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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO11.ClH
Molecular Weight 579.98
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIRUBICIN HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(C[C@H](N)[C@@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)CO

InChI

InChIKey=MWWSFMDVAYGXBV-FGBSZODSSA-N
InChI=1S/C27H29NO11.ClH/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;1H/t10-,13-,15-,17-,22-,27-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C27H29NO11
Molecular Weight 543.5193
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

CNS Non-penetrant
1018

Originator

Approval Year

1999
156
Targets

Targets

Primary TargetPharmacologyConditionPotency
Crosslinking Agent
77
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050807lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
Disc. AE: Aplasia bone marrow, Mucositis...
AEs leading to
discontinuation/dose reduction:
Aplasia bone marrow
Mucositis (grade 4)
Gastrointestinal bleeding
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
320 mg/m2 single, intravenous
Overdose
Dose: 320 mg/m2
Route: intravenous
Route: single
Dose: 320 mg/m2
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
Disc. AE: Soft tissue necrosis...
AEs leading to
discontinuation/dose reduction:
Soft tissue necrosis (severe)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://pubmed.ncbi.nlm.nih.gov/10394119
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.11
unhealthy, 36
n = 1
Health Status: unhealthy
Condition: non-Hodgkin’s lymphoma
Age Group: 36
Sex: M
Population Size: 1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Axillary node tumor involvement following resection of primary breast cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050778s021lbl.pdf
Page: p.1
Sourcing

Sourcing

Vendor/AggregatorIDURL
AA Blocks
AA00I9ZQ
https://www.aablocks.com/goods/Goods/detail?id=AA00I9ZQ
Achemtek
0104-013942
http://www.achemtek.com/56420-45-2
Acorn PharmaTech
ACN-038342
http://www.acornpharmatech.com/
Adooq BioScience
A12409
https://www.adooq.com/epirubicin.html
Alsachim
4680
http://www.alsachim.com/product-C6028-glo.bal-view.html
Ambinter
Amb21856008
http://www.ambinter.com/reference/21856008
Angene
AGN-PC-0WHA6U
http://www.angenechemical.com/productshow/AGN-PC-0WHA6U.html
AvaChem Scientific
2020B
http://www.avachem.com/productSearch.asp?2020B
Chem Scene
CS-2824
http://www.chemscene.com/56420-45-2.html
ChemMol
49424940
http://www.chemmol.com/chemmol/49424940.html
Lab Network
LN01341812
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341812
MedChem Express
HY-13624
https://www.medchemexpress.com/epirubicin.html
MuseChem
I004109
https://www.musechem.com/product/I004109.html
Parchem
28852
http://www.parchem.com/chemical-supplier-distributor/Epirubicin-018852.aspx
Smolecule
S527283
http://www.smolecule.com/products/s527283
THE BioTek
bt-267488
https://www.thebiotek.com/product/inhibitors/bt-267488
THE BioTek
bt-288837
https://www.thebiotek.com/product/others/bt-288837
Vesino Industrial Co Ltd
VA10821
http://www.vsnchem.com/goto/product/23243/
eNovation Chemicals
D681979
https://www.enovationchem.com/ProductDetails.asp?ProductID=D681979
iChemical
EBD2199801
http://www.ichemical.com/products/56420-45-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
Epirubicin for adjuvant therapy in node-positive breast cancer.
2000 Feb 7
Single agent epirubicin as first line chemotherapy for metastatic breast cancer patients.
2000 Jan
Docetaxel and epirubicin in advanced breast cancer.
2001
Intensive cyclic chemotherapy with unprocessed whole blood support in advanced breast cancer.
2001
Dose-dense sequential chemotherapy with epirubicin and paclitaxel in advanced breast cancer.
2001
Complete cure of malignant lymphoma of the stomach with a huge adrenal lesion achieved by preoperative chemotherapy and surgery: report of a case.
2001
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
Clinical impacts of tumor cell contamination of hematopoietic stem cell products in metastatic breast cancer patients undergoing autologous peripheral blood stem cell transplantation: multicenter trial.
2001 Apr
Primary high-grade mucosa-associated lymphoid tissue-type lymphoma of the cervix presenting as a common endocervical polyp.
2001 Apr
Expression and prognostic significance of catalase in malignant mesothelioma.
2001 Apr 1
Multimodality therapy for patients with clinical Stage I and II malignant mixed Müllerian tumors of the uterus.
2001 Apr 15
A phase II study of sequential chemotherapy with docetaxel after the weekly PELF regimen in advanced gastric cancer. A report from the Italian group for the study of digestive tract cancer.
2001 Feb
Interferon alfa 2b as maintenance therapy in poor risk diffuse large B-cell lymphoma in complete remission after intensive CHOP-BLEO regimens.
2001 Feb
Thymidine kinase and thymidylate synthase in advanced breast cancer: response to tamoxifen and chemotherapy.
2001 Feb 15
Generalised seizures following ondansetron.
2001 Jan
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
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
Adjuvant chemotherapy for adult soft tissue sarcomas of the extremities and girdles: results of the Italian randomized cooperative trial.
2001 Mar 1
Optimizing adjuvant breast cancer chemotherapy: rationale for the MA.21 study.
2001 May
Neoadjuvant chemotherapy for Chinese women with locally advanced breast cancer.
2001 May
Management of extravasation injuries.
2001 May
Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7.
2001 May
Patents

