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Epirubicin hydrochloride

Name: Epirubicin hydrochloride
Brand: SIGMA

≥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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Properties

biological source

synthetic

Quality Segment

100

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

Description

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.

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This Item	PZ0362	44583	P3246
Sigma-Aldrich E9406 Epirubicin hydrochloride	Sigma-Aldrich PZ0362 CP-640186 hydrochloride	Sigma-Aldrich 44583 Doxorubicin hydrochloride	Sigma-Aldrich P3246 Pipamperone dihydrochloride
antibiotic activity spectrum neoplastics	antibiotic activity spectrum -	antibiotic activity spectrum neoplastics	antibiotic activity spectrum -
mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action -	mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action -
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 100
assay ≥90% (HPLC)	assay ≥95% (HPLC)	assay 98.0-102.0% (HPLC)	assay ~99% (HPLC)
form powder	form powder	form solid	form powder
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