WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100290
CAS#: 56390-09-1 (HCl)
Description: Epirubicin hydrochloride is the hydrochloride salt of the 4'-epi-isomer of the anthracycline antineoplastic antibiotic doxorubicin. Epirubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent also produces toxic free-radical intermediates and interacts with cell membrane lipids causing lipid peroxidation.
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
Related CAS #: 56420-45-2 (free base) 56390-09-1 (HCl)
Synonym: IMI28; IMI 28; IMI-28; 4-epi DX; EPI; epi DX; 4-epiadriamycin; 4-epidoxorubicin; 4-epidoxorubicin HCl; epiADR; epidoxorubicin; pidorubicin; 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
ELLENCE Injection (epirubicin hydrochloride injection) is an anthracycline cytotoxic agent, intended for intravenous administration. ELLENCE is supplied as a sterile, clear, red solution and is available in polypropylene vials containing 50 and 200 mg of epirubicin hydrochloride as a preservative-free, ready-to-use solution. Each milliliter of solution contains 2 mg of epirubicin hydrochloride. Inactive ingredients include sodium chloride, USP, and water for injection, USP. The pH of the solution has been adjusted to 3.0 with hydrochloric acid, NF. Epirubicin hydrochloride is the 4-epimer of doxorubicin and is a semi-synthetic derivative of daunorubicin. The chemical name is (8S- cis)-10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride. The active ingredient is a red-orange hygroscopic powder, with the empirical formula C27 H29 NO11 HCl and a molecular weight of 579.95.
Epirubicin is an anthracycline cytotoxic agent. Although it is known that anthracyclines can interfere with a number of biochemical and biological functions within eukaryotic cells, the precise mechanisms of epirubicin's cytotoxic and/or antiproliferative properties have not been completely elucidated. Epirubicin forms a complex with DNA by intercalation of its planar rings between nucleotide base pairs, with consequent inhibition of nucleic acid (DNA and RNA) and protein synthesis. Such intercalation triggers DNA cleavage by topoisomerase II, resulting in cytocidal activity. Epirubicin also inhibits DNA helicase activity, preventing the enzymatic separation of double-stranded DNA and interfering with replication and transcription. Epirubicin is also involved in oxidation/reduction reactions by generating cytotoxic free radicals. The antiproliferative and cytotoxic activity of epirubicin is thought to result from these or other possible mechanisms. Epirubicin is cytotoxic in vitro to a variety of established murine and human cell lines and primary cultures of human tumors. It is also active in vivo against a variety of murine tumors and human xenografts in athymic mice, including breast tumors.
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. It appears to have been licensed for use in Europe from around this time however. 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. Patent protection for epirubicin expired in August 2007. from http://en.wikipedia.org/wiki/Epirubicin.
1: Khasraw M, Bell R, Dang C. Epirubicin: is it like doxorubicin in breast cancer? A clinical review. Breast. 2012 Apr;21(2):142-9. doi: 10.1016/j.breast.2011.12.012. Epub 2012 Jan 17. Review. PubMed PMID: 22260846.
2: Shang PF, Kwong J, Wang ZP, Tian J, Jiang L, Yang K, Yue ZJ, Tian JQ. Intravesical Bacillus Calmette-GuÃ©rin versus epirubicin for Ta and T1 bladder cancer. Cochrane Database Syst Rev. 2011 May 11;(5):CD006885. doi: 10.1002/14651858.CD006885.pub2. Review. PubMed PMID: 21563157.
3: Mir O, Berveiller P, Rouzier R, Goffinet F, Goldwasser F, Treluyer JM. Chemotherapy for breast cancer during pregnancy: is epirubicin safe? Ann Oncol. 2008 Oct;19(10):1814-5. doi: 10.1093/annonc/mdn553. Epub 2008 Sep 2. Review. PubMed PMID: 18765465.
4: Petrioli R, Fiaschi AI, Francini E, Pascucci A, Francini G. The role of doxorubicin and epirubicin in the treatment of patients with metastatic hormone-refractory prostate cancer. Cancer Treat Rev. 2008 Dec;34(8):710-8. doi: 10.1016/j.ctrv.2008.05.004. Epub 2008 Jul 11. Review. PubMed PMID: 18620815.
5: Reni M, Cereda S, Galli L. PEFG (cisplatin, epirubicin, 5-fluorouracil, gemcitabine) for patients with advanced pancreatic cancer: the ghost regimen. Cancer Lett. 2007 Oct 18;256(1):25-8. Epub 2007 Jun 11. Review. PubMed PMID: 17561341.
6: GlÃ¼ck S. Adjuvant chemotherapy for early breast cancer: optimal use of epirubicin. Oncologist. 2005 Nov-Dec;10(10):780-91. Review. PubMed PMID: 16314288.
7: Untch M, von Koch F, Kahlert S, Konecny G. Overview of epirubicin-based adjuvant therapy in breast cancer. Clin Breast Cancer. 2000 Sep;1 Suppl 1:S41-5. Review. PubMed PMID: 15959941.
8: Nakashima R, Enomoto T, Murata Y, Fujita M. [Activity of paclitaxel, epirubicin and carboplatin in patients with advanced or recurrent endometrial cancer]. Nihon Rinsho. 2004 Oct;62 Suppl 10:360-4. Review. Japanese. PubMed PMID: 15535268.
9: Earl H, Iddawela M. Epirubicin as adjuvant therapy in breast cancer. Expert Rev Anticancer Ther. 2004 Apr;4(2):189-95. Review. PubMed PMID: 15056049.