ChemicalBook > CAS DataBase List > Epirubicin hydrochloride

Epirubicin hydrochloride

Product Name
Epirubicin hydrochloride
CAS No.
56390-09-1
Chemical Name
Epirubicin hydrochloride
Synonyms
Ebewe;Adrial;CS-1396;Ellence;Epirubin HCI;Epirubicin Ebewe;Farmorubicin-RTU;(8s-cis)-rochlorid;EpirubicinHc,LEp5,;Epirubicin HCl API
CBNumber
CB3501568
Molecular Formula
C27H30ClNO11
Formula Weight
579.9802
MOL File
56390-09-1.mol
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Epirubicin hydrochloride Property

Melting point:
185°C dec.
alpha 
D20 +274° (c = 0.01 in methanol)
RTECS 
QI9295750
Flash point:
443.8℃
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in DMSO to 100mM, or in ethanol to 10mM
form 
powder
color 
red to deep red
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
InChIKey
MWWSFMDVAYGXBV-UAOJCOQHSA-N
SMILES
C12=C(O)C3=C(C(=O)C4=C(C3=O)C=CC=C4OC)C(O)=C1[C@@]([H])(O[C@H]1O[C@@H](C)[C@H](O)[C@@H](N)C1)C[C@](O)(C(=O)CO)C2.Cl
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Safety

Hazard Codes 
Xn
Risk Statements 
22-63-62-46-40
Safety Statements 
36/37/38-45-46
WGK Germany 
3
HS Code 
29419090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H340May cause genetic defects

H350May cause cancer

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E9406
Product name
Epirubicin hydrochloride
Purity
≥90% (HPLC)
Packaging
5mg
Price
$217
Updated
2024/03/01
Sigma-Aldrich
Product number
BP992
Product name
Epirubicin hydrochloride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$208
Updated
2024/03/01
Sigma-Aldrich
Product number
1237382
Product name
Epirubicin hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$1340
Updated
2024/03/01
Alfa Aesar
Product number
J60411
Product name
Epirubicin hydrochloride
Packaging
10mg
Price
$244
Updated
2024/03/01
Alfa Aesar
Product number
J60411
Product name
Epirubicin hydrochloride
Packaging
100mg
Price
$944
Updated
2024/03/01
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Epirubicin hydrochloride Chemical Properties,Usage,Production

Description

Epirubicin hydrochloride is an antitumor antibiotic which is epimeric with doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas, as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is reported to be less sardiotoxic than doxorubicin.

Description

Epirubicin is a stereoisomer of the antitumor anthracycline doxorubicin that undergoes β-glucuronidation, which partially detoxifies the dose-limiting side effects that are present with doxorubicin. Compared to doxorubicin, epirubicin is equally cytotoxic to HeLa cells (ID50s = 9 μM). When used either alone or in combination therapies, epirubicin has been shown to demonstrate high rates of complete or partial remission in various cancers including advanced ovary, lymphomas, breast, pancreas, gastric, hepatocellular carcinoma, head and neck tumors, and colorectal.

Chemical Properties

Orange-Red Crystalline Solid

Originator

Erbamont (Italy)

Uses

Used as an antineoplastic

Uses

Cell-permeable anthracycline anti-tumor antibiotic

brand name

Ellence(Pfizer);FARMORUBICIN.

Biological Functions

This stereoisomer of doxorubicin has the 4′-hydroxy group of the daunosamine sugar oriented in the β-position . Epirubicin will be slowly reduced to the active C13 alcohol (epirubicinol), giving it a 30- to 38-hour half life, which is similar to that of doxorubicin. Unlike doxorubicinol, however, which was equally active with doxorubicin, epirubicinol has only one-tenth the activity of its parent drug and is not believed to contribute significantly to the therapeutic action of this agent.

Biological Activity

Antibiotic antitumor agent. Inhibits the synthesis and function of DNA (IC 50 = 62.7 μ M in rat glioblastoma cell lines) and inhibits the relaxing property of topoisomerase II.

Clinical Use

Epirubicin is indicated for use in breast cancer, and the starting dose is 100 to 120 mg/m2 (compared to a starting dose of 60–75 mg/m2 for doxorubicin).

Side effects

The side effects and precautions are as outlined previously for doxorubicin, although there is a lower risk of serious myocardial toxicity or myelotoxicity.

