Epirubicin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1999
- First approval year
- 1999
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Epirubicin
- Molecular weight
- 543.53
- Structure (SMILES)
- COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1
- (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
- 4 epi adriamycin
- 4'-epi-adriamycin
- 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-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-
- epiadriamycin
- Epiadriamycin
- epidoxorubicin
- Epidoxorubicin
- epidoxorubicin and cisplatin and lipiodol
- epirubicin
- Epirubicin
- EPIRUBICIN [HSDB]
- epirubicin [INN]
- EPIRUBICIN [MI]
- EPIRUBICIN [VANDF]
- Epirubicin [WHO-DD]
- epirubicin hsdb
- epirubicin inn
- epirubicin mi
- epirubicin vandf
- epirubicin who dd
- epirubicina
- Epirubicina
And 7 more, listed on the interactive page.
- ATC classification codes
- L01DB03
Sources for recorded values
- CAS registry numbers
- 56420-45-2
- ChEMBL ID
- CHEMBL417
- InChIKey
- AOJJSUZBOXZQNB-VTZDEGQISA-N
- PubChem compound IDs
- 41867
- FDA ingredient codes (UNII)
- 3Z8479ZZ5X
- 3995
- 203213
- Applicant
- PFIZER INC
- Approval date
- 15 Sept 1999
- Application number
- NDA050778
- Patents
- 0
- Designations
- 2
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- United States (FDA)
- Approved
- Drug name stem
- -rubicin
Administration routes
- Parenteral
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Carcinoma, Hepatocellular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000182
- Subject identifier
- D006528
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Lymphoma, Large B-Cell, Diffuse
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000403
- Subject identifier
- D016403
- Condition
- Neoplasms, Germ Cell and Embryonal
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000514
- Subject identifier
- D009373
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Small Cell Lung Carcinoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000702
- Subject identifier
- D055752
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Carcinoma, Non-Small-Cell Lung
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003060
- Subject identifier
- D002289
- Condition
- Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003869
- Subject identifier
- D001943
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003897
- Subject identifier
- D013274
- Condition
- Testicular Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0004281
- Subject identifier
- D013736
- Condition
- Triple Negative Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0005537
- Subject identifier
- D064726
- Condition
- Lymphoma, Non-Hodgkin
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005952
- Subject identifier
- D008228
- Condition
- Thymoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:1000581
- Subject identifier
- D013945
- Condition
- Inflammatory Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:1000984
- Subject identifier
- D058922
- Condition
- Sarcoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001968
- Subject identifier
- D012509
- Condition
- Sepsis
- Highest recorded phase
- 2
- Condition identifier
- HP:0100806
- Subject identifier
- D018805
- Condition
- Thrombosis
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0000831
- Subject identifier
- D013927
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0001056
- Subject identifier
- D013274
- Condition
- Urinary Bladder Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0001187
- Subject identifier
- D001749
- Condition
- Adenocarcinoma
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0003219
- Subject identifier
- D000230
- Condition
- Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0007254
- Subject identifier
- D001943
- Condition
- Esophageal Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0007576
- Subject identifier
- D004938
- Condition
- Ovarian Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0008170
- Subject identifier
- D010051
And 3 more, listed on the interactive page.
