Epirubicin

Summary

Epirubicin (CHEMBL417) is an approved small-molecule EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (ATC L01DB03); indicated across 28 conditions including neoplasm and hepatocellular carcinoma; with CIViC clinical evidence for 1 variant-indication association (e.g. FOXP3 EXPRESSION in breast cancer).

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01DB03
• Indications: 28 conditions
• Clinical trials: 251
• Precision-oncology evidence (CIViC): 1 variant–indication association
• Chemistry: 543.5 Da · C27H29NO11

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL417
Name	Epirubicin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	41867
ChEBI	CHEBI:47898
ATC	L01DB03
Molecular formula	C27H29NO11
Molecular weight	543.5
InChIKey	AOJJSUZBOXZQNB-VTZDEGQISA-N

SMILES: C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O

IUPAC name: (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

ChEBI definition: An anthracycline that is the 4’-epi-isomer of doxorubicin.

Pharmacological roles (ChEBI): EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, antineoplastic agent, antimicrobial agent.

Also known as: 4’-epi-adriamycin, Epiadriamycin, Epidoxorubicin, Epirubicin, Epirubicina, Epirubicine, Farmorubicin, NSC-256942, 4’-epiadriamycin, epirubicin, EPIRUBICINE, 14C-Epirubicin

Parent form; salt/anhydrous children: CHEMBL1200981

Patent coverage: 33,671 distinct patent families (135,503 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 135,001 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: DNA topoisomerase 2-alpha, Tyrosine-protein kinase Fyn, Thromboxane A2 receptor, Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1, Acetylcholinesterase, Prostaglandin G/H synthase 1, Alpha-1A adrenergic receptor, 3’,5’-cyclic-AMP phosphodiesterase 4A, 5-hydroxytryptamine receptor 4.

Bioactivity

ChEMBL activities: 7 potent at pChembl ≥ 5 of 11 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
TOP2A	8.52	IC50	3	nM	CHEMBL_ACT_25724246
O70528	5.88	Ki	1323	nM	CHEMBL_ACT_7656500
PTGS1	5.61	AC50	2441	nM	CHEMBL_ACT_25206158
FYN	5.29	IC50	5181	nM	CHEMBL_ACT_7656477
O70528	5.1	IC50	7935	nM	CHEMBL_ACT_7656499
TBXA2R	5.09	AC50	8168	nM	CHEMBL_ACT_25211095
ADRA1A	5.05	AC50	8859	nM	CHEMBL_ACT_25208529

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

28 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
neoplasm	4	MONDO:0005070	EFO:0000616
hepatocellular carcinoma	3	MONDO:0007256	EFO:0000182
diffuse large B-cell lymphoma	3	MONDO:0018905	EFO:0000403
breast neoplasm	3	MONDO:0021100	EFO:0003869
triple-negative breast carcinoma	3	MONDO:0005494	EFO:0005537
inflammatory breast carcinoma	3	MONDO:0006804	EFO:1000984
thrombotic disease	3	MONDO:0000831	MONDO:0000831
gastric neoplasm	3	MONDO:0021085	MONDO:0001056
soft tissue sarcoma	3	MONDO:0018078	EFO:1001968
peripheral T-cell lymphoma, not otherwise specified	3	MONDO:0004964	EFO:0000211
nasopharyngeal carcinoma	3	MONDO:0015459	MONDO:0015459
germ cell tumor	2	MONDO:0005040	EFO:0000514
exocrine pancreatic carcinoma	2	MONDO:0005192	EFO:0002618
non-small cell lung carcinoma	2	MONDO:0005233	EFO:0003060
testicular cancer	2	MONDO:0005447	EFO:0004281
non-Hodgkin lymphoma	2	MONDO:0018908	EFO:0005952
small cell lung carcinoma	2	MONDO:0008433	EFO:0000702
ovarian cancer	2	MONDO:0008170	MONDO:0008170
Hodgkins lymphoma	2	MONDO:0004952	MONDO:0009348
neoplasm of mature B-cells	2	MONDO:0004949	EFO:0000096
thymoma	2	MONDO:0006456	EFO:1000581
adenocarcinoma	2	MONDO:0004970	MONDO:0003219

6 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 251.

