Epirubicin hydrochloride

Modify Date: 2024-01-02 15:11:07

Epirubicin hydrochloride structure	Common Name	Epirubicin hydrochloride
	CAS Number	56390-09-1	Molecular Weight	579.980
	Density	1.61g/cm3	Boiling Point	810.3ºC at 760 mmHg
	Molecular Formula	C₂₇H₃₀ClNO₁₁	Melting Point	185ºC dec
	MSDS	N/A	Flash Point	443.8ºC
	Symbol	GHS07, GHS08	Signal Word	Danger

Use of Epirubicin hydrochloride

Epirubicin (hydrochloride) is a semisynthetic L-arabino derivative of doxorubicin, and an antineoplastic agent by inhibiting Topoisomerase.

Name	Epirubicin hydrochloride
Synonym	More Synonyms

Description	Epirubicin (hydrochloride) is a semisynthetic L-arabino derivative of doxorubicin, and an antineoplastic agent by inhibiting Topoisomerase.
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer
Target	Topoisomerase
In Vitro	Epirubicin, like doxorubicin, exerts its antitumor effects by complex with DNA, resulting in damage to DNA and interference with the synthesis of DNA, RNA, and proteins. Epirubicin may also affect the integrity and activity of cellular membranes. Maximal cell kill caused by Epirubicin occurs during the S phase of the cell cycle. With higher concentrations effects are also seen in early G2 as well as G1 and M phases[1]. Epirubicin display antineoplastic activity against most cancer cells. Epirubicin is cytotoxic to Hepatoma G2 cells with IC50 of 1.6 μg/mL at 24 hr. 1.6 μg/mL Epirubicin induces apoptosis of Hep G2 cells, and higher activity of catalase by 50%, Se-dependent glutathione peroxidase by 110%, Cu, Zn-superoxide dismutase by 172% and Mn-superoxide dismutase by 135%. Epirbicin increases the cellular expression of NADPH-CYP 450 reductase, and reduces GST-π expression[2].
In Vivo	Epirubicin are clinically active against a broad range of tumor types, including breast cancer, malignant lymphomas, soft tissue sarcomas, lung cancer, pleural mesothelioma, gastrointestinal cancer, head and neck cancer, ovarian cancer, prostatic carcinoma, transitional bladder carcinoma and so on[3]. Epirubicin at a dose of 3.5 mg/kg suppresses tumor mass of human breast tumor xenograft R-27 by 74.4 %[4].
Cell Assay	Hep G2 cells (500 cells/well, monolayer) are plated in a 96-well plate. The next day the cells are treated with Epirubicin in the medium. At the end of the incubation periods, 15% volume of MTT dye solution is added. After 1 hr of incubation at 37°C, an equal volume of solubilization/stop solution (dimethylsul-foxide) is added to each well for an additional 1 hr incubation. The absorbance of the reaction solution at 570 nm is recorded.
References	[1]. Cersosimo RJ, et al. Epirubicin: a review of the pharmacology, clinical activity, and adverse effects of an adriamycin analogue. J Clin Oncol. 1986 Mar;4(3):425-39. [2]. Ozkan, A., et al. Epirubicin HCl toxicity in human-liver derived hepatoma G2 cells. Pol J Pharmacol, 2004. 56(4): p. 435-44. [3]. Bonadonna, G., et al. Drugs ten years later: epirubicin. Ann Oncol, 1993. 4(5): p. 359-69. [4]. Asanuma, F., et al. Antitumor activity of paclitaxel and epirubicin in human breast carcinoma, R-27. Folia Microbiol (Praha), 1998. 43(5): p. 473-4.

Density	1.61g/cm3
Boiling Point	810.3ºC at 760 mmHg
Melting Point	185ºC dec
Molecular Formula	C₂₇H₃₀ClNO₁₁
Molecular Weight	579.980
Flash Point	443.8ºC
Exact Mass	579.150757
PSA	206.07000
LogP	1.50360
Index of Refraction	1.709

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9295750

CHEMICAL NAME :: 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyran osyl)oxy)- 7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacety l)-1-methoxy-, hydrochloride, (8S-cis)-

CAS REGISTRY NUMBER :: 56390-09-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C27-H29-N-O11.Cl-H

MOLECULAR WEIGHT :: 580.03

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1622 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Gastrointestinal - changes in structure or function of salivary glands Immunological Including Allergic - uncharacterized

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,629,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,740,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2250 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,200,1990

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H302-H340-H350-H360
Precautionary Statements	P201-P280-P301 + P312 + P330-P308 + P313
Hazard Codes	Xn
Risk Phrases	22-63-62-46-40
Safety Phrases	36/37/38-45-46
RIDADR	NONH for all modes of transport
RTECS	QI9295750
HS Code	2932999099

HS Code	2932999099
Summary	2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Fourier transform infrared spectroscopy imaging of live epithelial cancer cells under non-aqueous media.

J. Clin. Pathol. 66(4) , 312-8, (2013)

Fourier transform infrared (FT-IR) imaging is increasingly being applied to biomedical specimens, but strong IR absorption by water complicates live cell imaging. This study investigates the viability...

Intraabdominal follicular dendritic cell sarcoma: a report of three cases and review of the literature.

Tumori 99(2) , e65-9, (2013)

Follicular dendritic cell sarcoma (FDCS) is a rare neoplasm that originates from follicular dendritic cells in lymphoid follicles. FDCS has been increasingly reported in recent years. However, data on...

Treatment outcome in children and adolescents with relapsed Hodgkin lymphoma--results of the UK HD3 relapse treatment strategy.

Br. J. Haematol. 165(4) , 534-44, (2014)

The purpose of this national retrospective study was to evaluate the outcome in children with relapsed or primary refractory Hodgkin lymphoma [HL] after a primary chemotherapy alone treatment strategy...

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-, (8S,10S)-, hydrochloride

(1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside 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-(hydroxyacetyl)-1-methoxy-, hydrochloride

Pidorubicin 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-, (8S,10S)-, hydrochloride (1:1)

Ellence

(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride

Epirubicin hydrochloride

(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride (1:1)

EINECS 260-145-2

(8S,10S)-10-{[(2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracen-5,12-dionhydrochlorid

EPIRUBICIN HCl

(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

Epirubicin (hydrochloride)