- Condition identifier
- EFO_0000182
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000294
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000478
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000514
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000564
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000702
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003869
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003967
- Highest recorded phase
- 1
- Condition identifier
- EFO_0005537
- Highest recorded phase
- 3
- Condition identifier
- EFO_0005952
- Highest recorded phase
- 2
- Condition identifier
- EFO_0006834
- Highest recorded phase
- 2
- Condition identifier
- EFO_1000984
- Highest recorded phase
- 3
- Condition identifier
- HP_0100806
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0000430
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0000831
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0001056
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0001187
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0001187
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002087
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002142
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002158
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002447
- Condition identifier
- MONDO_0002926
- Highest recorded phase
- 1
And 59 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Country
- United States
- Event
- acute myeloid leukaemia
- Reports
- 423
- Reporting signal score
- 791.045
- Event
- alopecia
- Reports
- 300
- Reporting signal score
- 312.886
- Event
- anaemia
- Reports
- 1,612
- Reporting signal score
- 758.288
- Event
- bone marrow failure
- Reports
- 527
- Reporting signal score
- 604.909
- Event
- breast cancer metastatic
- Reports
- 64
- Reporting signal score
- 137.113
- Event
- breast cancer recurrent
- Reports
- 56
- Reporting signal score
- 151.454
- Event
- cardiac dysfunction
- Reports
- 59
- Reporting signal score
- 175.202
- Event
- cardiac failure
- Reports
- 150
- Reporting signal score
- 130.51
- Event
- cardiomyopathy
- Reports
- 464
- Reporting signal score
- 688.415
- Event
- cardiotoxicity
- Reports
- 615
- Reporting signal score
- 1,440.88
- Event
- diffuse large b-cell lymphoma
- Reports
- 274
- Reporting signal score
- 544.906
- Event
- diffuse large b-cell lymphoma recurrent
- Reports
- 307
- Reporting signal score
- 973.313
- Event
- disease progression
- Reports
- 1,266
- Reporting signal score
- 1,160.77
- Event
- disease recurrence
- Reports
- 571
- Reporting signal score
- 768.979
- Event
- ejection fraction decreased
- Reports
- 476
- Reporting signal score
- 693.499
- Event
- febrile neutropenia
- Reports
- 4,149
- Reporting signal score
- 9,305.6
- Event
- haematotoxicity
- Reports
- 556
- Reporting signal score
- 1,152.16
- Event
- leukopenia
- Reports
- 852
- Reporting signal score
- 761.459
- Event
- malignant neoplasm progression
- Reports
- 760
- Reporting signal score
- 612.554
- Event
- metastases to bone
- Reports
- 151
- Reporting signal score
- 334.118
- Event
- metastases to liver
- Reports
- 126
- Reporting signal score
- 259.577
- Event
- metastases to lung
- Reports
- 66
- Reporting signal score
- 120.751
- Event
- metastases to lymph nodes
- Reports
- 70
- Reporting signal score
- 159.051
- Event
- metastasis
- Reports
- 83
- Reporting signal score
- 209.48
- Event
- mucosal inflammation
- Reports
- 963
- Reporting signal score
- 1,506.56
And 9 more, listed on the interactive page.
- NCT00038402
- NCT00054587
- NCT00087178
- NCT00097383
- NCT00129922
- NCT00129935
- NCT00162812
- NCT00176488
- NCT00193024
- NCT00193050
- NCT00193206
- NCT00309556
- NCT00309569
- NCT00322374
- NCT00336791
- NCT00378313
- NCT00424606
- NCT00429871
- NCT00431080
- NCT00431795
- NCT00432172
- NCT00464646
- NCT00499603
- NCT00527449
- NCT00540800
And 165 more, listed on the interactive page.
