Epirubicin (CAS 56420-45-2) — formula C27H29NO11, molecular weight 543.5.
| CAS Number | 56420-45-2 |
|---|---|
| Molecular Formula | C27H29NO11 |
| Molecular Weight | 543.5 |
| Melting Point | 344.53 |
| LogP | -0.5 |
| Applications | Uses: MEDICATION (VET), MEDICATION, Antibiotics, Antineoplastic, Topoisomerase II Inhibitors, Use (kg, approx.) in Germany (2009): >10, Consumption (g per capita, approx.) in Germany (2009): 0.000122, Calculated removal (%): 8.9, For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer., Methods of Manufacturing: Sicor developed a route from doxorubicin, in which the hydroxyl groups at C-9 and C-14 are protected as dioxanones (by reaction of doxorubicin with triethyl orthoformate), the 3'-amino group is protected as its N-trifluoroacetyl derivative, the hydroxyl groups of ring B as their trimethylsilyl derivatives, and the 4'-hydroxy group of the daunosamine residue is converted to a triflate group, which by nucleophilic substitution of the triflate by formate and then deprotection leads to, epirubicin, ., The most direct route starts with the N-trifluoroacetyl derivative of daunorubicin, which is oxidized at very low temperature (-70 °C) with dimethylsulfoxide activated by trifluroacetanhydride to afford the 4'-keto derivative. Stereoselective reduction with sodium borohydride at -30 °C gives the 4'-epi-N-trifluoroacetyl daunorubicin, which after alkaline hydrolysis of the trifluoroacetyl group can be converted into, ..., Preparation: E. Arcamone et al., German patent 2510866, eidem, United States of America patent 4058519 (1975, 1977 both to Soc. Farmaceut. Italia), Formulations, Preparations: Parenteral: Injection, for IV use only, 2 mg, mL (50 and 200 mg), Ellence (Pfizer), General Manufacturing Information: Analog of the anthracycline antibiotic doxorubicin ... differing only in the position of the C-4 hydroxy group of the the sugar moiety. |
Documented applications: Uses: MEDICATION (VET), MEDICATION, Antibiotics, Antineoplastic, Topoisomerase II Inhibitors, Use (kg, approx.) in Germany (2009): >10, Consumption (g per capita, approx.) in Germany (2009): 0.000122, Calculated removal (%): 8.9, For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer., Methods of Manufacturing: Sicor developed a route from doxorubicin, in which the hydroxyl groups at C-9 and C-14 are protected as dioxanones (by reaction of doxorubicin with triethyl orthoformate), the 3'-amino group is protected as its N-trifluoroacetyl derivative, the hydroxyl groups of ring B as their trimethylsilyl derivatives, and the 4'-hydroxy group of the daunosamine residue is converted to a triflate group, which by nucleophilic substitution of the triflate by formate and then deprotection leads to, epirubicin, ., The most direct route starts with the N-trifluoroacetyl derivative of daunorubicin, which is oxidized at very low temperature (-70 °C) with dimethylsulfoxide activated by trifluroacetanhydride to afford the 4'-keto derivative. Stereoselective reduction with sodium borohydride at -30 °C gives the 4'-epi-N-trifluoroacetyl daunorubicin, which after alkaline hydrolysis of the trifluoroacetyl group can be converted into, ..., Preparation: E. Arcamone et al., German patent 2510866, eidem, United States of America patent 4058519 (1975, 1977 both to Soc. Farmaceut. Italia), Formulations, Preparations: Parenteral: Injection, for IV use only, 2 mg, mL (50 and 200 mg), Ellence (Pfizer), General Manufacturing Information: Analog of the anthracycline antibiotic doxorubicin ... differing only in the position of the C-4 hydroxy group of the the sugar moiety..
Epirubicin is a chemical compound with CAS registry number 56420-45-2 and molecular formula C27H29NO11 (molecular weight 543.5).
CAS number: 56420-45-2
Its molecular formula C27H29NO11 comprises 27 C, 29 H, 1 N, 11 O atoms.
Also known as: Epirubicin · 表阿霉素
The CAS registry number of Epirubicin is 56420-45-2.
Molecular formula C27H29NO11, molecular weight 543.5.
It is also registered under: Epirubicin, 表阿霉素.
Recorded applications: Uses: MEDICATION (VET), MEDICATION, Antibiotics, Antineoplastic, Topoisomerase II Inhibitors, Use (kg, approx.) in Germany (2009): >10, Consumption (g per capita, approx.) in Germany (2009): 0.000122, Calculated removal (%): 8.9, For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer., Methods of Manufacturing: Sicor developed a route from doxorubicin, in which the hydroxyl groups at C-9 and C-14 are protected as dioxanones (by reaction of doxorubicin with triethyl orthoformate), the 3'-amino group is protected as its N-trifluoroacetyl derivative, the hydroxyl groups of ring B as their trimethylsilyl derivatives, and the 4'-hydroxy group of the daunosamine residue is converted to a triflate group, which by nucleophilic substitution of the triflate by formate and then deprotection leads to, epirubicin, ., The most direct route starts with the N-trifluoroacetyl derivative of daunorubicin, which is oxidized at very low temperature (-70 °C) with dimethylsulfoxide activated by trifluroacetanhydride to afford the 4'-keto derivative. Stereoselective reduction with sodium borohydride at -30 °C gives the 4'-epi-N-trifluoroacetyl daunorubicin, which after alkaline hydrolysis of the trifluoroacetyl group can be converted into, ..., Preparation: E. Arcamone et al., German patent 2510866, eidem, United States of America patent 4058519 (1975, 1977 both to Soc. Farmaceut. Italia), Formulations, Preparations: Parenteral: Injection, for IV use only, 2 mg, mL (50 and 200 mg), Ellence (Pfizer), General Manufacturing Information: Analog of the anthracycline antibiotic doxorubicin ... differing only in the position of the C-4 hydroxy group of the the sugar moiety..
Independent reference data for Epirubicin (CAS 56420-45-2), compiled from public chemistry databases.
| CAS Registry Number | 56420-45-2 |
|---|---|
| PubChem CID | 41867 |
| Molecular formula | C27H29NO11 |
| 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 |
| UNII (FDA) | 3Z8479ZZ5X |
| Molecular Weight | 543.5 |
|---|---|
| XLogP3 | 1.3 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 5 |
| Exact Mass | 543.17406074 |
| Monoisotopic Mass | 543.17406074 |
| Topological Polar Surface Area | 206 |
| Heavy Atom Count | 39 |
| Melting Point | 344.53 |
|---|---|
| Melting Point | 344.53 °C |
| Solubility | 0.093 |
| Solubility | 1.18e+00 g/L |
| LogP | -0.5 |
Epirubicin; 56420-45-2; Epiadriamycin; Epidoxorubicin; 4'-Epiadriamycin; Epirubicine; 4'-epidoxorubicin; Epirubicina; Ridorubicin; Epirubicinum; Pidorubicina; Pidorubicine; Pidorubicinum; Farmorubicin; Epirubicinum [Latin]; Pidorubicin
| Reported hazard statements | H302 |
|---|
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Epirubicin · CAS 56420-45-2 · C27H29NO11. UNII 3Z8479ZZ5X. Melting Point: 344.53; Melting Point: 344.53 °C; Solubility: 0.093.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 表阿霉素