| Identification | Back Directory | [Name]
Epirubicin hydrochloride | [CAS]
56390-09-1 | [Synonyms]
Adrial
Ellence
Epirubin HCI
Farmorubicin-RTU
Epirubicin HCl API
EpirubicinHc,LEp5,
(8s-cis)-rochlorid
Epirubicin hydrochloride
Epidoxorubicin hydrochloride
Epirubicin, Hydrochloride Salt
4’-epi-adriamycinhydrochloride
Epirubicin hydrochloride, >=99%
Epirubicin Hydrochloride (200 mg)
EPIRUBICIN HYDROCHLORIDE EP STANDARD
Ellence, Farmorubicin, Pharmorubicin
Epirubicin HCl
Epirubicin hydrochloride
(8S-cis)-4'-Epidoxorubicin Hydrochloride
Epirubicin hydrochloride(4'-Epidoxorubicin)
8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-l)oxy)-hyd
5,12-naphthacenedione,10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosy
(8S,10S)-10-(((2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-tri
(8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedionehydrochloride
(8S-cis)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride
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,10S)-
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)-
5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-
(8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, hydrochloride (1:1)
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-(2-hydroxyacetyl)-1-methoxy-, hydrochloride (1:1), (8S,10S)- | [EINECS(EC#)]
260-145-2 | [Molecular Formula]
C27H30ClNO11 | [MDL Number]
MFCD00941448 | [MOL File]
56390-09-1.mol | [Molecular Weight]
579.98 |
| Chemical Properties | Back Directory | [Appearance]
Orange-Red Crystalline Solid | [Melting point ]
185°C dec. | [alpha ]
D20 +274° (c = 0.01 in methanol) | [RTECS ]
QI9295750 | [Fp ]
443.8℃ | [storage temp. ]
Desiccate at +4°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 |
| Hazard Information | Back Directory | [Chemical Properties]
Orange-Red Crystalline Solid | [Uses]
Used as an antineoplastic | [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. | [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. | [Originator]
Erbamont (Italy) | [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. | [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 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 | [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, protect from light | [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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