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
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
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
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
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