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E9406

Epirubicin hydrochloride

≥90% (HPLC)

Synonym(s):

4′-Epidoxorubicin hydrochloride, Epidoxorubicin hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
56390-09-1
Molecular Weight:
579.98
NACRES:
NA.85
PubChem Substance ID:
329799084
UNSPSC Code:
51102829
EC Number:
260-145-2
MDL number:
MFCD00941448

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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

InChI key

MWWSFMDVAYGXBV-FGBSZODSSA-N

SMILES string

Cl.COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO

biological source

synthetic

assay

≥90% (HPLC)

form

powder

color

red to deep red

solubility

H2O: soluble

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

−20°C

Quality Level

100

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Show Differences

1 of 4

This Item
PZ036244583P3246
Epirubicin hydrochloride ≥90% (HPLC)

Sigma-Aldrich

E9406

Epirubicin hydrochloride

CP-640186 hydrochloride ≥95% (HPLC)

Sigma-Aldrich

PZ0362

CP-640186 hydrochloride

Doxorubicin hydrochloride suitable for fluorescence, 98.0-102.0% (HPLC)

Sigma-Aldrich

44583

Doxorubicin hydrochloride

Pipamperone dihydrochloride ~99% (HPLC), powder

Sigma-Aldrich

P3246

Pipamperone dihydrochloride

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

form

powder

form

powder

form

solid

form

powder

assay

≥90% (HPLC)

assay

≥95% (HPLC)

assay

98.0-102.0% (HPLC)

assay

~99% (HPLC)

solubility

H2O: soluble

solubility

H2O: 2 mg/mL, clear (warmed)

solubility

H2O: 50 mg/mL, clear, orange to red, DMSO: soluble, THF: soluble, ethanol: soluble, methanol: soluble

solubility

H2O: >2.0 mg/mL

Application

Epirubicin is used to inhibit topoisomerase II and DNA helicase activity. Epirubicin is used to study metastatic breast cancer[1]and cardiac toxicity[2].

Biochem/physiol Actions

Cell-permeable anthracycline antitumor antibiotic. Antineoplastic. A stereoisomer of doxorubicin that exhibits reduced cardiotoxicity. Its antitumor actions are mediated by targeting topoisomerase II.
Epirubicin is antimitotic and cytotoxic. It inhibits nucleic acid and protein synthesis. Epirubicin may do so by forming complexes with DNA and intercalation between base pairs, by inhibiting topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, and by preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Muta. 1B - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000496920
0000496928
0000496928
0000496920
0000473741

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O Feher et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 16(6), 899-908 (2005-04-12)
This randomized, phase III study compared the efficacy and safety of first-line gemcitabine versus epirubicin in the treatment of postmenopausal women with metastatic breast cancer (MBC). Patients aged > or = 60 years (median 68 years) with clinically measurable MBC
Letícia Tiburcio Ferreira et al.
Antimicrobial agents and chemotherapy, 64(9) (2020-07-01)
Widespread resistance against antimalarial drugs thwarts current efforts for controlling the disease and urges the discovery of new effective treatments. Drug repositioning is increasingly becoming an attractive strategy since it can reduce costs, risks, and time-to-market. Herein, we have used
Aman U Buzdar et al.
The Lancet. Oncology, 14(13), 1317-1325 (2013-11-19)
Neoadjuvant chemotherapy with trastuzumab for patients with HER2-positive breast cancer can produce a pathological complete response in the breast in 30-65% of patients. We investigated the effect of the timing of trastuzumab administration with anthracycline and taxane neoadjuvant chemotherapy. This
Tobias Arnold et al.
European journal of clinical investigation, 43(3), 286-291 (2013-02-16)
The response of breast cancer patients to neoadjuvant chemotherapy (NCT) is highly heterogeneous, and reliable predictive instruments remain to be defined. High-mobility group box-1 (HMGB-1) protein is a cell death marker, which is easily detectable in plasma. We hypothesized that
P Fumoleau et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 17(1), 85-92 (2005-10-28)
The aim of the study was to evaluate and compare incidence and risk factors of left ventricular dysfunction (LVD) in early breast cancer patients receiving (E+) or not (E-) epirubicin-based adjuvant chemotherapy. Among eight FASG trials, 3577 assessable patients were
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