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a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/28 21:20:19」(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[edit]

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[edit]

^ 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".
^ According to the proprietary database iddb.com

External links[edit]

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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1. 限局進行性で切除不能の転移性食道癌および胃癌に対する全身療法 systemic therapy for locally advanced unresectable and metastatic esophageal and gastric cancer
2. 筋層非浸潤性膀胱癌の治療 treatment of non muscle invasive bladder cancer
3. 進行性膵外分泌癌に対する化学療法 chemotherapy for advanced exocrine pancreatic cancer
4. アントラサイクリン系化学療法剤の心毒性 cardiotoxicity of anthracycline like chemotherapy agents
5. 食道癌の治療プロトコル treatment protocols for esophagogastric cancer

English Journal

Bevacizumab-induced small bowel perforation in a patient with breast cancer without intraabdominal metastases.

Lecarpentier E, Ouaffi L, Mir O, Berveiller P, Maurel M, Pujade-Lauraine E, Bouillot JL, Veyrie N.SourceDepartment of Digestive and general surgery, Teaching Hospital Cochin, AP-HP, Paris, France.
Investigational new drugs.Invest New Drugs.2011 Dec;29(6):1500-3. Epub 2010 Jul 31.
A 53-years-old woman presented with sudden abdominal pain. One year before, she was diagnosed an inflammatory ductal carcinoma of the left breast (T3N0M0) and received 6 cycles of epirubicin and cyclophosphamide followed by 9 cycles of paclitaxel. A radical left mastectomy with lymphadenectomy was p
PMID 20676743

Cytostatic activity of the duplex drug linking 2'-deoxy-5-fluorouridine (5FdU) with 3'-C-ethynylcytidine (ECyd) against gastric adenocarcinoma cell lines.

Weinreich J, Schott S, Konigsrainer I, Zieker D, Konigsrainer A, Schott H.SourceDepartment of General, Visceral and Transplant Surgery, University of Tubingen, Tubingen, Germany, juergen.weinreich@med.uni-tuebingen.de.
Investigational new drugs.Invest New Drugs.2011 Dec;29(6):1294-302. Epub 2010 Jul 2.
The cytostatic potential of the new duplex drug 2'-deoxy-5-fluorouridylyl-(5'[Symbol: see text]5')-3'-C-ethynylcytidine (5FdU(5'-5')ECyd) was evaluated in comparison to those of 5-fluorouracil (5FU), 2'-deoxy-5-fluorourindine (5FdU), 3'-C-ethynylycytidine (ECyd), cisplatin, an equimolar mixture of 5
PMID 20596746

Japanese Journal

CDDP肝動注化学療法が著効した肝細胞癌の1例

須藤訓,岩久章,板垣宗徳,石黒晴哉,瀬嵐康之,小池和彦,穂苅厚史,石川智久,高木一郎,伊坪真理子,田尻久雄
肝臓 51(1), 21-27, 2010-01-25
症例は61歳，男性．C型肝硬変にて当科通院中に，2006年6月肝S4領域に肝細胞癌を認め，エピルビシンによる肝動脈化学塞栓療法（以下TACE）を施行した．その後再発なく経過したが，2007年4月肝S4領域にHCCを認めたため再度エピルビシンによるTACE施行した．しかし病変の一部は胃十二指腸動脈，胆嚢動脈より栄養されており，3回目の治療はシスプラチン（動注用アイエーコール）を用いた肝動注化学療法（ …
NAID 10026101099

外来化学療法における末梢神経障害の特徴に基づく看護支援の検討 : - 副作用症状の自己記録ノートの分析から -

高橋裕美,神田清子,武居明美,外丸冨美子,瀬山留加,二渡玉江,堀越政孝
北関東医学 60(2), 143-149, 2010
【目　的】　外来化学療法を受ける患者の末梢神経障害の特徴を把握し, 看護支援を検討する.　【対象と方法】　A病院の外来化学療法センターに通院している患者84名を対象とし, 自己記録ノートにおいて, 治療当日から3クール治療前日までの最長43日間の末梢神経障害の項目を調査した.　【結　果】　FOLFOX (フルオロウラシル, オキサリプラチン) : 81％と高い割合で出現しており, ピークは治療後4 …
NAID 130000259031

「エピルビシン」

Epirubicin
Systematic (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
Clinical data
Trade names	Ellence
AHFS/Drugs.com	monograph
MedlinePlus	a603003
Pregnancy cat.	D (Au, U.S.)
Legal status	℞-only (U.S.), POM (UK)
Routes	Intravenous
Pharmacokinetic data
Bioavailability	NA
Protein binding	77%
Metabolism	Hepatic glucuronidation and oxidation
Excretion	Biliary and renal
Identifiers
CAS number	56420-45-2
ATC code	L01DB03
PubChem	CID 41867
DrugBank	DB00445
ChemSpider	38201
UNII	3Z8479ZZ5X
KEGG	D07901
ChEBI	CHEBI:47898
ChEMBL	CHEMBL417
Chemical data
Formula	C27H29NO11
Mol. mass	543.519 g/mol
	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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