Chemical Property of (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydron;chloride
Chemical Property:
- Appearance/Colour:Orange-red crystalline solid
- Vapor Pressure:9.64E-28mmHg at 25°C
- Melting Point:185 °C dec
- Refractive Index:1.709
- Boiling Point:810.3 °C at 760 mmHg
- Flash Point:443.8 °C
- PSA：206.07000
- Density:1.61 g/cm3
- LogP:1.50360
- Storage Temp.:Desiccate at +4°C
- Solubility.:Soluble in DMSO to 100mM, or in ethanol to 10mM
- Hydrogen Bond Donor Count:7
- Hydrogen Bond Acceptor Count:13
- Rotatable Bond Count:5
- Exact Mass:579.1507385
- Heavy Atom Count:40
- Complexity:977
- Purity/Quality:
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98%MIN *data from raw suppliers
Epirubicin, Hydrochloride *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn
- Hazard Codes:Xn
- Statements:
22-63-62-46-40
- Safety Statements:
36/37/38-45-46
- MSDS Files:
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SDS file from LookChem
Useful:
- Canonical SMILES:[H+].CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.[Cl-]
- Isomeric SMILES:[H+].C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.[Cl-]
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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. 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.
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Uses
Cell-permeable anthracycline anti-tumor antibiotic
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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.
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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).
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Drug interactions
Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine - increased risk
of agranulocytosis.Ciclosporin: increased risk of neurotoxicityCytotoxics: 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
