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56390-09-1

56390-09-1 structure
56390-09-1 structure
  • Name: Epirubicin hydrochloride
  • Chemical Name: Epirubicin hydrochloride
  • CAS Number: 56390-09-1
  • Molecular Formula: C27H30ClNO11
  • Molecular Weight: 579.980
  • Catalog: API Antineoplastic agents Antibiotic antineoplastic agents
  • Create Date: 2018-05-28 08:00:00
  • Modify Date: 2024-01-02 15:11:07
  • Epirubicin (hydrochloride) is a semisynthetic L-arabino derivative of doxorubicin, and an antineoplastic agent by inhibiting Topoisomerase.
Name Epirubicin hydrochloride
Synonyms 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)
Description Epirubicin (hydrochloride) is a semisynthetic L-arabino derivative of doxorubicin, and an antineoplastic agent by inhibiting Topoisomerase.
Related Catalog
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
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%

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