U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO11
Molecular Weight 543.5203
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIRUBICIN

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@@]2([H])C[C@@](Cc3c2c(c4c(C(=O)c5cccc(c5C4=O)OC)c3O)O)(C(=O)CO)O)N)O

InChI

InChIKey=AOJJSUZBOXZQNB-VTZDEGQISA-N
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

HIDE SMILES / InChI

Molecular Formula C27H29NO11
Molecular Weight 543.5203
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Epirubicin is an anthracycline cytotoxic agent, is a 4'-epi-isomer of doxorubicin. The compound is marketed by Pfizer under the trade name Ellence in the US. It is indicated as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer. Although it is known that anthracyclines can interfere with a number of biochemical and biological functions within eukaryotic cells, the precise mechanisms of epirubicin’s cytotoxic and/or antiproliferative properties have not been completely elucidated. It is known, that epirubicin forms a complex with DNA by intercalation of its planar rings between nucleotide base pairs, with consequent inhibition of nucleic acid (DNA and RNA) and protein synthesis. Such intercalation triggers DNA cleavage by topoisomerase II, resulting in cytocidal activity. Epirubicin also inhibits DNA helicase activity, preventing the enzymatic separation of double-stranded DNA and interfering with replication and transcription. Epirubicin is also involved in oxidation/reduction reactions by generating cytotoxic free radicals.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ELLENCE

Approved Use

Epirubicin Hydrochloride Injection is indicated as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer

