Drug Details

General Information of the Drug (ID: DR6681)
Name
Epirubicin
Synonyms
Epirubicin; Epiadriamycin; Epidoxorubicin; 4'-Epiadriamycin; Ellence; 56420-45-2; Epirubicine; Epirubicinum; Pidorubicina; Pidorubicine; Pidorubicinum; Epirubicina; 4'-epidoxorubicin; 4-Epidoxorubicin; Epirubicin hydrochloride; Pidorubicin; Epirubicin free base; UNII-3Z8479ZZ5X; Ridorubicin; NSC 256942; CHEBI:47898; Epi-DX; Epirubicine [French]; Epirubicinum [Latin]; 3Z8479ZZ5X; Epirubicina [Spanish]; IMI 28; Epirubicine [INN-French]; Epirubicinum [INN-Latin]; Epirubicina [INN-Spanish]; Pidorubicine [INN-French]; Pidorubicinum [INN-Latin]; 56420-45-2 (FREE BASE); Pidorubicina [INN-Spanish]; Epirubicin [INN:BAN]; NSC-256942; WP 697; (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; (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; Epirubicin (INN); Farmorubicin (TN); CCRIS 2261; HSDB 6962; NSC256942; BRN 1445813; DM6; Acid, 8; CHEMBL417; SCHEMBL8582; (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; DTXSID0022987; EPIRUBICIN(Hydrochloride form); BDBM43839; Doxorubicin-13CD3 (discontinued); ZINC3938704; DB00445; VA10821; NCGC00263918-04; NCGC00263918-08; (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; 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; 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)-; HY-13624; SBI-0206890.P001; A12409; C11230; D07901; 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; AB00698552-11; AB00698552-13; AB00698552-14; AB00698552_15; AB00698552_16; A831042; Q425122; BRD-K04548931-003-16-5; (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; 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; 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)-
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Molecular Type
Small molecule
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption
The absorption of drug is 100%
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 20 mL/min/kg
Elimination
9.5% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 3 minutes (alpha), 2.5 hours (beta), and 33 hours (gamma)
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 5.7524 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.25%
Vd
The volume of distribution (Vd) of drug is 21 +/- 2 L/kg
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C27H29NO11
PubChem CID
41867
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
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
CAS Number
CAS 56420-45-2
ChEBI ID
CHEBI:47898
TTD Drug ID
D0C9XJ
DrugBank ID
DB00445
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Chrysin      Tripterygium wilfordii     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
L5178 Mouse leukemia Rattus norvegicus
                    Experimental
                    Result(s)		 Chrysin synergistically enhanced the effect of epirubicin.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Parthenolide      Tanacetum parthenium     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-468 CVCL_0419 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Parthenolide along with Epirubicin chemotherapy drug could improve cytotoxicity and apoptosis and reduces IC50.
Target and Pathway
Target(s) DNA topoisomerase II (TOP2)  Molecule Info  [4]
References
Reference 1 New drugs for the treatment of cancer, 1990-2001. Isr Med Assoc J. 2002 Dec;4(12):1124-31.
Reference 2 In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. In Vivo. Mar-Apr 2005;19(2):367-74.
Reference 3 Anticancer and apoptotic activities of parthenolide in combination with epirubicin in mda-mb-468 breast cancer cells. Mol Biol Rep. 2020 Aug;47(8):5807-5815.
Reference 4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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