5): 326-330.

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References on Epirubicin HCl

Epirubicin HCl toxicity in human-liver derived hepatoma G2 cells.[Pubmed:15520498]

Pol J Pharmacol. 2004 Jul-Aug;56(4):435-44.

Epirubicin HCl is a new anthracycline analog and derivative of doxorubicin. Doxorubicin is a potent anticancer agent, the use of which is limited by its cumulative dose-dependent cardiotoxicity. Epirubicin HCl has more favorable therapeutic index than doxorubicin and possesses less hematologic and cardiac toxicity at comparable doses. Hepatoma G2 cells are a valuable model to study hepatocellular carcinoma and the liver, where drugs are metabolized. The goal of our study was to evaluate the cytotoxic effect of Epirubicin HCl on viability of Hep G2 cells measured using the MTT cytotoxicity test. Epirubicin HCl produced a concentration- and time-dependent cytotoxicity to Hep G2 cells. The mechanism of cytotoxicity of Epirubicin HCl (IC(50) value of 1.6 mug/ml within 24 h) appeared to involve a production of free radical species since activities of free radical scavenging enzymes (SOD, catalase, Se-dependent GPx) were increased. Addition of SOD prevented cytotoxicity of Epirubicin HCl, and also counteracted the apoptosis. DNA fragmentation was determined to evaluate apoptosis. Western blot analysis indicated a decrease in GST-pi expression and increased activity of NADPH-dependent cytochrome P450 reductase which is a major enzyme in the conversion of Epirubicin HCl to a free radical. It is proposed that production of reactive oxygen species increased by the treatment with Epirubicin HCl can cause lipid peroxidation, which subsequently promotes apoptosis and reduces cell viability. Superoxide dismutase, catalase and glutathione peroxidase must be considered as a part of the intracellular antioxidant defense mechanism of Hep G2 cells against single electron reducing quinone-containing anticancer antibiotics.

Palonosetron HCl compatibility and stability with doxorubicin HCl and epirubicin HCl during simulated Y-site administration.[Pubmed:15613463]

Ann Pharmacother. 2005 Feb;39(2):280-3.

BACKGROUND: Palonosetron HCl is a selective 5-HT3 receptor antagonist used for the prevention of chemotherapy-induced nausea and vomiting. Palonosetron HCl may be administered with other drugs by Y-site administration, including doxorubicin HCI and epirubicin HCI. Consequently, stability and compatability information are needed to verify the acceptability of such Y-site administration. OBJECTIVE: To evaluate the physical and chemical stability of undiluted palonosetron HCl 50 microg/mL with doxorubicin HCl 1 mg/mL and Epirubicin HCl 0.5 mg/mL during simulated Y-site administration. METHODS: Triplicate samples of palonosetron HCl with each of the anthracycline chemotherapy drugs were tested. Samples were stored and evaluated for up to 4 hours at room temperature near 23 degrees C. Physical stability was assessed using turbidimetric and particulate measurement, as well as visual inspection. Chemical stability was assessed by HPLC. RESULTS: All of the admixtures were clear and red-orange when viewed in normal fluorescent room light and with a Tyndall beam. Measured turbidity and particulate content were low initially and remained low throughout the study. The drug concentration was unchanged in any of the samples throughout the study. CONCLUSIONS: Palonosetron HCl is physically and chemically stable with doxorubicin HCl and Epirubicin HCl during simulated Y-site administration of these drugs over 4 hours at ambient room temperature.

Spectrophotometric investigation of the chemical compatibility of the anticancer drugs irinotecan-HCl and epirubicin-HCl in the same infusion solution.[Pubmed:15947932]

Cancer Chemother Pharmacol. 2005 Nov;56(5):529-34.

The use of infusional chemotherapy, especially in an ambulatory setting, absolutely requires that the individual agents remain stable in solution at room temperature and that the drugs be compatible. Because of this, investigation of the chemical compatibilities of chemotherapeutic drug combinations given in the same infusion solution is quite important especially if the drugs are to remain in solution for long periods. Thus, the visual and chemical compatibility of irinotecan and epirubicin in the same infusion solution were investigated using both reference standards and pharmaceutical dosage forms. No sign of incompatibility was observed upon visual examination by means of effervescence, pH change, precipitation and colour change. But a chemical incompatibility was observed using a spectrophotometric method in the spectra of irinotecan-HCl and epirubicin-HCl. The molar ratio of epirubicin-HCl/irinotecan-HCl at which the interaction reached a maximum was found to be 2:1. The chemical interaction occurred immediately after admixing and no visual or spectral change was noticed for 24 h after the interaction had occurred. It is concluded that these drugs are chemically incompatible. While the applicability of these two drugs in combination is investigated in further pharmacological studies, their chemical interaction should also be a consideration. The positive or negative contribution of this interaction to the pharmacological effect of the combination might be of importance, and therefore should be investigated in further clinical trials.

Surface-modified Epirubicin-HCl liposomes and its in vitro assessment in breast cancer cell-line: MCF-7.[Pubmed:25586675]

Drug Deliv. 2016 May;23(4):1152-62.