Launch Date

9.3735361E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.7 μg/mL
60 mg/m² single, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.3 μg/mL
150 mg/m² single, intravenous
dose: 150 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.6 μg × h/mL
60 mg/m² single, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.2 μg × h/mL
150 mg/m² single, intravenous
dose: 150 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
35.3 h
60 mg/m² single, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
31.1 h
150 mg/m² single, intravenous
dose: 150 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
23%
60 mg/m² single, intravenous
dose: 60 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPIRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / 3 weeks
Sources: Page: p.13,14
unhealthy, 31–62
n = 3
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 31–62
Sex: F
Population Size: 3
Sources: Page: p.13,14
DLT: Thrombocytopenia, Leukopenia...
Dose limiting toxicities:
Thrombocytopenia (grade 4, 67%)
Leukopenia (grade 4, 67%)
Myelosuppression (grade 4, 100%)
Stomatitis (grade 3, 33%)
Sources: Page: p.13,14
95 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 95 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 95 mg/m2, 1 times / day
Sources: Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.11
Disc. AE: Aplasia bone marrow, Mucositis...
AEs leading to
discontinuation/dose reduction:
Aplasia bone marrow
Mucositis (grade 4)
Gastrointestinal bleeding
Sources: Page: p.11
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Disc. AE: Hyperthermia, Multiple organ failure...
AEs leading to
discontinuation/dose reduction:
Hyperthermia
Multiple organ failure
Lactic acidosis
Lactate dehydrogenase increased
Anuria
Sources: Page: p.11
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Disc. AE: Soft tissue necrosis...
AEs leading to
discontinuation/dose reduction:
Soft tissue necrosis (severe)
Sources: Page: p.1
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
DLT: Leukopenia, Neutropenia...
Disc. AE: Toxic myocarditis, Congestive heart failure...
Dose limiting toxicities:
Leukopenia
Neutropenia
AEs leading to
discontinuation/dose reduction:
Toxic myocarditis (severe)
Congestive heart failure (grade 3-5)
Acute promyelocytic leukemia
Myelosuppression (severe)
Hyperuricemia
Thrombophlebitis
Thromboembolic event
Pulmonary embolism
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Stomatitis grade 3, 33%
DLT, Disc. AE
200 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / 3 weeks
Sources: Page: p.13,14
unhealthy, 31–62
n = 3
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 31–62
Sex: F
Population Size: 3
Sources: Page: p.13,14
Myelosuppression grade 4, 100%
DLT, Disc. AE
200 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / 3 weeks
Sources: Page: p.13,14
unhealthy, 31–62
n = 3
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 31–62
Sex: F
Population Size: 3
Sources: Page: p.13,14
Leukopenia grade 4, 67%
DLT, Disc. AE
200 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / 3 weeks
Sources: Page: p.13,14
unhealthy, 31–62
n = 3
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 31–62
Sex: F
Population Size: 3
Sources: Page: p.13,14
Thrombocytopenia grade 4, 67%
DLT, Disc. AE
200 mg/m2 1 times / 3 weeks multiple, intravenous
MTD
Dose: 200 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 200 mg/m2, 1 times / 3 weeks
Sources: Page: p.13,14
unhealthy, 31–62
n = 3
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 31–62
Sex: F
Population Size: 3
Sources: Page: p.13,14
Aplasia bone marrow Disc. AE
95 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 95 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 95 mg/m2, 1 times / day
Sources: Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.11
Gastrointestinal bleeding Disc. AE
95 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 95 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 95 mg/m2, 1 times / day
Sources: Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.11
Mucositis grade 4
Disc. AE
95 mg/m2 1 times / day multiple, intravenous
Overdose
Dose: 95 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 95 mg/m2, 1 times / day
Sources: Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.11
Anuria Disc. AE
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Hyperthermia Disc. AE
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Lactate dehydrogenase increased Disc. AE
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Lactic acidosis Disc. AE
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Multiple organ failure Disc. AE
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources: Page: p.11
unhealthy, 63
n = 1
Health Status: unhealthy
Condition: Breast cancer and liver metastasis
Age Group: 63
Sex: F
Population Size: 1
Sources: Page: p.11
Soft tissue necrosis severe
Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Leukopenia DLT, Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Neutropenia DLT, Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Acute promyelocytic leukemia Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Hyperuricemia Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Pulmonary embolism Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Thromboembolic event Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Thrombophlebitis Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Congestive heart failure grade 3-5
Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Myelosuppression severe
Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Toxic myocarditis severe
Disc. AE
120 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 120 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 120 mg/m2, 1 times / 3 weeks
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources: Page: p.1
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Docetaxel and epirubicin in advanced breast cancer.
2001
Adjuvant chemotherapy with high-dose cyclophosphamide, etoposide and cisplatin intensification without progenitor cell support in breast cancer patients with ten or more involved nodes: 5-year results of a pilot trial.