Drug interactions

Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine - increased risk of agranulocytosis.
Ciclosporin: increased risk of neurotoxicity
Cytotoxics: possible increased risk of cardiotoxicity with trastuzumab - avoid for up to 28 weeks after stopping trastuzumab.
Ulcer-healing drugs: concentration increased by cimetidine.
Vaccines: avoid with live vaccines

Metabolism

Cleavage of the epimerized sugar will occur before excretion, generating an aglycone that is indistinguishable from that generated by doxorubicin. Although excretion is primarily biliary, dosage reduction in severe renal impairment, as well as in hepatic dysfunction, is warranted.

storage

+4°C

References

1) Cersosimo?et al. (1986),?Epirubicin: a review of the pharmacology, clinical activity, and adverse effects of an adriamycin analogue; J. Clin. Oncol.,?4?425 2) Spadari?et al. (1986),?DNA polymerases and DNA topoisomerases as targets for the development of anticancer drugs; Anticancer Res.,?6?935 3) Minotti?et al. (2004),?Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity; Pharmacol. Rev.,?56?185 4) Mercuro?et al. (2007),?Early epirubicin-induced myocardial dysfunction revealed by serial tissue Doppler echocardiography: correlation with inflammatory and oxidative stress markers; Oncologist,?12?1124

Epirubicin hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Epirubicin hydrochloride Suppliers

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View Lastest Price from Epirubicin hydrochloride manufacturers

Hebei Kangcang new material Technology Co., LTD
Product
Epirubicin hydrochloride 56390-09-1
Price
US $20.00-10.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20
Release date
2024-03-20
Hebei Kangcang new material Technology Co., LTD
Product
Epirubicin hydrochloride 56390-09-1
Price
US $9.00-60.00/g
Min. Order
10g
Purity
min99%
Supply Ability
10 tons
Release date
2024-03-22
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Epirubicin hydrochloride 56390-09-1
Price
US $0.00/g/Bag
Min. Order
1g
Purity
98%min
Supply Ability
1000g
Release date
2021-10-18

56390-09-1, Epirubicin hydrochlorideRelated Search:

6-Aminocaproic acid Doxorubicin hydrochloride Tris(hydroxymethyl)aminomethane Epirubicin Glycine 3-Aminophenol Acetaminophen EC 2.6.1.2 Topotecan hydrochloride 1-AdaMantanethylaMine Aminopyrine Centchroman Tetrahydro-4H-pyran-4-one ALTRENOGEST Glucosamine Doxycycline hydrochloride Enrofloxacin hydrochloride Benzydamine hydrochloride

  • CS-1396
  • Epirubicin hydrochloride, ≥90% (HPLC)
  • Epirubicin Hydrochloride - CAS 56390-09-1 - Calbiochem
  • epi-Doxorubicin HCl
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  • ELLENCE; PHARMORUBICIN; EPIRUBICIN EBEWE
  • Epirubicin Ebewe
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  • Epirubicin HCl Epirubicin hydrochloride
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  • 8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-l)oxy)-hyd
  • EPIRUBICIN HYDROCHLORIDE EP STANDARD
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  • 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, hydrochloride (1:1), (8S,10S)-
  • (8S,10S)-10-(((2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-tri
  • Ellence, Farmorubicin, Pharmorubicin
  • 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,10S)-
  • 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-
  • 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-
  • Epidoxorubicin hydrochloride
  • (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride
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  • (8S-cis)-4'-Epidoxorubicin Hydrochloride
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  • (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedionehydrochloride
  • Epirubin HCI
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  • (8S,10S)-10-(((2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
  • Epirubicin hydrochloride USP/EP/BP
  • cis)-10-[(3-Amino-2,3,6-tridesoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacen-5,12-dionhydrochlorid
  • Epirubicin hydrochloride / Epirubicin hcl
  • 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, hydrochloride (1:1), (8S,10S)-
  • (8R,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-7-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
  • Epirubicin HydrochlorideQ: What is Epirubicin Hydrochloride Q: What is the CAS Number of Epirubicin Hydrochloride Q: What is the storage condition of Epirubicin Hydrochloride Q: What are the applications of Epirubicin Hydrochloride
  • Epirubicin Hydrochloride (EPR.HCl), 97%
  • Epirubicin Hydrochloride (1237382)
  • (8S,10S)-10-(((2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride (Doxorubicin Impurity)
  • Ebewe
  • Epirubicin (IMI 28) HCl
  • (8R,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-7-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,1
  • 56390-09-1
  • C27H28NO11xHCl
  • C27H34ClNO11
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  • 57998
  • 11
  • Anti-cancer&immunity
  • API
  • Antineoplastic