Epirubicin hydrochloride
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 hydrochloride
- Molecular weight
- 579.99
- 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.Cl
- ellence
- Ellence
- epirubicin hydrochloride
- Epirubicin hydrochloride
- pharmorubicin
- Pharmorubicin
- (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 HYDROCHLORIDE
- 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 hydrochloride
- 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 hydrochloride 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-, HYDROCHLORIDE, (8S-CIS)-
- epirubicin hcl
- Epirubicin hcl
- EPIRUBICIN HCL [VANDF]
- epirubicin hcl vandf
- epirubicin hydrochloride
- Epirubicin hydrochloride
- EPIRUBICIN HYDROCHLORIDE [EP MONOGRAPH]
- EPIRUBICIN HYDROCHLORIDE [JAN]
- EPIRUBICIN HYDROCHLORIDE [MART.]
- EPIRUBICIN HYDROCHLORIDE [MI]
- EPIRUBICIN HYDROCHLORIDE [ORANGE BOOK]
- EPIRUBICIN HYDROCHLORIDE [USAN]
- EPIRUBICIN HYDROCHLORIDE [USP MONOGRAPH]
- EPIRUBICIN HYDROCHLORIDE [USP-RS]
- Epirubicin hydrochloride [WHO-DD]
- epirubicin hydrochloride ep monograph
- epirubicin hydrochloride jan
- epirubicin hydrochloride mart
- epirubicin hydrochloride mi
- epirubicin hydrochloride orange book
- epirubicin hydrochloride usan
And 13 more, listed on the interactive page.
- CAS registry numbers
- 56390-09-1
- ChEMBL ID
- CHEMBL1200981
- InChIKey
- MWWSFMDVAYGXBV-FGBSZODSSA-N
- RxNorm IDs (RxCUI)
- 203213
- FDA ingredient codes (UNII)
- 22966TX7J5
- 65348
- 53630345
- Applicant
- PFIZER INC
- Approval date
- 15 Sept 1999
- Application number
- NDA050778
- Patents
- 0
- Designations
- 1
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- Yes
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- Drug name stem
- -rubicin
Administration routes
- Parenteral
Mechanisms of action
- Mechanism
- DNA inhibitor
- Action type
- Inhibitor
- Target
- DNA
- Condition
- Carcinoma, Hepatocellular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000182
- Subject identifier
- D006528
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Adenocarcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000228
- Subject identifier
- D000230
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Carcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000313
- Subject identifier
- D002277
- Condition
- Melanoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000389
- Subject identifier
- D008545
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000503
- Subject identifier
- D013274
- Condition
- Leukemia
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000565
- Subject identifier
- D007938
- Condition
- Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Mesothelioma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000588
- Subject identifier
- D008654
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Sarcoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000691
- Subject identifier
- D012509
- Condition
- Small Cell Lung Carcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000702
- Subject identifier
- D055752
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Esophageal Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0002916
- Subject identifier
- D004938
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003869
- Subject identifier
- D001943
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003897
- Subject identifier
- D013274
- Condition
- Triple Negative Breast Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005537
- Subject identifier
- D064726
- Condition
- Breast Neoplasms, Male
- Highest recorded phase
- 1
- Condition identifier
- EFO:0006861
- Subject identifier
- D018567
- Condition
- Inflammatory Breast Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:1000984
- Subject identifier
- D058922
- Condition
- Sarcoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001968
- Subject identifier
- D012509
- 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
- Peritoneal Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0002087
- Subject identifier
- D010534
And 8 more, listed on the interactive page.