Patents

20010004454
39
20010016196
11
JP2006502184A
40
JP2008533019A
33
JP2009531296A
20
JP2011501962A
9
JP2011528275A
445
JP2012500104A
107
JPH10175991A
3

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Fri Dec 16 17:21:54 UTC 2022
Edited
by admin
on Fri Dec 16 17:21:54 UTC 2022
Record UNII
22966TX7J5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIRUBICIN HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
EPIRUBICIN HYDROCHLORIDE [MI]
Common Name English
EPIRUBICIN HCL [VANDF]
Common Name English
ELLENCE
Brand Name English
FARMORUBICINA
Brand 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 HYDROCHLORIDE
Common Name English
Epirubicin hydrochloride [WHO-DD]
Common Name English
WP-697
Code English
EPIRUBICIN HCL
VANDF  
Common Name English
EPIRUBICIN HYDROCHLORIDE [JAN]
Common Name English
EPIRUBICIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
EPIRUBICIN HYDROCHLORIDE [MART.]
Common Name English
EPIRUBICIN HYDROCHLORIDE [ORANGE BOOK]
Common 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-, HYDROCHLORIDE, (8S-CIS)-
Common Name English
IMI-28
Code English
EPIRUBICIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
EPIRUBICIN HYDROCHLORIDE [USAN]
Common Name English
EPIRUBICIN HYDROCHLORIDE [USP-RS]
Common Name English
NSC-759195
Code English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
Code System Code Type Description
DRUG BANK
DBSALT001168
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
NCI_THESAURUS
C474
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
NSC
759195
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
DAILYMED
22966TX7J5
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
ChEMBL
CHEMBL417
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
ECHA (EC/EINECS)
260-145-2
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
FDA UNII
22966TX7J5
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
EPA CompTox
DTXSID50860297
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
RXCUI
203213
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY RxNorm
CAS
56390-09-1
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
MERCK INDEX
M4948
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY Merck Index
PUBCHEM
65348
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
USAN
W-74
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
EVMPD
SUB01915MIG
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
RS_ITEM_NUM
1237382
Created by admin on Fri Dec 16 17:21:54 UTC 2022 , Edited by admin on Fri Dec 16 17:21:54 UTC 2022
PRIMARY
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Structure of EPIRUBICIN HYDROCHLORIDE
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ASSAY (HPLC)
EP
Structure of EPIRUBICIN
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Structure of EPIRUBICIN HYDROCHLORIDE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
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Structure of EPIRUBICIN DIMER
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