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MedKoo Cat#: 100971 | Name: Epirubicin free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Epirubicin is an anthracycline drug used for chemotherapy. It can be used in combination with other medications to treat breast cancer in patients who have had surgery to remove the tumor. Similarly to other anthracyclines, epirubicin acts by intercalating DNA strands. Intercalation results in complex formation which inhibits DNA and RNA synthesis. It also triggers DNA cleavage by topoisomerase II, resulting in mechanisms that lead to cell death. Binding to cell membranes and plasma proteins may be involved in the compound's cytotoxic effects. Epirubicin also generates free radicals that cause cell and DNA damage.

Chemical Structure

Epirubicin free base
Epirubicin free base
CAS#56420-45-2 (free base)

Theoretical Analysis

MedKoo Cat#: 100971

Name: Epirubicin free base

CAS#: 56420-45-2 (free base)

Chemical Formula: C27H29NO11

Exact Mass: 543.1741

Molecular Weight: 543.53

Elemental Analysis: C, 59.67; H, 5.38; N, 2.58; O, 32.38

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 550.00 Ready to ship
50mg USD 950.00 Ready to ship
100mg USD 1,650.00 Ready to ship
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Related CAS #
56420-45-2 (free base) 56390-09-1 (HCl)
Synonym
Epirubicin free base; IMI28; IMI 28; IMI-28; 4-epi DX; EPI; epi DX; 4-epiadriamycin; 4-epidoxorubicin; 4-epidoxorubicin HCl; epiADR; epidoxorubicin; epidorubicin; brand name: Ellence; Pharmorubicin PFS.
IUPAC/Chemical Name
(8S,10S)-10-(((2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChi Key
AOJJSUZBOXZQNB-VTZDEGQISA-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
SMILES Code
O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@@H](O)[C@H](C)O4)=C3C(O)=C2C(C5=C1C=CC=C5OC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
This product was not soluble in common used solvents. It has low solubility (2 mg/mL with aid of ultrasonicate) in Ethanol plus chloroform (1:1, v/v)
Shelf Life
>3 years if stored properly
Drug Formulation
To be determined.
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Epirubicin is an antineoplastic agent by inhibiting Topoisomerase.
In vitro activity:
Intact red blood cells (RBC), human erythrocyte membranes and molecular models were used to gain insight on the toxic effects of epirubicin. Epirubicin induced structural perturbations in multilayers of DMPC (dimyristoylphosphatidylcholine). Epirubicin also disturbed the thermotropic behavior of both DMPC and DMPE (dimyristoylphosphatidylethanolamine) vesicles, whereas fluorescence spectroscopy demonstrated alterations in the fluidity of DMPC vesicles and the erythrocyte membrane. Furthermore, epirubicin changed the normal discoid form of RBC to echinocytes and stomatocytes. Finally, epirubicin induced conformational changes in the erythrocyte membrane proteins. These findings demonstrate that epirubicin interacts with lipids and proteins of the human erythrocyte membrane, effects that might compromise the integrity and function of cell membranes. Reference: Toxicol In Vitro. 2020 Oct;68:104964. https://www.sciencedirect.com/science/article/abs/pii/S0887233320305142?via%3Dihub
In vivo activity:
In vivo, epirubicin treatment of mice resulted in persistent reduction in lung vascular density and significantly increased infiltration of myeloid cells. These results suggest that modulation of endothelial status and inflammatory tissue microenvironment observed in response to low doses of epirubicin may predict risk for long-term secondary pathologies associated with chemotherapy. Reference: Front Cell Dev Biol. 2020 Aug 19;8:799. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7466755/