2001
Dose-dense sequential adjuvant chemotherapy with epirubicin, paclitaxel and CMF in high-risk breast cancer.
2001
Intensive cyclic chemotherapy with unprocessed whole blood support in advanced breast cancer.
2001
Chemotherapy of metastatic breast cancer: what to expect in 2001 and beyond.
2001
Dose-dense sequential chemotherapy with epirubicin and paclitaxel in advanced breast cancer.
2001
Adjuvant chemotherapy for gastro-oesophageal cancer with epirubicin, cisplatin and fluorouracil: a single-centre experience.
2001
Intensified chemotherapy supported by DMSO-free peripheral blood progenitor cells in breast cancer patients.
2001 Apr
Gemcitabine, epirubicin, and paclitaxel combinations in advanced breast cancer.
2001 Apr
Tolerability of the cytoprotective agent amifostine in elderly patients receiving chemotherapy: a comparative study.
2001 Apr
[Early phase II study of amrubicin (SM-5887) for superficial bladder cancer: a dose-finding study for intravesical chemotherapy].
2001 Apr
Second-line therapy for potentially platinum-sensitive recurrent ovarian cancer: what is optimal treatment?
2001 Apr
Local hyperthermia, radiation, and chemotherapy in recurrent breast cancer is feasible and effective except for inflammatory disease.
2001 Apr 1
Patterns of failure after induction chemotherapy and radiotherapy for locoregionally advanced nasopharyngeal carcinoma: the Queen Mary Hospital experience.
2001 Apr 1
Dose-dense sequential chemotherapy with epirubicin and paclitaxel versus the combination, as first-line chemotherapy, in advanced breast cancer: a randomized study conducted by the Hellenic Cooperative Oncology Group.
2001 Apr 15
Clinical and pharmacologic study of the epirubicin and paclitaxel combination in women with metastatic breast cancer.
2001 Apr 15
Accelerated-intensified cyclophosphamide, epirubicin, and fluorouracil (CEF) compared with standard CEF in metastatic breast cancer patients: results of a multicenter, randomized phase III study of the Italian Gruppo Oncologico Nord-Ouest-Mammella Inter Gruppo Group.
2001 Apr 15
Multimodality therapy for patients with clinical Stage I and II malignant mixed Müllerian tumors of the uterus.
2001 Apr 15
Neurophysiological evaluation of late effects of adjuvant high-dose chemotherapy on cognitive function.
2001 Jan
[Docetaxel (Taxotere) in combination with anthracycline, capecitabin (Xeloda) and new drugs].
2001 Jan-Feb
Impact of intravesical chemotherapy on recurrence rate of recurrent superficial transitional cell carcinoma of the bladder: results of a meta-analysis.
2001 Jan-Feb
Combined use of chemotherapy and 131I-metaiodobenzylguanidine in the treatment of advanced-stage neuroblastoma.
2001 Jan-Mar
Activation of caspase-3 in renal cell carcinoma cells by anthracyclines or 5-fluorouracil.
2001 Jul
Chemotherapy response of breast cancer depends on HER-2 status and anthracycline dose intensity in the neoadjuvant setting.
2001 Jun
Phase II study of epirubicin, mitomycin C, and 5-fluorouracil in hormone-refractory prostatic carcinoma.
2001 Jun
Results of a phase III prospective, randomised trial, comparing mitoxantrone and vinorelbine (MV) in combination with standard FAC/FEC in front-line therapy of metastatic breast cancer.
2001 Jun
Importance of surgery as salvage treatment after high dose chemotherapy failure in germ cell tumors.
2001 Jun
Phase III trial comparing two dose levels of epirubicin combined with cyclophosphamide with cyclophosphamide, methotrexate, and fluorouracil in node-positive breast cancer.
2001 Jun 15
Metastatic eccrine porocarcinoma: response to docetaxel (Taxotere) chemotherapy.
2001 Mar
Impact of chemotherapy dose-density on radiotherapy dose-intensity after breast conserving surgery.
2001 Mar
High incidence of central nervous system involvement in patients with metastatic or locally advanced breast cancer treated with epirubicin and docetaxel.
2001 Mar
A phase II study of dose-intense ifosfamide plus epirubicin with hematopoietic growth factors for the treatment of patients with advanced soft tissue sarcomas; a novel sequential schedule.
2001 Mar
Docetaxel and epirubicin plus G-CSF as mobilizing treatment to support high-dose chemotherapy in breast cancer.
2001 Mar-Apr
Prophylactic chemolipiodolization for postoperative hepatoma patients.
2001 Mar-Apr
Neoadjuvant high dose chemotherapy plus peripheral blood progenitor cells in inflammatory breast cancer: a multicenter phase II pilot study.
2001 May
Optimizing adjuvant breast cancer chemotherapy: rationale for the MA.21 study.
2001 May
New combinations with epirubicin in advanced breast cancer.
2001 May
Epirubicin/taxane combinations in breast cancer: experience from several Italian trials.
2001 May
Dose-dense and sequential strategies in adjuvant breast cancer therapy.
2001 May
Body surface area as a determinant of pharmacokinetics and drug dosing.
2001 May
Neoadjuvant chemotherapy for Chinese women with locally advanced breast cancer.
2001 May
Management of extravasation injuries.
2001 May
Kinetics of PBPC mobilization by cyclophosphamide, as compared with that by epirubicin/paclitaxel followed by G-CSF support: implications for optimal timing of PBPC harvest.
2001 May
Peripheral blood progenitor cell collection after epirubicin, paclitaxel, and cisplatin combination chemotherapy using EPO-based cytokine regimens: a randomized comparison of G-CSF and sequential GM-/G-CSF.
2001 May
The multimodality treatment of thymic carcinoma.
2001 May
Analysis of treatment failures and survival of patients with fallopian tube carcinoma: a cooperation task force (CTF) study.
2001 May
Standard chemotherapy for gastric carcinoma: is it a myth?
2001 May 15
Prospective evaluation of early cardiac damage induced by epirubicin-containing adjuvant chemotherapy and locoregional radiotherapy in breast cancer patients.
2001 May 15
Definitive results of a phase II trial of cisplatin, epirubicin, continuous-infusion fluorouracil, and gemcitabine in stage IV pancreatic adenocarcinoma.
2001 May 15
Telomere length in breast cancer patients before and after chemotherapy with or without stem cell transplantation.
2001 May 18
Patents

