References of (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
Title: Epirubicin
CAS Registry Number: 56420-45-2
CAS Name: (8
S,10
S)-10-[(3-Amino-2,3,6-trideoxy-a-L-
arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
Synonyms: 3-glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-tridioxy-a-L-arabino-hexopyranoside; 4￠-epidoxorubicin; 4￠-epiadriamycin; pidorubicin; 4￠-epi-DX
Manufacturers' Codes: IMI-28
Molecular Formula: C27H29NO11
Molecular Weight: 543.52
Percent Composition: C 59.66%, H 5.38%, N 2.58%, O 32.38%
Literature References: Analog of the anthracycline antibiotic doxorubicin,
q.v., differing only in the position of the C-4 hydroxy group of the sugar moiety. Prepn: F. Arcamone
et al., DE 2510866;
eidem, US 4058519 (1975, 1977 both to Soc. Farmaceut. Italia);
eidem, J. Med. Chem. 18, 703 (1975); S. Penco,
Process Biochem. 15(5), 12 (1980). Purification: E. Oppici
et al., BE 898506;
eidem, GB 2133005 (both 1984 to Farmitalia Carlo Erba). Comparison with doxorubicin of
in vitro activity: A. Di Marco
et al., Cancer Res. 36, 1962 (1976). Tissue distribution: C. Italia
et al., Br. J. Cancer 47, 545 (1983); F. Arcamone
et al., Cancer Chemother. Pharmacol. 12, 157 (1984). HPLC determn in biological fluids: P. E. Deesen, B. Leyland-Jones,
Drug Metab. Dispos. 12, 9 (1984); G. Cassinelli
et al., ibid. 506. Clinical trials in solid tumors: K. Kolaric
et al., J. Cancer Res. Clin. Oncol. 106, 148 (1983). Review of activity in experimental tumors: A. Goldin
et al., Invest. New Drugs 3, 3-21 (1985). Review of pharmacology and clinical efficacy: F. Ganzina,
Cancer Treat. Rev. 10, 1-22 (1983); R. J. Cersosimo, W. K. Hong,
J. Clin. Oncol. 4, 425-439 (1986); P. Hurteloup, F. Ganzina,
Drugs Exp. Clin. Res. 13, 233-246 (1986). Review of epirubicin and other anthracycline antineoplastics: R. B. Weiss
et al., Cancer Chemother. Pharmacol. 18, 185-97 (1986).
Derivative Type: Hydrochloride
CAS Registry Number: 56390-09-1
Trademarks: Ellence (Pharmacia & Upjohn); Farmorubicina (Pharmacia)
Molecular Formula: C27H29NO11.HCl
Molecular Weight: 579.98
Percent Composition: C 55.91%, H 5.21%, N 2.42%, O 30.34%, Cl 6.11%
Properties: Red-orange crystals, mp 185° (dec). [a]D20 +274° (c = 0.01 in methanol). Solution should be protected from sunlight.
Melting point: mp 185° (dec)
Optical Rotation: [a]D20 +274° (c = 0.01 in methanol)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor.
![CAS No:56420-45-2 (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,<br />11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,<br />12-dione](/structure/cas-564/56420-45-2.png)
