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E9406

Sigma-Aldrich

Epirubicin hydrochloride

≥90% (HPLC)

Synonyme(s) :

4′-Epidoxorubicin hydrochloride, Epidoxorubicin hydrochloride

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About This Item

Formule empirique (notation de Hill):
C27H29NO11 · HCl
Numéro CAS:
56390-09-1
Poids moléculaire :
579.98
Numéro CE :
260-145-2
Numéro MDL:
MFCD00941448
Code UNSPSC :
51102829
ID de substance PubChem :
329799084
Nomenclature NACRES :
NA.85

Source biologique

synthetic

Niveau de qualité

100

Pureté

≥90% (HPLC)

Forme

powder

Couleur

red to deep red

Solubilité

H2O: soluble

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

DNA synthesis | interferes
enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H340,H350,H360

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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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
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
D Groheux et al.
British journal of cancer, 109(5), 1157-1164 (2013-08-15)
Pathologic complete response (pCR) to neoadjuvant treatment (NAT) is associated with improved survival of patients with HER2+ breast cancer. We investigated the ability of interim positron emission tomography (PET) regarding early prediction of pathology outcomes. During 61 months, consecutive patients
Sarah N Hamilton et al.
International journal of radiation oncology, biology, physics, 87(4), 719-725 (2013-09-05)
To review the treatment and outcomes of patients with primary cutaneous B-cell lymphoma (CBCL). Clinical characteristics, treatment, and outcomes were analyzed for all patients referred to our institution from 1981 through 2011 with primary CBCL without extracutaneous or distant nodal
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