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E9406

Sigma-Aldrich

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
EC Number:
260-145-2
MDL number:
MFCD00941448
UNSPSC Code:
51102829
PubChem Substance ID:
329799084
NACRES:
NA.85

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

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

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

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Application

Epirubicin is used to inhibit topoisomerase II and DNA helicase activity. Epirubicin is used to study metastatic breast cancerand cardiac toxicity.

Biochem/physiol Actions

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.
Cell-permeable anthracycline antitumor antibiotic. Antineoplastic. A stereoisomer of doxorubicin that exhibits reduced cardiotoxicity. Its antitumor actions are mediated by targeting topoisomerase II.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H340,H350,H360

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
Nuno Figueiredo et al.
Immunity, 39(5), 874-884 (2013-11-05)
Severe sepsis remains a poorly understood systemic inflammatory condition with high mortality rates and limited therapeutic options in addition to organ support measures. Here we show that the clinically approved group of anthracyclines acts therapeutically at a low dose regimen
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