(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

Base Information

• Chemical Name: (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
• CAS No.: 56390-09-1
• Molecular Formula: C27H29NO11.HCl
• Molecular Weight: 579.99
• Hs Code.: 29419090
• Mol file: 56390-09-1.mol

Synonyms:

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:

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:

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-]
• 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.
• Uses: Cell-permeable anthracycline anti-tumor antibiotic
• 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.
• 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).
• 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