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Epirubicin

Epirubicin structure

CAS No:
56420-45-2
Formula:
C27H29NO11
Chemical Name:
Epirubicin
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-(2-hydroxyacetyl)-1-methoxy-,(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-,(8S-cis)-;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)-;(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;NSC 256942;4′-epi-Doxorubicin;4′-Epidoxorubicin;4′-Epiadriamycin;4′-epi-Adriamycin;Epirubicin;Epiadriamycin;Epidoxorubicin;WP 697;Farmarubicin;Farmarubicine;Pharmarubicin;4′-Epi-DX;IMI 28;Pidorubicin;Epirarubicin;Ebeve;Epirubicin Ebewe;57918-25-9
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

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

Epirubicin Basic Attributes

Molecular Weight：

543.52

Exact Mass：

543.52

Characteristics

PSA：

206

XLogP3：

-0.5

Density：

1.6±0.1 g/cm3

Melting Point：

344.53 °C

Boiling Point：

810.3±65.0 °C at 760 mmHg

Flash Point：

443.8±34.3 °C

Refractive Index：

1.710

Water Solubility：

1.18e+00 g/L

Storage Conditions：

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: -20 deg C. /Epirubicin hydrochloride/

Vapor Pressure：

2.50X10-23 mm Hg at 25 deg C (est)

Toxicity：

LD50 intravenous in dog: 2mg/kg

Safety Information

Stability/Shelf Life：

The stability of epirubicin in sodium chloride 0.9% injection, the degradation kinetics of an epirubicin 1 mg/ml solution and the stability of epirubicin 2 mg/ml in polypropylene syringes stored under hospital conditions were studied at various temperature. The degradation of epirubicin in sodium chloride 0.9% solutions followed first order kinetics. The shelf life was defined as the time by which the epirubicin concentration had decreased by 10% from the initial concentration. Epirubicin was st

Epirubicin Use and Manufacturing

Methods of Manufacturing

Compound (I) is N-acylated with trifluoroacetic anhydride to protect the amino group to obtain compound (II). It is oxidized to ketone (III), and then reduced to alcohol (IV). The ether bond is removed under the action of acid, and then esterified with trifluoroacetic anhydride to compound (VI), and then selectively chlorinated to obtain the desired side chain (VII). Compound (VIII) is reacted with dimethylacetal to form ketal (IX), and then reacted with the side chain (VII) prepared above, and the obtained compound (X) is hydrolyzed to obtain epirubicin.

Uses

For anti-tumor

Computed Properties

Molecular Weight:543.5
XLogP3:1.3
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:5
Exact Mass:543.17406074
Monoisotopic Mass:543.17406074
Topological Polar Surface Area:206
Heavy Atom Count:39
Complexity:977
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is the main isomer of doxorubicin, which is the trans configuration of the C4 hydroxyl group in the amino sugar part of doxorubicin. It can be directly embedded in DNA, form a complex with the double helix structure of DNA, block the formation of RNA dependent on DNA, and has the kinetic energy to form superoxide radicals. The site of action of this product is on the C4 hydroxyl group of the amino sugar part (its excretion amount can reach 1/3 of the total excretion amount). This was only found after using this drug, but not when using daunorubicin and doxorubicin. This may be the main reason why epirubicin is cleared faster in the body and its toxicity is lower than that of doxorubicin at the same dose.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Epirubicin Hydrochloride for Injection
Ingredients	Epirubicin.
Indication	1 Epirubicin can be used in combination with other anti-tumor drugs, but the dosage of epirubicin should be reduced. When used in combination, they should not be used in the same syringe. 2 Epirubicin should not be mixed with heparin for injection, because the two are chemically incompatible and precipitation reactions will occur at a certain concentration.
Specifications	10 mg

Epirubicin Hydrochloride Injection
Ingredients	The main ingredient is epirubicin.
Indication	1 Epirubicin can be used in combination with other anti-tumor drugs, but the dosage of epirubicin should be reduced. When used in combination, they should not be used in the same syringe. 2 Epirubicin should not be mixed with heparin for injection, because the two are chemically incompatible and precipitation reactions will occur at a certain concentration.

Epirubicin Hydrochloride for Injection
Ingredients	Epirubicin.
Indication	1 Epirubicin can be used in combination with other anti-tumor drugs, but the dosage of epirubicin should be reduced. When used in combination, they should not be used in the same syringe. 2 Epirubicin should not be mixed with heparin for injection, because the two are chemically incompatible and precipitation reactions will occur at a certain concentration.
Specifications	10 mg
Manufacturer	Pfizer Pharmaceutical Wuxi Co., Ltd.

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