Phase distribution

Phase	Trials
PHASE2	122
PHASE3	73
Not specified	17
PHASE4	11
PHASE2/PHASE3	11
PHASE1/PHASE2	10
PHASE1	6
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT05420454	PHASE4	RECRUITING	A Study for the Neoadjuvant Treatment of Breast Cancer
NCT05420467	PHASE4	RECRUITING	A Study for the Adjuvant Treatment of Breast Cancer
NCT00531973	PHASE4	UNKNOWN	A Study of Liposomal Doxorubicin in Women With Breast Cancer Exploiting Tissue Doppler Imaging
NCT01199432	PHASE4	COMPLETED	Comparative Efficiency of Three Regimen, CEFci, CEF and EC as Neoadjuvant Chemotherapy for Primary Breast Cancer
NCT02207361	PHASE4	UNKNOWN	Paclitaxel in Combination With Carboplatin Versus Paclitaxel Plus Epirubicin in Metastatic Breast Cancer
NCT02214602	PHASE4	COMPLETED	Value of Immediate Post-operative Intravesical Epirubicin in Intermediate&High Risk Non Muscle Invasive Bladder Cancer
NCT02549677	PHASE4	COMPLETED	Epirubicin Versus Docetaxel Plus Cyclophosphamide in Lymph Node Negative, ER-positive, Her2-negative Breast Cancer
NCT02627248	PHASE4	UNKNOWN	Neoadjuvant Chemotherapy With or Without Huaier Granule in Treating Women With Locally Advanced Breast Cancer That Can Be Removed By Surgery
NCT02631499	PHASE4	UNKNOWN	Efficacy Study of TACE to Treat Hepatocellular Carcinoma After Operation
NCT02752815	PHASE4	UNKNOWN	Reduced Chemotherapy in Low Risk DLBCL
NCT03123770	PHASE4	UNKNOWN	Efficacy and Safety of Neoadjuvant DC-T in Breast Cancer Patients
NCT01924819	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Trial of Preoperative Therapy for Gastric and Esophagogastric Junction Adenocarcinoma
NCT02535221	PHASE3	RECRUITING	Neoadjuvant Endocrine Therapy Versus Chemotherapy in Premenopausal Patients With ER+ & HER2- Breast Cancer
NCT04193059	PHASE3	ACTIVE_NOT_RECRUITING	Study Comparing EC-T Verses PCb in the Adjuvant Chemotherapy of Non-triple Negative Breast Cancer
NCT04290793	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Neoadjuvant Chemotherapy With Pyrotinib, Epirubicin and Cyclophosphamide Followed by Taxanes and Trastuzumab for HER-2+ Breast Cancer
NCT04296175	PHASE3	ACTIVE_NOT_RECRUITING	Carboplatin Intensified Chemotherapy for TRIple NEgative Breast Cancer(CITRINE)
NCT04335669	PHASE3	ACTIVE_NOT_RECRUITING	NordicTrip, a Translational Study of Preoperative Chemotherapy in TNBC
NCT04576143	PHASE2/PHASE3	RECRUITING	Efficacy and Safety of Dose-dense Chemotherapy (ddEC-ddP) for Neoadjuvant Chemotherapy of HER2-negative Breast Cancer
NCT04947059	PHASE3	RECRUITING	Effectiveness of an Immediate Postoperative Intravesical Instillation With Either Gemcitabine or Epirubicin in Patients With Urinary Bladder Cancer (Gemcitabine Epirubicin Normal SAline)
NCT05678933	PHASE3	ENROLLING_BY_INVITATION	AC-CHOP Versus CHOP in Patients With Previously Untreated PTCL-TFH
NCT05862064	PHASE3	RECRUITING	A Multi-center, Randomized, Open-label, Phase III Study Comparing PD-1 Inhibitor Combined With Antivascular Therapy and Anthracycline/Taxane-based Adjuvant Chemotherapy Versus Anthracycline/Taxane-based Adjuvant Chemotherapy Alone in Patients With Operable Triple-negative Breast Cancer
