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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/04/21 12:58:59」(JST)

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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. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere.

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.

Development history

The first trial of epirubicin in humans was published in 1980.^[1] 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.^[2] It appears to have been licensed for use in Europe from around this time however.^[3] 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.

References

^ Bonfante, V; Bonadonna, G; Villani, F; Martini, A (1980). "Preliminary clinical experience with 4-epidoxorubicin in advanced human neoplasia". Recent results in cancer research. 74: 192–9. PMID 6934564. PM6934564.
^ "On Target". Archived from the original on 2008-05-10.
^ According to the proprietary database iddb.com

External links

http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Epirubicin.htm
http://www.pfizerpro.com/page_not_found?rid=/wyeth_html/home/minisites/oncology/ellence/pi/description.html

UpToDate Contents

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English Journal

The contribution of Raman spectroscopy to the analytical quality control of cytotoxic drugs in a hospital environment: eliminating the exposure risks for staff members and their work environment.

Bourget P1, Amin A2, Vidal F3, Merlette C3, Troude P4, Baillet-Guffroy A5.
International journal of pharmaceutics.Int J Pharm.2014 Aug 15;470(1-2):70-6. doi: 10.1016/j.ijpharm.2014.04.064. Epub 2014 May 2.
The purpose of the study was to perform a comparative analysis of the technical performance, respective costs and environmental effect of two invasive analytical methods (HPLC and UV/visible-FTIR) as compared to a new non-invasive analytical technique (Raman spectroscopy). Three pharmacotherapeutic
PMID 24792972

Surgical Outcome after Neoadjuvant Chemotherapy and Bevacizumab: Results from the GeparQuinto Study (GBG 44).

Gerber B1, von Minckwitz G, Eidtmann H, Rezai M, Fasching P, Tesch H, Eggemann H, Schrader I, Kittel K, Hanusch C, Solbach C, Jackisch C, Kunz G, Blohmer JU, Huober J, Hauschild M, Nekljudova V, Loibl S, Untch M.
Annals of surgical oncology.Ann Surg Oncol.2014 Aug;21(8):2517-24. doi: 10.1245/s10434-014-3606-9. Epub 2014 Apr 18.
PURPOSE: Bevacizumab, a humanized monoclonal antibody against vascular endothelial growth factor, has shown increased pathological complete response rates when added to neoadjuvant chemotherapy. In various cancer types, bevacizumab treatment was accompanied by an increased risk of bleedings and othe
PMID 24740826

Liposomes, modified with PTDHIV-1 peptide, containing epirubicin and celecoxib, to target vasculogenic mimicry channels in invasive breast cancer.

Ju RJ1, Li XT1, Shi JF1, Li XY1, Sun MG1, Zeng F1, Zhou J1, Liu L1, Zhang CX1, Zhao WY1, Lu WL2.
Biomaterials.Biomaterials.2014 Aug;35(26):7610-21. doi: 10.1016/j.biomaterials.2014.05.040. Epub 2014 Jun 7.
Refractoriness of invasive breast cancer is closely related with the vasculogenic mimicry (VM) channels, which exhibit highly drug resistance to conventional chemotherapies. In the present study, the nanostructured targeting epirubicin plus celecoxib liposomes were developed by modifying a human imm
PMID 24912818

Japanese Journal

Reversible Cardiomyopathy After Epirubicin Administration

Koitabashi Norimichi,Ohyama Yoshiaki,Tateno Rieko,Arai Masashi,Rokutanda Nana,Horiguchi Jun,Kurabayashi Masahiko
International Heart Journal advpub(0), 2015
… Epirubicin, which is widely used for breast cancer chemotherapy, is an anthracycline that has less cardiac toxicity than doxorubicin. … The present report describes the case of a 70-year-old woman with breast cancer who developed severe congestive heart failure and severe cardiac dysfunction at 6 weeks from epirubicin final administration. … To the best of our knowledge, this is the first report to describe epirubicin-induced subacute reversible cardiotoxicity. …
NAID 130005084046

注射剤による血管障害の発現回避に向けた薬理学的検討並びに薬学的介入

山田孝明
薬学雑誌. 乙号 135(3), 465-472, 2015
… Pharmaceutical intervention and pharmacological mechanisms used to reduce vascular injury induced by vinorelbine and epirubicin were reviewed. … On the other hand, the phlebitis scores were significantly higher in patients treated with epirubicin ready-to-use solution compared with lyophilized powder. … The change of formulation of epirubicin to lyophilized powder decreased the risk of venous irritation. …
NAID 130004756520

Epirubicinおよびtrastuzumab投与により心不全を呈した乳癌術後の1例

木内俊介,久武真二,冠木敬之 [他]
循環器内科 76(4), 434-438, 2014-10
NAID 40020244509

Related Pictures

★リンクテーブル★

リンク元	「エピルビシン」「アントラサイクリン」「EPI」
拡張検索	「epirubicin hydrochloride」

「エピルビシン」

Epirubicin
Clinical data
Trade names	Ellence
AHFS/Drugs.com	Monograph
MedlinePlus	a603003
Pregnancy; category	AU: D; US: D (Evidence of risk); ;
Routes of; administration	Intravenous
ATC code	L01DB03 (WHO);
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	NA
Protein binding	77%
Metabolism	Hepatic glucuronidation and oxidation
Excretion	Biliary and renal
Identifiers
	IUPAC name (8R,10S)-10-((2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione;
CAS Number	56420-45-2 ;
PubChem CID	41867;
DrugBank	DB00445 ;
ChemSpider	38201 ;
UNII	3Z8479ZZ5X;
KEGG	D07901 ;
ChEBI	CHEBI:47898 ;
ChEMBL	CHEMBL417 ;
Chemical and physical data
Formula	C27H29NO11
Molar mass	543.519 g/mol
3D model (Jmol)	Interactive image;
	SMILES O=C2c1c(O)c5c(c(O)c1C(=O)c3cccc(OC)c23)C[C@@](O)(C(=O)CO)C[C@@H]5O[C@@H]4O[C@H]([C@H](O)[C@@H](N)C4)C ;
	InChI 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 ; Key:AOJJSUZBOXZQNB-VTZDEGQISA-N ;
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