- Condition identifier
- EFO_0000182
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000220
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000305
- Condition identifier
- EFO_0000389
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 3
- Condition identifier
- EFO_0002916
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003897
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0001056
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0001187
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0002447
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0003219
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004950
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004952
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004964
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004967
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0004970
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0004989
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0004992
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005036
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005040
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005070
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005089
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005102
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005105
- Highest recorded phase
- 2
And 13 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- 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
- 29
- Reporting signal score
- 47.0548
- Event
- agranulocytosis
- Reports
- 119
- Reporting signal score
- 252.641
- Event
- alopecia
- Reports
- 75
- Reporting signal score
- 42.6352
- Event
- blood creatine increased
- Reports
- 20
- Reporting signal score
- 39.781
- Event
- bone marrow failure
- Reports
- 182
- Reporting signal score
- 441.048
- Event
- breast cancer metastatic
- Reports
- 30
- Reporting signal score
- 65.5068
- Event
- cardiac dysfunction
- Reports
- 16
- Reporting signal score
- 39.4622
- Event
- cardiac failure
- Reports
- 65
- Reporting signal score
- 54.5275
- Event
- cardiomyopathy
- Reports
- 34
- Reporting signal score
- 44.3767
- Event
- colony stimulating factor therapy
- Reports
- 10
- Reporting signal score
- 47.1217
- Event
- ejection fraction decreased
- Reports
- 35
- Reporting signal score
- 44.8411
- Event
- extravasation
- Reports
- 22
- Reporting signal score
- 37.5985
- Event
- fall
- Reports
- 5
- Reporting signal score
- 41.2537
- Event
- febrile neutropenia
- Reports
- 180
- Reporting signal score
- 276.459
- Event
- hepatic artery stenosis
- Reports
- 11
- Reporting signal score
- 50.6807
- Event
- hepatic function abnormal
- Reports
- 70
- Reporting signal score
- 83.9179
- Event
- hypertransaminasaemia
- Reports
- 26
- Reporting signal score
- 53.3376
- Event
- interstitial lung disease
- Reports
- 62
- Reporting signal score
- 54.8293
- Event
- leukopenia
- Reports
- 129
- Reporting signal score
- 174.453
- Event
- metastases to bone
- Reports
- 34
- Reporting signal score
- 53.1797
- Event
- metastases to liver
- Reports
- 31
- Reporting signal score
- 46.3814
- Event
- mucosal inflammation
- Reports
- 41
- Reporting signal score
- 37.8267
- Event
- myelosuppression
- Reports
- 111
- Reporting signal score
- 300.466
- Event
- neoplasm progression
- Reports
- 87
- Reporting signal score
- 159.024
- Event
- neutropenia
- Reports
- 192
- Reporting signal score
- 176.132
And 7 more, listed on the interactive page.
- NCT00002529
- NCT00002542
- NCT00002784
- NCT00002870
- NCT00002953
- NCT00003012
- NCT00003577
- NCT00003893
- NCT00004237
- NCT00005581
- NCT00008034
- NCT00010140
- NCT00014222
- NCT00017095
- NCT00033683
- NCT00039546
- NCT00047099
- NCT00053911
- NCT00055679
- NCT00066443
- NCT00070278
- NCT00072319
- NCT00196872
- NCT00253500
- NCT00288002
And 88 more, listed on the interactive page.
- Dose
- 100-120 mg/m2
- Route
- Intravenous
- How often
- Every 3 to 4 weeks or every 21 to 28 days
- Administer into tubing of a freely flowing intravenous infusion (0.9% sodium chloride or 5% glucose solution)
- Infuse over 15-20 minutes for initial therapy, may be decreased but not less than 3 minutes if lower doses needed
- Hydrogen bond acceptors
- 12
- Hydrogen bond donors
- 6
- Polar surface area
- 206.07
- Calculated partition coefficient (ALogP)
- 0
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 40
- Molecular formula
- C27H30ClNO11
- Monoisotopic mass
- 579.1507385
- Natural product
- Yes
- 0009-5091
- 0009-5093
- Recorded assays
- 738
- Active assays
- 185
- Confirmatory
- Other
- Screening
- Antibiotics, Antineoplastic
- Topoisomerase II Inhibitors
Related records
Trials (375)
- "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 Boserolimab (MK-5890) With Pembrolizumab and Chemotherapy in People With Early Triple-Negative Breast Cancer (MK-5890-003)
- 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 3 Study to Evaluate the Safety and Efficacy of APL-1202 as a Single-agent Oral Treatment Versus Intravesical Instillation of Epirubicin Hydrochloride in naïve Intermediate-risk NMIBC Patients
- 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 Study of Dose Density Regimen With Fluorouracil, Epirubicin and Cyclophosphamide at Days 1, 4 Every 14 Days With Filgrastim Support Followed by Weekly Paclitaxel in Women With Primary 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
Approved for (4)
- Breast cancer
- Breast carcinoma
- Breast neoplasm
- Neoplasm
In development for (29)
- Acute lymphoblastic leukemia Phase 3
- Adenocarcinoma Phase 3
- Carcinoma Phase 3
- Carcinoma of esophagus Phase 3
- Cutaneous melanoma Phase 2
- Endometrial cancer Phase 3
- Esophageal cancer Phase 3
- Exocrine pancreatic carcinoma Phase 2
- Fallopian tube cancer Phase 3
- Gastric adenocarcinoma Phase 3
- Gastric cancer Phase 3
- Gastric neoplasm Phase 3
- Hepatocellular carcinoma Phase 3
- Inflammatory breast carcinoma Phase 1
- Leukemia Phase 2
- Liver cancer Phase 2
- Lung cancer Phase 3
- Lymphoma Phase 3
- Male breast carcinoma Phase 1
- Mesothelioma Phase 2