Sample Use Guides

Injection is administered to patients by intravenous infusion. Drug is given in 14 repeated 3- to 4-week cycles. The total dose may be given on Day 1 of each cycle 15 or divided equally and given on Days 1 and 8 of each cycle. The recommended starting dose is 100 to 120 mg/m2.
Route of Administration: Intravenous
It was investigated the effect of combined treatment with the anthracycline agent epirubicin (EPI) and NK cells on human breast cancer cells. NK cells were obtained by autologous adoptive cell transfer from breast cancer patients and amplified for 14 days in vitro. The cytotoxicity of NK cells against breast cancer cells was higher following EPI (5.0 μg/ml) pretreatment than without EPI pretreatment or application of EPI alone. The expression of NKG2D ligands [unique long 16-binding protein (ULBP) 1, ULBP2, and major histocompatibility complex class I-related chain A] in breast cancer cells was upregulated by pretreatment with EPI, which also increased the secretion of interferon-γ and tumor necrosis factor-α and expression of perforin and granzyme B in NK cells. These results indicate that EPI-NK cell treatment has synergistic cytotoxic effects against breast cancer cells, and suggest that anthracycline-based chemotherapy and NK cell-based immunotherapy can be combined for more effective breast cancer treatment.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:17:22 UTC 2021
Edited
by admin
on Sat Jun 26 16:17:22 UTC 2021
Record UNII
3Z8479ZZ5X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIRUBICIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
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)-
Common Name English
EPIADRIAMYCIN
Common Name English
EPIDOXORUBICIN
Common Name English
(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
Common Name English
EPIRUBICIN [HSDB]
Common Name English
4'-EPI-ADRIAMYCIN
Common Name English
EPIRUBICINE
Common Name English
EPIRUBICIN [VANDF]
Common Name English
NSC-256942
Code English
EPIRUBICIN [WHO-DD]
Common Name English
FARMORUBICIN
Brand Name English
EPIRUBICIN [MI]
Common Name English
EPIRUBICIN [INN]
Common Name English
Classification Tree Code System Code
LIVERTOX 356
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NDF-RT N0000000176
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NDF-RT N0000007530
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
FDA ORPHAN DRUG 588517
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
WHO-ATC L01DB03
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NDF-RT N0000175414
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
FDA ORPHAN DRUG 121498
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
WHO-VATC QL01DB03
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NCI_THESAURUS C1594
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NDF-RT N0000007530
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
NDF-RT N0000007530
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
Code System Code Type Description
INN
5171
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
EVMPD
SUB06571MIG
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
RXCUI
3995
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY RxNorm
MESH
D015251
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
CAS
56420-45-2
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
HSDB
6962
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
MERCK INDEX
M4948
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY Merck Index
FDA UNII
3Z8479ZZ5X
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
EPA CompTox
56420-45-2
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
NCI_THESAURUS
C62028
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
WIKIPEDIA
EPIRUBICIN
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
DRUG CENTRAL
1030
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
DRUG BANK
DB00445
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
PUBCHEM
41867
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL417
Created by admin on Sat Jun 26 16:17:23 UTC 2021 , Edited by admin on Sat Jun 26 16:17:23 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
The mean metabolite/parent AUC ratio is about 25% for 7-deoxydoxorubicin aglycone
METABOLITE -> PARENT
The mean metabolite/parent AUC ratio is about 15% for doxorubicin aglycone
METABOLITE -> PARENT
The mean metabolite/parent AUC ratio is about 15% for doxorubicinol aglycone
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC