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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.COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@@H](O)[C@H](C)O5)C(=O)CO)C(O)=C3C(=O)C2=CC=C1

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
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
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

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
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
High-dose epirubicin plus docetaxel at standard dose with lenograstim support as first-line therapy in advanced breast cancer.
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
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
Treatment of classical type Kaposi's sarcoma with paclitaxel.
2001 Jan-Feb
Reversal of multidrug resistance to epirubicin by cyclosporin A in liposomes or intralipid.
2001 Jan-Feb
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
Effective treatment with rituximab in a patient with refractory prolymphocytoid transformed B-chronic lymphocytic leukemia and Evans syndrome.
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
Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7.
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

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 Tue Oct 22 00:23:32 UTC 2019
Edited
by admin
on Tue Oct 22 00:23:32 UTC 2019
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 [USP]
Common Name English
WP-697
Code English
EPIRUBICIN HCL
VANDF  
Common Name English
EPIRUBICIN HYDROCHLORIDE [WHO-DD]
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]
Common Name English
EPIRUBICIN HYDROCHLORIDE [USAN]
Common Name English
EPIRUBICIN HYDROCHLORIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C474
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY
ChEMBL
CHEMBL417
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY
ECHA (EC/EINECS)
260-145-2
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY
RXCUI
203213
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY RxNorm
CAS
56390-09-1
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY
MERCK INDEX
M4948
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY Merck Index
EVMPD
SUB01915MIG
Created by admin on Tue Oct 22 00:23:32 UTC 2019 , Edited by admin on Tue Oct 22 00:23:32 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY