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  1. General Info
  2. Effects Info
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Drug Details
01. General Information
Name Epirubicin
PubChem CID 41867
Molecular Weight 543.5g/mol
Synonyms

Epirubicin, Epidoxorubicin, Epiadriamycin, 4'-Epiadriamycin, 56420-45-2, 4'-epidoxorubicin, Epirubicine, Ridorubicin, Ellence, Epirubicina, Epirubicinum, Pidorubicina, Pidorubicine, Pidorubicinum, Farmorubicin, Epi-DX, 4-Epidoxorubicin, Epirubicinum [Latin], Epirubicine [INN-French], Epirubicinum [INN-Latin], Epirubicina [INN-Spanish], Pidorubicine [INN-French], Pidorubicinum [INN-Latin], Pidorubicina [INN-Spanish], 4'-epi-Doxorubicin, Pidorubicin, Epirubicin free base, WP 697, CCRIS 2261, HSDB 6962, Epirubicin (INN), NSC-256942, UNII-3Z8479ZZ5X, BRN 1445813, CHEBI:47898, 3Z8479ZZ5X, 4' Epi Adriamycin, NSC 256942, (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, DTXSID0022987, Epirubicine [French], Epirubicina [Spanish], Epirubicinum (Latin), IMI 28, 56420-45-2 (FREE BASE), EPIRUBICIN [INN], Epirubicine (INN-French), Epirubicinum (INN-Latin), Epirubicin [INN:BAN], Epirubicina (INN-Spanish), Pidorubicine (INN-French), Pidorubicinum (INN-Latin), Pidorubicina (INN-Spanish), 4'-Epi-DXR, (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, 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)-, 4' Epiadriamycin, 4' Epidoxorubicin, (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, 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)-, Farmorubicin (TN), 4' Epi Doxorubicin, NSC256942, 4' Epi DXR, Epi-doxorubicin, DM6, Epi DX, Pidorubicinum (Latin), Acid, 8, EPIRUBICIN [MI], 4'-epi DX, EPIRUBICIN [HSDB], EPIRUBICIN [VANDF], CHEMBL417, SCHEMBL8582, EPIRUBICIN [WHO-DD], (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, 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)-, DTXCID202987, BDBM43839, L01DB03, DM2, DB00445, NCGC00263918-04, NCGC00263918-08, (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, HY-13624, SBI-0206890.P001, NS00069619, D07901, AB00698552-11, AB00698552-13, AB00698552-14, AB00698552_15, AB00698552_16, EN300-7410311, A831042, Q425122, BRD-K04548931-003-16-5, (1S,3S)-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-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSIDE, (1S,3S)-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-TRIDEOXY-alpha-L-ARABINO-HEXOPYRANOSIDE, (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-cis)-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-5,12-naphthacenedione, 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-trideoxy-alpha-L-arabino-hexopyranoside, 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,(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)-
Drug Type Small molecule
Formula C₂₇H₂₉NO₁₁
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 56420-45-2
ChEMBL ID CHEMBL417
ChEBI ID CHEBI:47898
TTD ID D0C9XJ
Drug Bank ID DB00445
KEGG ID C11230
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
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2D MOL 3D MOL
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Enhancing Drug Efficacy
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Combination Pair ID: 190
Ref_4
Pair Name Ursolic acid, Epirubicin
Partner Name Ursolic acid
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Autophagy
Gene Regulation Down-regulation Expression AKT1 hsa207
Up-regulation Expression ATG5 hsa9474
Up-regulation Expression ATG7 hsa10533
Up-regulation Expression BECN1 hsa8678
Up-regulation Expression MAP1LC3A hsa84557
Up-regulation Expression MAP1LC3B hsa81631
Down-regulation Expression PIK3CA hsa5290
In Vitro Model MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
Result These findings indicate that UA can dramatically enhance the sensitivity of MCF-7 and MDA-MB-231 cells to EPI by modulating the autophagy pathway. Our study may provide a new therapeutic strategy for combination therapy.
Combination Pair ID: 14
Ref_5
Pair Name Cepharanthine, Epirubicin
Partner Name Cepharanthine
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Mitochondrial fission and apoptosis
Gene Regulation Up-regulation Cleavage CASP3 hsa836
Up-regulation Expression CFL1 hsa1072
Up-regulation Expression CYCS hsa54205
Down-regulation Phosphorylation DNM1L hsa10059
Down-regulation Phosphorylation LIMK1 hsa3984
Up-regulation Expression LINC01554 KEGG ID N.A.
Up-regulation Expression MAP1LC3B hsa81631
Up-regulation Expression MFF hsa56947
Down-regulation Expression MFN1 hsa55669
Down-regulation Expression MFN2 hsa9927
Down-regulation Expression OPA1 hsa4976
Up-regulation Cleavage PARP1 hsa142
Up-regulation Expression PINK1 hsa65018
Up-regulation Expression PRKN hsa5071
Up-regulation Expression SQSTM1 hsa8878
In Vitro Model MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
BT-549 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_1092
In Vivo Model MDA-MB-231 cells were suspended in a 1:1 ratio in DMEM medium with a Matrigel basement membrane matrix . Cells (4×10⁷) were inoculated in the right legs of mice.
