epidoxorubicin

エピドキソルビシン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/24 12:13:32」(JST)

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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 category	D (Au, U.S.)
Legal status	℞-only (U.S.), POM (UK)
Routes of administration	Intravenous
Pharmacokinetic data
Bioavailability	NA
Protein binding	77%
Metabolism	Hepatic glucuronidation and oxidation
Excretion	Biliary and renal
Identifiers
CAS Registry Number	56420-45-2 Y
ATC code	L01DB03
PubChem	CID: 41867
DrugBank	DB00445 Y
ChemSpider	38201 Y
UNII	3Z8479ZZ5X Y
KEGG	D07901 Y
ChEBI	CHEBI:47898 Y
ChEMBL	CHEMBL417 Y
Chemical data
Formula	C27H29NO11
Molecular 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 Y Key:AOJJSUZBOXZQNB-VTZDEGQISA-N Y
Y (what is this?)  (verify)

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. 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.

References

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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• 1. 進行性（ステージIII～IV）の古典型ホジキンリンパ腫の初期治療 initial treatment of advanced stage iii iv classical hodgkin lymphoma

English Journal

• Carboplatin, methotrexate, vinblastine, and epirubicin (M-VECa) as salvage treatment in patients with advanced bladder cancer: a phase II study.

• Petrioli R1, Roviello G, Fiaschi AI, Laera L, Miano ST, Bianco V, Francini E.
• Anti-cancer drugs.Anticancer Drugs.2015 Sep;26(8):878-83. doi: 10.1097/CAD.0000000000000254.
• The primary objective of this study was to determine the activity and safety of carboplatin, methotrexate, vinblastine, and epirubicin (the M-VECa regimen) in patients with advanced bladder cancer after failure of at least one chemotherapy line. Treatment consisted of carboplatin 250 mg/m on day 1
• PMID 26053279

• Chemotherapy for Uterine Carcinosarcoma with Carboplatin, Ifosfamide and Mesna.

• Dandamudi RK1, Aslam S2, Walji N2, El-Modir A2, Fernando I2.
• Anticancer research.Anticancer Res.2015 Sep;35(9):4841-7.
• BACKGROUND/AIM: Uterine carcinosarcomas (UCSs) are highly aggressive, rare, biphasic tumors composed of epithelial and mesenchymal elements. Surgery remains the mainstay of treatment in early-stage disease. Adjuvant pelvic radiotherapy improves locoregional control without proven overall survival (O
• PMID 26254376

• Time to initiation of adjuvant chemotherapy in patients with rapidly proliferating early breast cancer.

• Farolfi A1, Scarpi E2, Rocca A3, Mangia A4, Biglia N5, Gianni L6, Tienghi A7, Valerio MR8, Gasparini G9, Amaducci L10, Faedi M3, Baldini E11, Rubagotti A12, Maltoni R3, Paradiso A13, Amadori D3.
• European journal of cancer (Oxford, England : 1990).Eur J Cancer.2015 Sep;51(14):1874-81. doi: 10.1016/j.ejca.2015.07.003. Epub 2015 Jul 20.
• AIM: To evaluate the optimal time interval from definitive surgery to commencing chemotherapy in early breast cancer (EBC).PATIENTS AND METHODS: The relationship between time to initiation of adjuvant chemotherapy (TTC), calculated in weeks, and disease-free (DFS) or overall survival (OS), was asses
• PMID 26206258

Japanese Journal

• Docetaxel plus epidoxorubicin as neoadjuvant treatment in patients with large operable or locally advanced carcinoma of the breast

• MATTEIS A
• Cancer 94, 895-901, 2002
• NAID 30007452929

• Epidoxorubicin and paclitaxel as primary chemotherapy for T>3 cm and T4 breast cancer patients

• BELLINO R
• Anticancer Res 20, 4825-4828, 2000
• NAID 80012096557

• Production of the antitumor drug epirubicin (4'-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius

• MADDURI K.
• Nat. Biotechnol. 16, 69-74, 1998
• NAID 80010094672

Related Links

• Epidoxorubicin - Antineoplastic Agents, ATC:L01DB03

Epidoxorubicin Brand names, Epidoxorubicin Analogs 4'-Epiadriamycin 4'-Epidoxorubicin Ellence Epi-Dx Epiadriamycin Epidoxorubicin Epirubicina [Inn-Spanish] Epirubicina [Spanish] Epirubicine [French] Epirubicine [Inn-French] ...

• Epirubicin | C27H29NO11 - PubChem - The PubChem Project

Epirubicin | C27H29NO11 | CID 41867 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ... NIH NLM U ...

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