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Epirubicin hydrochloride

CAS No.
56390-09-1
Chemical Name:
Epirubicin hydrochloride
Synonyms
Ebewe;Adrial;Ellence;CS-1396;Epirubin HCI;Farmorubicin-RTU;Epirubicin Ebewe;EpirubicinHc,LEp5,;Epirubicin HCl API;(8s-cis)-rochlorid
CBNumber:
CB3501568
Molecular Formula:
C27H30ClNO11
Molecular Weight:
579.9802
MDL Number:
MFCD00274554
MOL File:
56390-09-1.mol
Last updated:2024-11-19 23:02:33

Epirubicin hydrochloride Properties

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
NCI Dictionary of Cancer Terms Ellence; epirubicin hydrochloride
FDA UNII 22966TX7J5
NCI Drug Dictionary Ellence

Pharmacokinetic data

Protein binding 77%
Excreted unchanged in urine 9-10%
Volume of distribution 14-38
Biological half-life 30-40 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H340-H350-H360
Precautionary statements  P201-P301+P312+P330-P308+P313
Hazard Codes  Xn
Risk Statements  22-63-62-46-40
Safety Statements  36/37/38-45-46
WGK Germany  3
HS Code  29419090
NFPA 704
0
2 0

Epirubicin hydrochloride price More Price(62)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E9406 Epirubicin hydrochloride ≥90% (HPLC) 56390-09-1 5mg $217 2024-03-01 Buy
Sigma-Aldrich BP992 Epirubicin hydrochloride British Pharmacopoeia (BP) Reference Standard 56390-09-1 100MG $208 2024-03-01 Buy
Sigma-Aldrich 1237382 Epirubicin hydrochloride United States Pharmacopeia (USP) Reference Standard 56390-09-1 200mg $1340 2024-03-01 Buy
Alfa Aesar J60411 Epirubicin hydrochloride 56390-09-1 10mg $244 2024-03-01 Buy
Alfa Aesar J60411 Epirubicin hydrochloride 56390-09-1 100mg $944 2024-03-01 Buy
Product number Packaging Price Buy
E9406 5mg $217 Buy
BP992 100MG $208 Buy
1237382 200mg $1340 Buy
J60411 10mg $244 Buy
J60411 100mg $944 Buy

Epirubicin hydrochloride Chemical Properties,Uses,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

Cell-permeable anthracycline anti-tumor antibiotic

Uses

Used as an antineoplastic

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

Global( 426)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Kangcang new material Technology Co., LTD
+8615713292910 Nancy@kangcang.com.cn China 341 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8810 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12839 58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
+86-18600796368 +86-18600796368 sales@sjar-tech.com China 444 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32957 60
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29881 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2930 58
Biochempartner
0086-13720134139 candy@biochempartner.com CHINA 965 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28172 58

View Lastest Price from Epirubicin hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Epirubicin hydrochloride pictures 2024-11-27 Epirubicin hydrochloride
56390-09-1
US $0.00 / g/Bag 1g 98%min 1000g WUHAN FORTUNA CHEMICAL CO., LTD
Epirubicin hydrochloride pictures 2024-11-19 Epirubicin hydrochloride
56390-09-1
US $33.00-81.00 / mg 99.79% 10g TargetMol Chemicals Inc.
Epirubicin hydrochloride pictures 2024-11-19 Epirubicin hydrochloride
56390-09-1
US $33.00-81.00 / mg 99.79% 10g TargetMol Chemicals Inc.

Epirubicin hydrochloride Spectrum

4’-epi-adriamycinhydrochloride 5,12-naphthacenedione,10-((3-amino-2,3,6-trideoxy-alpha-l-arabino-hexopyranosy 8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-l)oxy)-hyd EPIRUBICIN HYDROCHLORIDE EP STANDARD EpirubicinHc,LEp5, Adrial (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-naphthacenedione, hydrochloride (1:1) 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 Epirubicin hydrochloride Farmorubicin-RTU Epirubicin hydrochloride(4'-Epidoxorubicin) Ellence Epirubicin, Hydrochloride Salt Epirubicin Hydrochloride (200 mg) (8S-cis)-4'-Epidoxorubicin Hydrochloride Epirubicin HCl API (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 Epirubicin hydrochloride, >=99% Epirubicin HCl Epirubicin hydrochloride (8s-cis)-rochlorid Epirubicin hydrochloride CRS (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 (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 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)- Epirubicin Hydrochloride (EPR.HCl), 97% Epirubicin Hydrochloride (1237382) CS-1396 Epirubicin hydrochloride, ≥90% (HPLC) Epirubicin Hydrochloride - CAS 56390-09-1 - Calbiochem epi-Doxorubicin HCl Epirubicin HCl (4'-epidoxorubicin) ELLENCE; PHARMORUBICIN; EPIRUBICIN EBEWE Epirubicin Ebewe (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 Epirubiein Hydrochloride 56390-09-1 C27H28NO11xHCl C27H34ClNO11 C27H33NO11 57998 Anti-cancer&immunity API Antineoplastic