(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 328
• Molecular Formular: C27H29NO11
• Molecular Mass: 543.51926
• Monoisotopic Mass: 543.17406075
• SMILES: O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2)C(=O)CO)[C@@H]1O[C@H]([C@H](O)[C@@H](N)C1)C
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• 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
• InChIKey: AOJJSUZBOXZQNB-VTZDEGQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: epirubicin
• Brand Name: 4'-Epiadriamycin; 4'-Epidoxorubicin; Ellence; Epi-Dx; Epiadriamycin; Epidoxorubicin; Epirubicina [INN-Spanish]; Epirubicina [Spanish]; Epirubicine [French]; Epirubicine [INN-French]; Epirubicinum [INN-Latin]; Epirubicinum [Latin]; IMI 28; Pharmorubicin Pfs; Pidorubicina [INN-Spanish]; Pidorubicine [INN-French]; Pidorubicinum [INN-Latin]; Ridorubicin
• Synonyms: Epirubicin

Database IDs

• CAS Number: 56420-45-2
• PubChem SID: 46507282; 160963791
• PubChem CID: 41867

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.53088
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.4428744
• LogD (pH = 7.4): -0.27556196
• Log P: 0.91642165
• Molar Refractivity: 134.5937 cm^3
• Polarizability: 52.692078 Å^3
• Polar Surface Area: 206.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.41
• LOG S: -2.67
• Solubility (Water): 1.18e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.093 mg/ml
• Hydrophobicity(logP): -0.5

DETAILS

DrugBank - DB00445

• Drug Groups: approved
• Description: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. [PubChem]
• Indication: For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer.
• Pharmacology: Epirubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Epirubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Epirubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
• Toxicity: bone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding
• Affected Organisms: Humans and other mammals
• Biotransformation: Extensively and rapidly metabolized in the liver. Epirubicin is also metabolized by other organs and cells, including red blood cells. The four main metabolic routes are: (1) reduction of the C-13 keto-group with the formation of the 13(S)-dihydro derivative, epirubicinol; (2) conjugation of both the unchanged drug and epirubicinol with glucuronic acid; (3) loss of the amino sugar moiety through a hydrolytic process with the formation of the doxorubicin and doxorubicinol aglycones; and (4) loss of the amino sugar moiety through a redox process with the formation of the 7-deoxy-doxorubicin aglycone and 7-deoxy-doxorubicinol aglycone. Epirubicinol exhibits in vitro cytoxic activity (~10% that of epirubicin), but it is unlikely to reach sufficient concentrations in vivo to produce cytotoxic effects.
• Absorption: 100%
• Half Life: Half-lives for the alpha, beta, and gamma phases of about 3 minutes, 2.5 hours and 33 hours, respectively
• Protein Binding: 77%
• Elimination: Epirubicin and its major metabolites are eliminated through biliary excretion and, to a lesser extent, by urinary excretion.
• Distribution: * 21 ± 2 L/kg [60 mg/m2 Dose]; * 27 ± 11 L/kg [75 mg/m2 Dose]; * 23 ± 7 L/kg [120 mg/m2 Dose]; * 21 ± 7 L/kg [150 mg/m2 Dose]
• Clearance: * 65 +/- 8 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 60 mg/m2]; * 83 +/- 14 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 75 mg/m2]; * 65 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 120 mg/m2]; * 69 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 150 mg/m2]
• References: Pharmacia. Ellence? (epirubicin hydrochloride injection) full prescribing information. New York, NY; 2007 Feb.
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Pharmacia. Ellence? (epirubicin hydrochloride injection) full prescribing information. New York, NY; 2007 Feb.