Epirubicin hydrochloride Chemical Properties

Melting point:

185°C dec.

alpha 

D20 +274° (c = 0.01 in methanol)

RTECS 

QI9295750

Flash point:

443.8℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in DMSO to 100mM, or in ethanol to 10mM

form 

powder

color 

red to deep red

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.

InChIKey

MWWSFMDVAYGXBV-UAOJCOQHSA-N

SMILES

C12=C(O)C3=C(C(=O)C4=C(C3=O)C=CC=C4OC)C(O)=C1[C@@]([H])(O[C@H]1O[C@@H](C)[C@H](O)[C@@H](N)C1)C[C@](O)(C(=O)CO)C2.Cl

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-63-62-46-40

Safety Statements 

36/37/38-45-46

WGK Germany 

3

HS Code 

29419090

Epirubicin hydrochloride Usage And Synthesis

Description

Epirubicin hydrochloride is an antitumor antibiotic which is epimeric with doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas, as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is reported to be less sardiotoxic than doxorubicin.

Description

Epirubicin is a stereoisomer of the antitumor anthracycline doxorubicin that undergoes β-glucuronidation, which partially detoxifies the dose-limiting side effects that are present with doxorubicin. Compared to doxorubicin, epirubicin is equally cytotoxic to HeLa cells (ID₅₀s = 9 μM). When used either alone or in combination therapies, epirubicin has been shown to demonstrate high rates of complete or partial remission in various cancers including advanced ovary, lymphomas, breast, pancreas, gastric, hepatocellular carcinoma, head and neck tumors, and colorectal.

Chemical Properties

Orange-Red Crystalline Solid

Originator

Erbamont (Italy)

Uses

Used as an antineoplastic

Uses

Cell-permeable anthracycline anti-tumor antibiotic

brand name

Ellence(Pfizer);FARMORUBICIN.

Biological Functions

This stereoisomer of doxorubicin has the 4′-hydroxy group of the daunosamine sugar oriented in the β-position . Epirubicin will be slowly reduced to the active C13 alcohol (epirubicinol), giving it a 30- to 38-hour half life, which is similar to that of doxorubicin. Unlike doxorubicinol, however, which was equally active with doxorubicin, epirubicinol has only one-tenth the activity of its parent drug and is not believed to contribute significantly to the therapeutic action of this agent.

Biological Activity

Antibiotic antitumor agent. Inhibits the synthesis and function of DNA (IC 50 = 62.7 μ M in rat glioblastoma cell lines) and inhibits the relaxing property of topoisomerase II.

Clinical Use

Epirubicin is indicated for use in breast cancer, and the starting dose is 100 to 120 mg/m2 (compared to a starting dose of 60–75 mg/m2 for doxorubicin).

Side effects

The side effects and precautions are as outlined previously for doxorubicin, although there is a lower risk of serious myocardial toxicity or myelotoxicity.

Drug interactions

Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine - increased risk of agranulocytosis.
Ciclosporin: increased risk of neurotoxicity
Cytotoxics: possible increased risk of cardiotoxicity with trastuzumab - avoid for up to 28 weeks after stopping trastuzumab.
Ulcer-healing drugs: concentration increased by cimetidine.
Vaccines: avoid with live vaccines

Metabolism

Cleavage of the epimerized sugar will occur before excretion, generating an aglycone that is indistinguishable from that generated by doxorubicin. Although excretion is primarily biliary, dosage reduction in severe renal impairment, as well as in hepatic dysfunction, is warranted.

storage

+4°C

References

1) Cersosimo?et al. (1986),?Epirubicin: a review of the pharmacology, clinical activity, and adverse effects of an adriamycin analogue; J. Clin. Oncol.,?4?425 2) Spadari?et al. (1986),?DNA polymerases and DNA topoisomerases as targets for the development of anticancer drugs; Anticancer Res.,?6?935 3) Minotti?et al. (2004),?Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity; Pharmacol. Rev.,?56?185 4) Mercuro?et al. (2007),?Early epirubicin-induced myocardial dysfunction revealed by serial tissue Doppler echocardiography: correlation with inflammatory and oxidative stress markers; Oncologist,?12?1124

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