NCT05883852	PHASE3	RECRUITING	EC-THP Versus TCbHP in HER2-positive Lymph Node Positive Early Breast Cancer
NCT05901428	PHASE3	RECRUITING	TCb vs EC-T in High Risk ER+/HER2- Breast Cancer
NCT06112379	PHASE3	ACTIVE_NOT_RECRUITING	A Phase III Randomised Study to Evaluate Dato-DXd and Durvalumab for Neoadjuvant/Adjuvant Treatment of Triple-Negative or Hormone Receptor-low/HER2-negative Breast Cancer
NCT06795503	PHASE3	NOT_YET_RECRUITING	Non-Inferiority Study on MRNA-lncRNA Model in Low-Risk Triple-Negative Breast Cancer Patients
NCT06966700	PHASE3	RECRUITING	A Clinical Study of Sacituzumab Tirumotecan (Sac-TMT, MK-2870) in People With Breast Cancer (MK-2870-032)
NCT07441460	PHASE3	RECRUITING	A Phase III Study of KN026 in Combination With HB1801 as Adjuvant Therapy for Resectable HER2-Positive Breast Cancer
NCT00038402	PHASE3	COMPLETED	Evaluation of the Addition of Herceptin to Standard Chemotherapy in the Neoadjuvant Setting for Operable Breast Cancer
NCT00054587	PHASE3	COMPLETED	Combination Chemotherapy With or Without Trastuzumab in Treating Women With Breast Cancer
NCT00087178	PHASE3	COMPLETED	Comparison of Two Combination Chemotherapy Regimens in Treating Women With Breast Cancer
NCT00123318	PHASE3	COMPLETED	A Feasibility Study to Evaluate Adjuvant Chemoradiotherapy for Gastric Cancer
NCT00129922	PHASE3	COMPLETED	Fluorouracil, Epirubicin, and Cyclophosphamide Alone or Followed by Paclitaxel for Early Breast Cancer
NCT00129935	PHASE3	COMPLETED	EC Followed Docetaxel Versus ET Followed Capecitabine as Adjuvant Chemotherapy for Node Positive Operable Breast Cancer
NCT00162695	PHASE3	TERMINATED	Rhabdomyosarcoma and Malignant Soft Tissue Tumours of Childhood
NCT00196872	PHASE3	COMPLETED	A Study to Compare ETC vs. EC-TX and Ibandronate vs. Observation in Patients With Node-positive Primary Breast Cancer (GAIN)
NCT00309556	PHASE3	COMPLETED	Randomized Neoadjuvant Study of Epirubicin and Docetaxel With/Without Capecitabine in Early Breast Cancer
NCT00309569	PHASE3	COMPLETED	Randomized Study Comparing Pre- and Postoperative vs. Conventional Adjuvant Treatment in Receptor-negative Patients
NCT00336791	PHASE3	COMPLETED	Randomized Clinical Trial to Evaluate the Predictive Accuracy of a Gene Expression for Stage I-II Breast Cancer
NCT00407186	PHASE3	UNKNOWN	Randomized Phase III Trial of Adjuvant Chemotherapy or Chemoradiotherapy in Resectable Gastric Cancer (CRITICS)
NCT00424606	PHASE3	COMPLETED	Epirubicin and Docetaxel Combination (ET) or Epirubicin Followed by Docetaxel (E/T) for Node Negative (N0) High Risk Breast Cancer Patients

Clinical evidence (CIViC)

Variant × indication × effect (1 predictive associations from 1 curated evidence items):

Variant	Indication	Effect	Therapy	Level	CIViC
FOXP3 EXPRESSION	Breast Cancer	Sensitivity/Response	Epirubicin	CIViC B	EID928

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 49 clinical and 175 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).