Epirubicin
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| Category | Antineoplastic |
| Catalog number | BBF-05862 |
| CAS | 56420-45-2 |
| Molecular Weight | 543.52 |
| Molecular Formula | C27H29NO11 |
| Purity | >98% |
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Description
Epirubicin, a semisynthetic L-arabino derivative of doxorubicin, is an antineoplastic agent by inhibiting Topoisomerase. It is clinically active against a broad range of tumor types, including breast cancer, malignant lymphomas, soft tissue sarcomas, lung cancer, pleural mesothelioma, gastrointestinal cancer, head and neck cancer, ovarian cancer, prostatic carcinoma, transitional bladder carcinoma and so on.
Specification
| Related CAS | 56390-09-1 (hydrochloride) |
| Synonyms | Pharmorubicin; Ellence; Epiadriamycin; Epidoxorubicin; 4'-Epiadriamycin; Epirubicine; Pidorubicine; NSC 256942; (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; (8S-cis)-4'-Epidoxorubicin; (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside |
| Shelf Life | > 2years. |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC 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 |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O |
| InChI | InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1 |
| InChI Key | AOJJSUZBOXZQNB-VTZDEGQISA-N |
Properties
| Appearance | Red Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 810.3±65.0°C at 760 mmHg |
| Melting Point | 344.53 °C |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Methanol (Slightly, Heated), Water (Slightly) |
| LogP | -0.5 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Epirubicin has antimitotic and cytotoxic activity. It inhibits nucleic acid (DNA and RNA) and protein synthesis through a number of proposed mechanisms of action: Epirubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It also interferes with DNA replication and transcription by inhibiting DNA helicase activity. |
Reference Reading
1.Infusion site adverse events in breast cancer patients receiving highly emetic chemotherapy with prophylactic anti-emetic treatment with aprepitant and fosaprepitant: A retrospective comparison.
Tsuda T1, Kyomori C2, Mizukami T1, Taniyama T1, Izawa N1, Horie Y1, Hirakawa M1, Ogura T1, Nakajima TE1, Tsugawa K3, Boku N1. Mol Clin Oncol. 2016 Apr;4(4):603-606. Epub 2016 Feb 5.
The incidences of infusion site adverse events in chemotherapy regimens, including anthracyclines with either fosaprepitant or aprepitant as the anti-emetic, were not highlighted in the randomized trial comparing aprepitant and fosaprepitant. The present retrospective analysis was performed in breast cancer patients receiving anthracycline-containing chemotherapy, a combination of epirubicin and cyclophosphamide with or without 5-fluorouracil as the adjuvant or neoadjuvant, at the outpatient infusion center of St. Marianna University Hospital (Kawasaki, Japan). Infusion site adverse events were retrospectively compared between the 3 months prior to and three months following switching from 3 day oral administration of aprepitant to intravenous infusion of fosaprepitant. A total of 62 patients were included in the aprepitant group and 38 in the fosaprepitant group. Of these patients, 26 (42%) in the aprepitant group and 36 patients (96%) in the fosaprepitant group experienced any grade of infusion site adverse events at least once (P<0.
2.An eco-friendly stability-indicating spectrofluorimetric method for the determination of two anticancer stereoisomer drugs in their pharmaceutical preparations following micellar enhancement: Application to kinetic degradation studies.
El-Kimary EI1, El-Yazbi AF2. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Mar 23;163:145-153. doi: 10.1016/j.saa.2016.03.034. [Epub ahead of print]
A new rapid and highly sensitive stability-indicating spectrofluorimetric method was developed for the determination of two stereoisomers anticancer drugs, doxorubicin (DOX) and epirubicin (EPI) in pure form and in pharmaceutical preparations. The fluorescence spectral behavior of DOX and EPI in a sodium dodecyl sulfate (SDS) micellar system was investigated. It was found that the fluorescence intensity of DOX and EPI in an aqueous solution of phosphate buffer pH4.0 and in the presence of SDS was greatly (about two fold) enhanced and the mechanism of fluorescence enhancement effect of SDS on DOX was also investigated. The fluorescence intensity of DOX or EPI was measured at 553nm after excitation at 497nm. The plots of fluorescence intensity versus concentration were rectilinear over a range of 0.03-2μg/mL for both DOX and EPI with good correlation coefficient (r>0.999). High sensitivity to DOX and EPI was attained using the proposed method with limits of detection of 10 and 9ng/mL and limits of quantitation of 29 and 28ng/mL, for DOX and EPI, respectively.
3.Short term quality of life with epirubicin-fluorouracil-cyclophosphamid (FEC) and sequential epirubicin/cyclophosphamid-docetaxel (EC-DOC) chemotherapy in patients with primary breast cancer - Results from the prospective multi-center randomized ADEBAR trial.
Schwentner L1, Harbeck N2, Singer S3, Eichler M3, Rack B4, Forstbauer H5, Wischnik A6, Scholz C7, Huober J7, Friedl TW7, Weissenbacher T4, Härtl K8, Kiechle M9, Janni W7, Fink V7. Breast. 2016 Apr 4;27:69-77. doi: 10.1016/j.breast.2016.03.003. [Epub ahead of print]
BACKGROUND: The recommendation for adjuvant dose-dense chemotherapy in high risk primary breast cancer is heterogeneous among guidelines. Understanding the impact on QoL is thereby a crucial factor, especially if the benefit is potentially low. This study aims to assess QoL as a secondary outcome in the prospective randomized multi-center ADEBAR trial.
4.Adjuvant Dose-Dense Chemotherapy in Breast Cancer: Standard of Care in High-Risk Patients.
Möbus V1. Breast Care (Basel). 2016 Feb;11(1):8-12. doi: 10.1159/000444004. Epub 2016 Feb 19.
Meta-analyses persistently confirm the superiority of dose-dense chemotherapy in comparison with standard chemotherapy. In contrast, individual studies have shown conflicting results. These may be explained by different risk profiles of the treated patient populations. Some trials show a significant advantage in disease-free survival (DFS) and overall survival (OS) in the estrogen receptor (ER)-negative population only, whereas trials with high-risk populations like GIM-2 (Gruppo Italiano Mammella) and AGO-iddETC (Arbeitsgemeinschaft Gynäkologische Onkologie, intense dose-dense epirubicin, paclitaxel, and cyclophosphamide) show a significant superiority in DFS and OS for both, ER-negative and ER-positive patients even after 7 and 10 years, respectively, of follow-up. In contrast, the 10-year follow-up data of the E1199/Intergroup trial no longer showed any superiority of weekly paclitaxel for ER-positive/HER2-negative patients; superiority was observed in the triple-negative subgroup only.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H29NO11
Molecular Weight (Monoisotopic Mass): 543.1741 Da
Molecular Weight (Avergae Mass): 543.5193 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