Result Cepharanthine sensitizes human triple negative breast cancer cells to chemotherapeutic agent epirubicin via inducing cofilin oxidation-mediated mitochondrial fission and apoptosis
Reversing Drug Resistance
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Combination Pair ID: 229
Ref_6
Pair Name Tanshinone I, Epirubicin
Partner Name Tanshinone I
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Gene Regulation Down-regulation Expression AKT1 hsa207
Up-regulation Cleavage CASP3 hsa836
Up-regulation Cleavage CASP9 hsa842
Down-regulation Expression HIF1A hsa3091
Down-regulation Expression PIK3CA hsa5290
In Vitro Model Hep-G2 Hepatoblastoma Homo sapiens (Human) CVCL_0027
Huh-7 Adult hepatocellular carcinoma Homo sapiens (Human) CVCL_0336
In Vivo Model 2×10⁶ HepG2 vector cells (100 μL) were injected subcutaneously into the left and right flanks of nude mice in the vector group. And 2×10*6 HepG2 HIF-1α cells (100 μL) were injected subcutaneously into the left and right flanks of nude mice in the HIF-1α group.
Result Our results suggested that Tan I could effectively improve the anti-tumor effect of EADM, and synergize EADM to reverse HIF-1α mediated resistance via targeting PI3K/AKT/HIF-1α signaling pathway.
Decreasing Drug Toxicity
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Combination Pair ID: 173
Ref_1
Pair Name Parthenolide, Epirubicin
Partner Name Parthenolide
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Up-regulation Expression CASP3 hsa836
In Vitro Model MDA-MB-468 Breast adenocarcinoma Homo sapiens (Human) CVCL_0419
Result According to lack of cytotoxicity of Parthenolide on normal cells that lead to reduction of drug side effects, it could be suggested as an adjuvant therapy with Epirubicin after complementary research on animal model and clinical trial.
Combination Pair ID: 443
Ref_2
Pair Name Paeonol, Epirubicin
Partner Name Paeonol
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Gene Regulation Up-regulation Expression BAX hsa581
Up-regulation Cleavage CASP3 hsa836
Down-regulation Expression MAPK1 hsa5594
Down-regulation Expression MAPK14 hsa1432
Down-regulation Expression MAPK8 hsa5599
Down-regulation Expression NFKB1 hsa4790
Up-regulation Cleavage PARP1 hsa142
In Vitro Model MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
4T1 Malignant neoplasms of the mouse mammary gland Mus musculus (Mouse) CVCL_0125
Result These findings suggest that combination of Paeonol and Epirubicin is potentially applicable for breast cancer treatment.
Combination Pair ID: 989
Ref_3
Pair Name Baicalein, Epirubicin
Partner Name Baicalein
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Induction-->Apoptosis and autophagy
Gene Regulation Up-regulation Expression ATG7 hsa10533
Up-regulation Expression BAX hsa581
Up-regulation Expression BECN1 hsa8678
Down-regulation Expression TGFB1 hsa7040
In Vitro Model Hep-G2 Hepatoblastoma Homo sapiens (Human) CVCL_0027
WI-38 Healthy Homo sapiens (Human) CVCL_0579
Result BTME (200μg/mL) significantly enhanced epirubicin's cytotoxicity against Hep-G2 cells and ameliorated its safety profile. BTME could exert anti-hepatocarcinoma effect by enhancing apoptosis and autophagy
04. Reference
No. Title Href
1 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. doi: 10.1007/s11033-020-05649-3. Click
2 Enhanced antitumor activity and attenuated cardiotoxicity of Epirubicin combined with Paeonol against breast cancer. Tumour Biol. 2016 Sep;37(9):12301-12313. doi: 10.1007/s13277-016-5088-9. Click
3 Chemotherapeutic effect of baicalein/epirubicin combination against liver cell carcinoma in-vitro: Inducing apoptosis and autophagy. Toxicol In Vitro. 2024 Mar;95:105744. doi: 10.1016/j.tiv.2023.105744. Click
4 Ursolic Acid Enhances the Sensitivity of MCF-7 and MDA-MB-231 Cells to Epirubicin by Modulating the Autophagy Pathway. Molecules. 2022 May 25;27(11):3399. doi: 10.3390/molecules27113399. Click
5 Cepharanthine sensitizes human triple negative breast cancer cells to chemotherapeutic agent epirubicin via inducing cofilin oxidation-mediated mitochondrial fission and apoptosis. Acta Pharmacol Sin. 2022 Jan;43(1):177-193. doi: 10.1038/s41401-021-00715-3. Click
6 Combined Treatment of Tanshinone I and Epirubicin Revealed Enhanced Inhibition of Hepatocellular Carcinoma by Targeting PI3K/AKT/HIF-1α. Drug Des Devel Ther. 2022 Sep 19;16:3197-3213. doi: 10.2147/DDDT.S360691. Click
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