- Dose
- 100-120 mg/m2
- Route
- Intravenous
- How often
- Every 3-4 weeks
- Administration as an intravenous bolus
- Infused over 15-20 minutes for initial doses, less than 3 minutes if dose reduced
- Hydrogen bond acceptors
- 12
- Hydrogen bond donors
- 6
- Polar surface area
- 206.07
- Calculated partition coefficient (ALogP)
- 0
- Calculated partition coefficient (XLogP)
- 1.3
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 39
- Molecular formula
- C27H29NO11
- Monoisotopic mass
- 543.17406074
- Natural product
- Yes
- Recorded assays
- 1,469
- Active assays
- 312
- Confirmatory
- Other
- Screening
- Summary
- Antibiotics, Antineoplastic
- Topoisomerase II Inhibitors
Related records
Trials (276)
- "Phase II Study of PET Guided Neoadjuvant Chemotherapy (NAC) and Oncotype Guided Hormonal Therapy of Breast Cancer"
- 4 x Epirubicin, Cyclophosphamide, Followed by 4 x Docetaxel Versus 6 x CMF / 6 x CEF
- 5-FU, Leucovorin, Oxaliplatin and Docetaxel (FLOT) Versus Epirubicin, Cisplatin and 5-FU (ECF) in Patients With Locally Advanced, Resectable Gastric Cancer
- 6xFU/Epirubicin/Cyclophosphamide (FEC) Compared to 3xFEC-3xDocetaxel in High-risk Node-negative Breast Cancer Patients
- A Clinical Study of Sacituzumab Tirumotecan (Sac-TMT, MK-2870) in People With Breast Cancer (MK-2870-032)
- A Clinical Trial to Evaluate the Efficacy and Safety of Anotinib Hydrochloride Capsule Combined With Epirubicin Hydrochloride Versus Placebo Combined With Epirubicin Hydrochloride in First-line Treatment of Advanced Soft Tissue Sarcoma
- A Feasibility Study to Evaluate Adjuvant Chemoradiotherapy for Gastric Cancer
- 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
- A Multicenter Trial Comparing Induction C/T Followed by CCRT v.s. CCRT Alone in Stage IV Nasopharyngeal Carcinoma
- A Phase I, Open-label, Study of Pazopanib in Combination With Epirubicin or Doxorubicin for Advanced Solid Tumors
- A Phase II Study Evaluating the Efficacy and Safety of Pembrolizumab in Combination With Chemotherapy as Neoadjuvant Therapy for Triple-negative Breast Cancer
- A Phase II Trial of Epirubicin, Oxaliplatin and Capecitabine (EOX) Versus Docetaxel and Oxaliplatin (ElTax) in the Treatment of Advanced Gastro-oesophageal Cancer
- 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
- A Phase III Study of KN026 in Combination With HB1801 as Adjuvant Therapy for Resectable HER2-Positive Breast Cancer
- A Phase III Trial Comparing Two Dose-dense, Dose-intensified Approaches (ETC and PM(Cb)) for Neoadjuvant Treatment of Patients With High-risk Early Breast Cancer (GeparOcto)
- A Phase III Trial to Compare the Efficacy, Safety and Pharmacokinetics of HD201 to Herceptin® in HER2+ Early Breast Cancer Patients
- A Pilot Dose Escalation Trial of a Densified Chemotherapy Association of Docetaxel and Epirubicin Driven by Mathematical Modeling in Metastatic Breast Cancer Patients: The MODEL1 Study
- A Prospective, Phase II, Exploratory Study Protocol of a Chemotherapy Sensitivity-based Culmerciclib Combination Regimen in Neoadjuvant Therapy for HR+/HER2- Breast Cancer.
- A Randomized Trial Comparing EC-wPversus EP-wP as Adjuvant Therapy for Operable Breast Cancer Patients Less Than 40 Years Old
- A Randomized Trial of Chemotherapy in Surgical Patients With Infiltrating Ductal Carcinoma of Breast
Approved for (1)
In development for (68)
- Acute lymphoblastic leukemia Phase 2
- Adenocarcinoma Phase 2
- Adenoid cystic carcinoma Phase 2
- Alveolar soft part sarcoma Phase 1
- Angiosarcoma Phase 1
- B-cell chronic lymphocytic leukemia Phase 2
- B-cell non-Hodgkin lymphoma Phase 3
- Bone sarcoma Phase 1
- Breast cancer Phase 3
- Breast carcinoma Phase 2
- Breast neoplasm Phase 3
- Cancer Phase 3
- Classic Hodgkin lymphoma Phase 2
- Clear cell sarcoma Phase 1
- Dedifferentiated chondrosarcoma Phase 1
- Diffuse large B-cell lymphoma Phase 3
- Esophageal adenocarcinoma Phase 3
- Esophageal cancer Phase 2
- Esophageal squamous cell carcinoma Phase 2
- Estrogen-receptor negative breast cancer Phase 2
Other linked conditions (3)
- Endometrial carcinoma
- Urinary bladder carcinoma
- Urinary bladder neoplasm