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Drug

D0049 | Epirubicin

Molecular Formula C27H29NO11
Molecular Weight 543.5
Structure
State solid
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]
Volume of 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]
Route of elimination Epirubicin and its major metabolites are eliminated through biliary excretion and, to a lesser extent, by urinary excretion.
Protein binding 0.77
Half life Half-lives for the alpha, beta, and gamma phases of about 3 minutes, 2.5 hours and 33 hours, respectively
Absorption 1
Trade names Ellence, Pharmorubicin, Epirubicin Ebewe
Description anthracycline drug used for chemotherapy; intercalating DNA strands

L

L01DB03 Epirubicin


[L01DB] Anthracyclines and related substances


[L01D] CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents

Pictogram Signal Statements Precautionary Statement Codes
Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]


 P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 intraperitoneal 16mg/kg (16mg/kg) Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1075, 1972.
man LDLo unreported 243ug/kg (0.243mg/kg) Postgraduate Medical Journal. Vol. 68, Pg. 69, 1992.
mouse LD50 intraperitoneal 10700ug/kg (10.7mg/kg) Huaxi Yike Daxue Xuebao. Journal of West China University of Medical Sciences. Vol. 20, Pg. 303, 1989.
human LDLo intravenous 400ug/kg (0.4mg/kg) Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972.
hamster LD10 parenteral 3500ug/kg (3.5mg/kg) Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
mouse LD50 unreported 21900ug/kg (21.9mg/kg) Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
mouse LD50 intravenous 10mg/kg (10mg/kg) Journal of Antibiotics. Vol. 45, Pg. 1373, 1992.
human TDLo intravenous 380mg/kg/31W (380mg/kg) Cancer Vol. 34, Pg. 518, 1974.
rabbit LDLo intrapleural 400ug/kg (0.4mg/kg) Pharmacology and Toxicology Vol. 62, Pg. 84, 1988.
rat LD50 unreported 7mg/kg (7mg/kg) Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 34, Pg. 216, 1989.
rat LD50 intravenous 10510ug/kg (10.51mg/kg) Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.
mammal (species unspecified) LD50 intraperitoneal 8500ug/kg (8.5mg/kg) Antibiotiki. Vol. 29, Pg. 748, 1984.
rabbit LD50 intravenous 5mg/kg (5mg/kg) Yiyao Gongye. Pharmaceutical Industry. Vol. 17, Pg. 72, 1986.
human TDLo intravenous 15mg/kg/D (15mg/kg) Cancer Vol. 34, Pg. 518, 1974.
mouse LD50 oral 570mg/kg (570mg/kg) Antibiotiki. Vol. 28, Pg. 298, 1983.
dog LD50 intravenous 2400ug/kg (2.4mg/kg) Drug and Chemical Toxicology. Vol. 6, Pg. 21, 1983.
mouse LDLo intratracheal 2400ug/kg (2.4mg/kg) Toxicology Letters. Vol. 30, Pg. 63, 1986.


  • (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside (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-alpha-L-arabino-hexopyranoside (7S,9R)-7-[(2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
    (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione (7S,9S)-7-[(2R,4S,5R,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-4-methoxy-6,9,11-tris(oxidanyl)-9-(2-oxidanylethanoyl)-8,10-dihydro-7H-tetracene-5,12-dione (7S,9S)-7-[[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
    (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 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione 15206-EP2269994A1
    15206-EP2270008A1 15206-EP2270018A1 15206-EP2272827A1
    15206-EP2275420A1 15206-EP2280012A2 15206-EP2281815A1
    15206-EP2289892A1 15206-EP2292615A1 15206-EP2292617A1
    15206-EP2295055A2 15206-EP2295416A2 15206-EP2295426A1
    15206-EP2295427A1 15206-EP2298748A2 15206-EP2298764A1
    15206-EP2298765A1 15206-EP2298768A1 15206-EP2298778A1
    15206-EP2298780A1 15206-EP2301928A1 15206-EP2301933A1
    15206-EP2305640A2 15206-EP2305642A2 15206-EP2305671A1
    15206-EP2305689A1 15206-EP2308855A1 15206-EP2308861A1
    15206-EP2311453A1 15206-EP2311808A1 15206-EP2311825A1
    15206-EP2311827A1 15206-EP2311829A1 15206-EP2311840A1
    15206-EP2311842A2 15206-EP2316832A1 15206-EP2316833A1
    3Z8479ZZ5X 4'-Epi-DXR 4'-Epiadriamycin
    4'-Epidoxorubicin|||4'-Epiadriamycin|||(8S,10S)-10-(((2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione 4'-epi-Doxorubicin 4'-epidoxorubicin
    4-Epidoxorubicin 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)- 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
    5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)- 5,12-Naphthacenedione,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-, (8S,10S)- 56420-45-2
    A12409 A831042 AB00698552-11
    AB00698552-13 AB00698552-14 AB00698552_15
    AB00698552_16 AK326115 AOJJSUZBOXZQNB-VTZDEGQISA-N
    Acid, 8 BDBM43839 BRD-K04548931-003-16-5
    BRN 1445813 C11230 CCRIS 2261
    CHEBI:47898 CHEMBL417 CS-2824
    CTK8F9465 D07901 DB00445
    DTXSID0022987 Doxorubicin-13CD3 (discontinued) EPIRUBICIN(Hydrochloride form)
    Ellence Epi-DX Epiadriamycin
    Epidoxorubicin Epirubicin Epirubicin (INN)
    Epirubicin [INN:BAN] Epirubicina Epirubicina [INN-Spanish]
    Epirubicina [Spanish] Epirubicine Epirubicine [French]
    Epirubicine [INN-French] Epirubicinum Epirubicinum [INN-Latin]
    Epirubicinum [Latin] FT-0630692 Farmorubicin (TN)
    HSDB 6962 HY-13624 IMI 28
    LS-187190 LS-93992 NCGC00263918-04
    NSC 256942 NSC-256942 NSC256942
    Pidorubicin Pidorubicina Pidorubicina [INN-Spanish]
    Pidorubicine Pidorubicine [INN-French] Pidorubicinum
    Pidorubicinum [INN-Latin] Q425122 Ridorubicin
    SBI-0206890.P001 SCHEMBL8582 UNII-3Z8479ZZ5X
    VA10821 WP 697 ZINC3938704

    DrugBank Name Epirubicin
    DrugBank DB00445
    CAS Number 23214-92-8, 56390-09-1, 56420-45-2
    PubChem Compound 41867
    KEGG Compound ID C11230
    KEGG Drug D07901
    PubChem.Substance 46507282
    ChEBI 47898
    PharmGKB PA449476
    ChemSpider 38201
    BindingDB 43839.0
    TTD DAP000193
    Wikipedia Epirubicin
    DPD 20259

    1. Dykens et al. (2007)