Preparing Stock Solutions

The following data is based on the product molecular weight 543.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Petit K, Suwalsky M, Colina JR, Contreras D, Aguilar LF, Jemiola-Rzeminska M, Strzalka K. Toxic effects of the anticancer drug epirubicin in vitro assayed in human erythrocytes. Toxicol In Vitro. 2020 Oct;68:104964. doi: 10.1016/j.tiv.2020.104964. Epub 2020 Aug 13. PMID: 32800948. 2. Eakin AJ, Mc Erlain T, Burke A, Eaton A, Tipping N, Allocca G, Branco CM. Circulating Levels of Epirubicin Cause Endothelial Senescence While Compromising Metabolic Activity and Vascular Function. Front Cell Dev Biol. 2020 Aug 19;8:799. doi: 10.3389/fcell.2020.00799. PMID: 32974345; PMCID: PMC7466755.
In vitro protocol:
1. Petit K, Suwalsky M, Colina JR, Contreras D, Aguilar LF, Jemiola-Rzeminska M, Strzalka K. Toxic effects of the anticancer drug epirubicin in vitro assayed in human erythrocytes. Toxicol In Vitro. 2020 Oct;68:104964. doi: 10.1016/j.tiv.2020.104964. Epub 2020 Aug 13. PMID: 32800948.
In vivo protocol:
1. Eakin AJ, Mc Erlain T, Burke A, Eaton A, Tipping N, Allocca G, Branco CM. Circulating Levels of Epirubicin Cause Endothelial Senescence While Compromising Metabolic Activity and Vascular Function. Front Cell Dev Biol. 2020 Aug 19;8:799. doi: 10.3389/fcell.2020.00799. PMID: 32974345; PMCID: PMC7466755.
1: Bi L, Zhang H, Han R, Chen W, Zhao N. Application of a combination of echocardiographic techniques in an experimental model of epirubicin-induced cardiotoxicity. Int J Cardiovasc Imaging. 2020 Feb 7. doi: 10.1007/s10554-020-01777-w. [Epub ahead of print] PubMed PMID: 32034566. 2: Ansari L, Derakhshi M, Bagheri E, Shahtahmassebi N, Malaekeh-Nikouei B. Folate conjugation improved uptake and targeting of porous hydroxyapatite nanoparticles containing epirubicin to cancer cells. Pharm Dev Technol. 2020 Feb 6:1-9. doi: 10.1080/10837450.2020.1725045. [Epub ahead of print] PubMed PMID: 32026739. 3: Kluger N, Jacot W, Frouin E, Rigau V, Poujol S, Dereure O, Guillot B, Romieu G, Bessis D. Permanent scalp alopecia related to breast cancer chemotherapy by sequential fluorouracil/epirubicin/cyclophosphamide (FEC) and docetaxel: a prospective study of 20 patients. Ann Oncol. 2012 Nov;23(11):2879-2884. doi: 10.1093/annonc/mds095. Epub 2019 Dec 4. PubMed PMID: 32018742. 4: Kitagawa K, Kawada K, Morita S, Inada M, Mitsuma A, Sawaki M, Iino S, Inden Y, Murohara T, Imai T, Ando Y. Prospective evaluation of corrected QT intervals and arrhythmias after exposure to epirubicin, cyclophosphamide, and 5-fluorouracil in women with breast cancer. Ann Oncol. 2012 Mar;23(3):743-747. doi: 10.1093/annonc/mdr296. Epub 2019 Dec 4. PubMed PMID: 32018670. 5: Vici P, Brandi M, Giotta F, Foggi P, Schittulli F, Di Lauro L, Gebbia N, Massidda B, Filippelli G, Giannarelli D, Di Benedetto A, Mottolese M, Colucci G, Lopez M. A multicenter phase III prospective randomized trial of high-dose epirubicin in combination with cyclophosphamide (EC) versus docetaxel followed by EC in node-positive breast cancer. GOIM (Gruppo Oncologico Italia Meridionale) 9902 study. Ann Oncol. 2012 May;23(5):1121-1129. doi: 10.1093/annonc/mdr412. Epub 2019 Dec 4. PubMed PMID: 32018566. 6: Ueno A, Yamaguchi K, Sudo M, Imai S. Sarcopenia as a risk factor of severe laboratory adverse events in breast cancer patients receiving perioperative epirubicin plus cyclophosphamide therapy. Support Care Cancer. 2020 Jan 3. doi: 10.1007/s00520-019-05279-x. [Epub ahead of print] PubMed PMID: 31900607. 7: Munker S, Vogelhuber M, Bornschein J, Stroszczynski C, Evert M, Schlitt H, Herr W, Teufel A. EpiCO (epirubicin, cyclophosphamide and vincristine) as treatment for extrapulmonary high-grade neuroendocrine neoplasms. Z Gastroenterol. 2020 Jan 2. doi: 10.1055/a-1042-6504. [Epub ahead of print] PubMed PMID: 31896137. 8: Lu J, Xue Y, Shen F, Gu H, Liu H, Hou J, Miao H. Transurethral holmium laser resection and transurethral electrocision combined with intravesical epirubicin within 24 hours postoperatively for treatment of bladder cancer. J Int Med Res. 2019 Dec 29:300060519887267. doi: 10.1177/0300060519887267. [Epub ahead of print] PubMed PMID: 31885339. 