WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100290
CAS#: 56390-09-1 (HCl)
Description: 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. Epirubicin is favoured over doxorubicin, the most popular anthracycline, in some chemotherapy regimens as it appears to cause fewer side-effects. Epirubicin has a different spatial orientation of the hydroxyl group at the 4' carbon of the sugar - it has the opposite chirality - which may account for its faster elimination and reduced toxicity. Epirubicin is primarily used against breast and ovarian cancer, gastric cancer, lung cancer and lymphomas.
MedKoo Cat#: 100290
Name: Epirubicin hydrochloride
CAS#: 56390-09-1 (HCl)
Chemical Formula: C27H30ClNO11
Molecular Weight: 579.98
Elemental Analysis: C, 55.91; H, 5.21; Cl, 6.11; N, 2.42; O, 30.34
Synonym: 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 hydrochloride
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
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.[H]Cl
Appearance: red 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: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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
The following data is based on the product molecular weight 579.98 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.
|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|
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.
It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere. The first trial of epirubicin in humans was published in 1980. Upjohn applied for approval by the U.S. Food and Drug Administration (FDA) in node-positive breast cancer in 1984, but was turned down because of lack of data. In 1999 Pharmacia (who had by then merged with Upjohn) received FDA approval for the use of epirubicin as a component of adjuvant therapy in node-positive patients.