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Epirubicin
  • Synonyms: Pidorubicin, 4'-epi-Adriamycin
  • ATC: L01DB03
  • Use: Lorem  Lorem 
  • Chemical name: Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
  • Formula: Lorem ipsum dolor sit amet,
  • MW:543.53 g/mol
  • CAS-RN:56420-45-2
  • InChI Key:AOJJSUZBOXZQNB-VTZDEGQISA-N
  • 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
  • LD50: 16.07 mg/kg (M, i.v.);
    14.27 mg/kg (R, i.v.);
    2 mg/kg (dog, i.v.)

Derivatives

    hydrochloride

  • Formula: C27H29NO11 • HCl
  • MW:579.99 g/mol
  • CAS-RN:56390-09-1

Substance Classes

Synthesis Path












Substances Referenced in Synthesis Path

CAS-RN Formula Chemical Name CAS Index Name
77-76-9 C5H12O2 acetone dimethyl acetal Propane, 2,2-dimethoxy-
24385-10-2 C21H18O9 adriamycinone 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
10416-58-7 C8H21NOSi2 bis(trimethylsilyl)acetamide
21794-55-8 C21H18O8 daunomycinone 5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S-cis)-
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem
Lorem Lorem Lorem Lorem

Trade Names

Country Trade Name Vendor Annotation
D Lorem Lorem
Lorem Lorem
Lorem Lorem ,1984
Lorem Lorem
F Lorem Lorem
GB Lorem Lorem
I Lorem Lorem
J Lorem Lorem Lorem
(wfm = withdrawn from market)

Formulations

  • Loremipsumdolorsitamet,consetetursadipscingelitr,seddiam

References

    • a Arcamone, F. et al.: J. Med. Chem. (JMCMAR) 18, 999 (1975).
    •  DOS 9 999 999 (Farmitalia; appl. 20.3.1975; GB-prior. 22.3.1974).
    •  US 9 999 999 (Farmitalia; 15.11.1977; appl. 19.3.1975; GB-prior. 22.3.1974).

  • alternative preparation of the hexose chloride I from daunosamine via its tris-(trifluoroacetyl) derivative:

    • US 9 999 999 (Farmitalia; 2.8.1977; appl. 19.3.1975).

  • condensation of the hexose chloride I and aglycon with soluble silver trifluoromethanesulfonate as catalyst:

    • US 9 999 999 (Farmitalia; 5.9.1978; appl. 9.4.1976; GB-prior. 30.4.1975).
    • DE 9 999 999 (Farmitalia; appl. 29.4.1976; GB-prior. 30.4.1975).

  • enantioselective syntheses of daunosanine and acosamine:

    • Ginesta, X. et al.: Org. Lett. (ORLEF7) 5, 3001-3004 (2003).
    • b US 9 999 999 (Pharmachemie B.V.; 23.2.1999; appl. 4.12.1997; EP-prior. 16.12.1996).
    • c US 9 999 999 (Sicor; 31.8.1999; IT-prior. 22.3.1995).

  • purification:

    • GB 9 999 999 (Farmitalia; appl. 16.12.1983).
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