9: Huang L, Wang X, Zhou L, Di L, Zheng H, Jiang Z, Wang Y, Song X, Feng J, Yu S, Liu Y, Zheng H, Shen K, Tong Z, Shao Z. Oral vinorelbine versus intravenous vinorelbine, in combination with epirubicin as first-line chemotherapy in Chinese patients with metastatic breast cancer. Cancer Chemother Pharmacol. 2020 Jan;85(1):205-215. doi: 10.1007/s00280-019-04000-3. Epub 2019 Dec 14. PubMed PMID: 31838561. 10: Treder N, Maliszewska O, Olędzka I, Kowalski P, Miękus N, Bączek T, Bień E, Krawczyk MA, Adamkiewicz-Drożynska E, Plenis A. Development and validation of a high-performance liquid chromatographic method with a fluorescence detector for the analysis of epirubicin in human urine and plasma, and its application in drug monitoring. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Jan 1;1136:121910. doi: 10.1016/j.jchromb.2019.121910. Epub 2019 Nov 30. PubMed PMID: 31830661. 11: Peng J, Wang Z, Li Y, Lv D, Zhao X, Gao J, Teng H. Identification of differential gene expression related to epirubicin-induced cardiomyopathy in breast cancer patients. Hum Exp Toxicol. 2019 Dec 11:960327119893415. doi: 10.1177/0960327119893415. [Epub ahead of print] PubMed PMID: 31823667. 12: Perveen K, Masood F, Hameed A. Preparation, characterization and evaluation of antibacterial properties of epirubicin loaded PHB and PHBV nanoparticles. Int J Biol Macromol. 2020 Feb 1;144:259-266. doi: 10.1016/j.ijbiomac.2019.12.049. Epub 2019 Dec 7. PubMed PMID: 31821825. 13: Jandaghi N, Jahani S, Foroughi MM, Kazemipour M, Ansari M. Cerium-doped flower-shaped ZnO nano-crystallites as a sensing component for simultaneous electrochemical determination of epirubicin and methotrexate. Mikrochim Acta. 2019 Dec 5;187(1):24. doi: 10.1007/s00604-019-4016-2. PubMed PMID: 31807919. 14: Mo J, Shen L, Xu Q, Zeng J, Sha J, Hu T, Bi K, Chen Y. An Nd(3+)-Sensitized Upconversion Fluorescent Sensor for Epirubicin Detection. Nanomaterials (Basel). 2019 Nov 28;9(12). pii: E1700. doi: 10.3390/nano9121700. PubMed PMID: 31795129; PubMed Central PMCID: PMC6955805. 15: Kong L, Cai FY, Yao XM, Jing M, Fu M, Liu JJ, He SY, Zhang L, Liu XZ, Ju RJ, Li XT. RPV-modified epirubicin and dioscin co-delivery liposomes suppress non-small cell lung cancer growth by limiting nutrition supply. Cancer Sci. 2020 Feb;111(2):621-636. doi: 10.1111/cas.14256. Epub 2020 Jan 18. PubMed PMID: 31777993. 16: Yokoyama T, Makino H, Seki N, Ueda J, Hosone M, Katayama H, Takei H, Yoshida H. Neoadjuvant chemotherapy of capecitabine + epirubicin + cyclophosphamide combination therapy ( 'CEX' therapy) for HER-2 negative breast cancer, as retrospective study in our institute. J Nippon Med Sch. 2019 Nov 28. doi: 10.1272/jnms.JNMS.2020_87-204. [Epub ahead of print] PubMed PMID: 31776320. 17: Wang N, Li H, Zhu Y, Li N, Chen ZJ, Zhang C. Melatonin protects against Epirubicin-induced ovarian damage. J Reprod Dev. 2019 Nov 15. doi: 10.1262/jrd.2019-085. [Epub ahead of print] PubMed PMID: 31735743. 18: Sakamoto T, Saito Y, Kobayashi M, Yamada T, Takekuma Y, Nakai M, Ogawa K, Iseki K, Sugawara M. Effect of palonosetron and dexamethasone administration on the prevention of gastrointestinal symptoms in hepatic arterial chemoembolization with epirubicin. Support Care Cancer. 2019 Nov 16. doi: 10.1007/s00520-019-05178-1. [Epub ahead of print] PubMed PMID: 31732854. 19: Marcozzi S, Rossi V, Salvatore G, Di Rella F, De Felici M, Klinger FG. Distinct effects of epirubicin, cisplatin and cyclophosphamide on ovarian somatic cells of prepuberal ovaries. Aging (Albany NY). 2019 Nov 11;11(22):10532-10556. doi: 10.18632/aging.102476. Epub 2019 Nov 11. PubMed PMID: 31711044; PubMed Central PMCID: PMC6914390. 20: Raje S, Pandav K, Barthwal R. Dual mode of binding of anti cancer drug epirubicin to G-quadruplex [d-(TTAGGGT)](4) containing human telomeric DNA sequence induces thermal stabilization. Bioorg Med Chem. 2019 Dec 15;27(24):115131. doi: 10.1016/j.bmc.2019.115131. Epub 2019 Oct 15. PubMed PMID: 31685331.