BACKGROUND: Epirubicin-HCl is highly efficient for breast cancer management at a concentration of 60-90 mg/m(2). However, its application is limited due to cumulative dose-dependent cardio-toxicity. PURPOSE: The main aim of this study was to formulate breast cancer-targeted liposomal carrier by surface conjugation of transferrin to minimize cardio-toxicity of drug along with improved pharmacokinetic profile. METHOD: Liposomes were formulated by ethanol injection method using HSPC, cholesterol and DSPG and later loaded with drug by the ammonium sulfate gradient method. The formulation was characterized for physicochemical properties like size, zeta potential, entrapment efficiency, TEM; in vitro tests like electro-flocculation, hemolysis and drug release; cell line study (MCF-7 cells); in vivo studies including LD50 determination, pharmacokinetic analysis, myocardial toxicity determination and stability. RESULTS AND DISCUSSION: Optimized formulation had molar ratio of 60:30:8:2 (HSPC:Chol:DSPG:mPEG-DSPE) with entrapment efficiency approximately 83%, particle size below 200 nm and zeta potential about -20 mV. In vitro studies proved non-interfering property and drug release character of formulation while cell line studies demonstrated improvement in cell uptake and thereby increased cytotoxicity of targeted formulation. The IC50 value obtained for epirubicin solution, non-targeted and targeted liposomes was 0.675, 0.532 and 0.192 microg/ml, respectively. Furthermore, in vivo tests validated safety and distribution profile of prepared formulations. CONCLUSION: Apt properties of prepared Epirubicin-HCl liposomal formulation warrant its clinical application in breast cancer treatment after further studies.

Comparative activity of anthracycline 13-dihydrometabolites against rat glioblastoma cells in culture.[Pubmed:2597184]

Biochem Pharmacol. 1989 Nov 15;38(22):4069-74.

We have studied the growth inhibition, DNA synthesis inhibition and cell incorporation of five 13-dihydrometabolites of anthracyclines in a model of doxorubicin-sensitive and -resistant rat C6 glioblastoma cells. These compounds were major metabolites for doxorubicin, epirubicin, daunorubicin, idarubicin and the new anthracycline 4'-deoxy-4'-iododoxorubicin and are known to be present in appreciable amounts in the plasma of patients treated with these drugs. We have shown that in vitro growth inhibition in sensitive cells was either much lower than that of the parent drug (doxorubicinol, epirubicinol, daunorubicinol), or similar to it (idarubicinol, 4'-iodoxorubicinol). In resistant cells, growth inhibition was about 100 times lower than in wild cells, and was always lower than that of the parent anthracycline. DNA synthesis inhibition occurred in sensitive cells for doses about 100 times higher than those required for growth inhibition, but in resistant cells, similar doses provided growth inhibition and DNA synthesis inhibition. Metabolite incorporation was always lower than that of the corresponding parent anthracycline; it was greatly reduced in resistant cells as compared to sensitive ones. The calculated intracellular concentrations obtained for the same growth inhibition are higher in resistant cells than in sensitive cells; in contrast, the calculated intracellular concentrations obtained for the same DNA synthesis inhibition are similar in resistant and sensitive cells, and similar for all the metabolites studied. These results suggest that the amount of drug incorporated is primarily responsible for DNA synthesis inhibition, which is directly correlated to growth inhibition in resistant cells, but not in sensitive cells.

DNA polymerases and DNA topoisomerases as targets for the development of anticancer drugs.[Pubmed:3026237]

Anticancer Res. 1986 Sep-Oct;6(5):935-40.

Studies of a variety of compounds designed as derivatives of prototype active molecules aphidicolin and doxorubicin are reported. So far none of the aphidicolin simpler analogues is as active as the parental molecule. Ten anthracycline analogues, characterized for their cytotoxicity, antitumor activity and inhibition of the relaxing activity of purified human DNA topoisomerase II can be divided into five groups. The majority of the tested compounds shows properties very similar to those of doxorubicin. Epirubicin shows extremely high inhibitory activity toward the relaxing property of topoisomerase II but its antitumor activity and cytotoxicity are similar to those of the former group. The third group includes a compound with extremely high cytotoxicity. The fourth group is represented by a compound which shows a cytotoxicity. The fourth group is represented by a compound which shows a cytotoxicity. The fourth group is represented by a compound which shows a cytotoxicity typical of anthracyclines and good antitumor activity but which has no specific inhibitory activity on topoisomerase II. A fifth group includes a totally inactive compound. Our results suggest that the inhibition of human DNA topoisomerase II is only partially correlated with antitumor activity.

Description

Epirubicin hydrochloride (4'-Epidoxorubicin hydrochloride), a semisynthetic L-arabino derivative of doxorubicin, has an antineoplastic agent by inhibiting Topoisomerase. Epirubicin hydrochloride is a Forkhead box protein p3 (Foxp3) inhibitor and inhibits regulatory T cell activity.

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