Epirubicin
- Atc Codes:L01DB03
- CAS Codes:56390-09-1#56420-45-2
- PHARMGKB ID:56390-09-1#56420-45-2
Table of contents
- Brand Names
- Drug Combinations
- Chemistry
- Pharmacologic Category
- Mechanism of Action
- Therapeutic Use
- Pregnancy and Lactation Implications
- Contraindications
- Warnings and Precautions
- Adverse Reactions
- Caution and personalized dose adjustment in patients with the following genotypes
- Other genes that may be involved
- Substrate of
- Induces
- Drug Interactions
- Nutrition/Nutraceutical Interactions
- Dosage
- Pharmacokinetics and Pharmacodynamics
- Special Considerations
Brand Names
Europe
Austria: Epimedac, Epirubicin, Farmorubicin; Belgium: Epirubicin, Farmorubicine; Bulgaria: Epirubicin, Farmorubicin; Cyprus: Epirubicin, Farmorubicin; Czech Republic: Epimedac, Epirubicin, Farmorubicin; Denmark: Epi-Cell, Epirubicin, Farmorubicin; Estonia: Epirubicin, Farmorubicin; Finland: Epirubicin, Farmorubicin; France: Epirubicine, Farmorubicine; Germany: Axirubicin-E, Bendaepi, Epi-Cell, Epi Teva, Epirena, Epirubicin, Episachs, Eracin, Farmorubicin, Riboepi; Greece: Cenebir, Ciazil, Epibicin, Epibra, Epimedac, Epirub, Epirubicin, Farmorubicin, Megarubicin, Rubiprol; Hungary: Epimedac, Epirubicin, Farmorubicin; Ireland: Epirubicin, Pharmorubicin; Italy: Epirubicina, Farmorubicina; Latvia: Epirubicin, Farmorubicin; Lithuania: Epirubicin; Luxembourg: Farmorubicin; Netherlands: Epirubicine, Farmorubicine; Poland: Bioepicyna, Epimedac, Epirubicin, Episindan, Farmorubicin; Portugal: Epi-Cell, Epirrubicina, Farmorubicina; Romania: Epirubicin, Epirubicina, Episindan, Farmarubicin C.S., Farmorubicin RD; Slovakia: Epimedac, Epirubicin, Farmorubicin; Slovenia: Epimedac, Epirubicin, Episindan, Farmorubicin; Spain: Epirubicina, Farmorubicina; Sweden: Epirubicin, Farmorubicin; UK: Epirubicin, Pharmorubicin.
North America
Canada: Epirubicin, Pharmorubicin; USA: Ellence, Epirubicin.
Latin America
Argentina: Crisabón, Cuatroepi, Epidoxo, Epifil, Epirrubicina, Farmorubicin DR, Robanul; Brazil: Farmorubicina, Nuovodox, Tecnomax-Zodiac; Mexico: Binarín, Epilem, Epirubicina, Farmorubicín, Favicin.
Asia
Japan: Epirubicin, Farmorubicin.
Drug combinations
Epirubicin and Lactose
Epirubicin and Tamoxifen
Chemistry
Epirubicin Hydrochloride: C~27~H~29~NO~11~ HCl. Mw: 579.98. (1) 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-; (2)(1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride. CAS-56390-09-1; CAS-56420-45-2 (epirubicin)(1984).
Pharmacologic Category
Antineoplastic Agents; Cytotoxic Antibiotics and Related Substances. Anthracycline Agent. (ATC-Code: L01DB03).
Mechanism of action
Epirubicin, the 4′-epimer of doxorubicin, is an anthracycline glycoside antineoplastic antibiotic. Forms a complex with DNA by intercalation between base pairs, causing inhibition of DNA synthesis and DNA-dependent RNA synthesis by the resulting template disordering and steric obstruction. Protein synthesis is also inhibited. Such intercalation triggers DNA cleavage by topoisomerase II, resulting in cytocidal activity. DNA helicase is also inhibited, resulting in interference with replication and transcription. Epirubicin also generates cytotoxic free radicals.
Therapeutic use
Adjuvant therapy in evidence of axillary node tumor involvement following resection of primary breast carcinoma.
Pregnancy and lactiation implications
Teratogenic effects and embryotoxicity noted in animal studies. There are no adequate, well-controlled studies in pregnant women. Women of childbearing potential should avoid becoming pregnant. Men undergoing treatment should use effective contraception. Breast-feeding is contraindicated.
Unlabeled use
Contraindications
Hypersensitivity to epirubicin or any component of the formulation, other anthracyclines, or anthracenediones. Previous anthracycline treatment up to maximum cumulative dose. Severe myocardial insufficiency, severe arrhythmias. Recent MI. Severe hepatic dysfunction: Baseline neutrophil count 1500 cells/mm^3^. Pregnancy.
Warnings and precautions
Hazardous agent. Treatment with anthracyclines may increase risk of secondary leukemias. May cause tumor lysis syndrome. Use with caution in mild-to-moderate hepatic impairment. Use not recommended in severe impairment. Use with caution in renal impairment (serum creatinine >5 mg/dL). Epirubicin may have radiosensitizing activity. Possible secondary AML. Possible chromosomal damage in human spermatozoa. Possible irreversible amenorrhea in premenopausal women. Local pain, severe tissue lesions, and severe local necrosis if extravasation occurs. Not for I.M. or SubQ administration. Leukopenia, granulocytopenia, neutropenia, thrombocytopenia or anemia may occur. Early (acute) cardiotoxicity (e.g. sinus tachycardia, ECG abnormalities such as nonspecific ST-T wave changes, AV block, ventricular tachycardia). Delayed cardiotoxicity (cardiomyopathy), manifested by reduced LVEF and CHF, may be life-threatening. Cardiac effects of epirubicin and other anthracyclines or anthracenediones may be additive. Thrombophlebitis and thromboembolic phenomena, including pulmonary embolism, sometimes fatal, reported. Possible nausea and vomiting, or dose-dependent mucositis (e.g. oral stomatitis, esophagitis). Possible additive cytotoxicity with combined epirubicin and radiation therapy.