- Overview
- Properties
- Genetics
- Related Genes
- Related Drugs
- Related Diseases
- Datasets
- Downloads/LinkOuts
Overview
| Trade Names: | 4'-Epiadriamycin; 4'-Epidoxorubicin; Ellence; Epi-Dx; Epiadriamycin; Epidoxorubicin; Epirubicina [INN-Spanish]; Epirubicina [Spanish]; Epirubicine [French]; Epirubicine [INN-French]; Epirubicinum [INN-Latin]; Epirubicinum [Latin]; IMI 28; Pharmorubicin Pfs; Pidorubicina [INN-Spanish]; Pidorubicine [INN-French]; Pidorubicinum [INN-Latin]; Ridorubicin |
|---|---|
| PharmGKB Accession Id: | PA449476 |
Description
An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. PubChem (source: Drug Bank)
Indication
For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer (source: Drug Bank)
ATC Therapeutic Category
- L01DB:Anthracyclines and related substances
Pharmacology, Interactions, and Contraindications
Mechanism Of Action
Epirubicin has antimitotic and cytotoxic activity. It inhibits nucleic acid (DNA and RNA) and protein synthesis through a number of proposed mechanisms of action: Epirubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It also interferes with DNA replication and transcription by inhibiting DNA helicase activity. (source: Drug Bank)
Pharmacology
Epirubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Epirubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Epirubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific. (source: Drug Bank)
Food Interactions
Liberal fluid intake to increase urine output and help the excretion of uric acid. (source: Drug Bank)
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic (source: Drug Bank)
Protein Binding
77% (source: Drug Bank)
Absorption
100% (source: Drug Bank)
Toxicity
bone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding (source: Drug Bank)
Isomeric SMILES Code:
C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N)O (source: Drug Bank)
Curated Annotations (
)
-
rs1045642
at chr7:86976581
in
ABCB1
In Slovak (White) breast cancer patients (n=221) receiving anthracycline-based chemotherapy, the CC genotype of ABCB1:3435C>T was associated with longer time to progression.- Variant Name:
- ABCB1:3435C>T; MDR1 C3435T
- Related Drugs:
- doxorubicin, epirubicin
- Related Diseases:
- Breast Neoplasms
- Evidence:
-
PMID:19752884
-
rs1800566
at chr16:68302646
in
NQO1
This homozygous variant predicts poor survival among two independent series of women with breast cancer. This effect is particularly evident after anthracycline-based adjuvant chemotherapy with epirubicin and in p53-aberrant tumors.- Variant Name:
- NQO1:c.558C>T; NQO1(*)2
- Related Drugs:
- epirubicin
- Related Diseases:
- Breast Neoplasms
- Evidence:
-
PMID:18511948
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
|
ABCB1 |
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Publications, Variants |
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ABCC1 |
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Publications |
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CBR3 |
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Publications |
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ERBB2 |
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Publications |
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NQO1 |
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Publications, Variants |
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SOD2 |
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Publications |
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TOP2A |
|
Publications |
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UGT2B7 |
|
Publications |
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
| Gene | Description | |
|---|---|---|
| CHD1 |
|
(source: Drug Bank) |
| TOP2A |
|
(source: Drug Bank) |
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| Drug | Description | |
|---|---|---|
| cimetidine |
|
Cimetidine can increase epirubicin levels (source: Drug Bank) |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
|---|---|---|---|
|
|
Breast Neoplasms |
|
Publications, Variants |
|
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Cardiomyopathies |
|
Publications |
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Drug Resistance |
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Publications |
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Drug Toxicity |
|
Publications |
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Esophogeal Neoplasms |
|
Publications |
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Heart Failure |
|
Publications |
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Mesothelioma |
|
Publications |
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Neoplasms |
|
Publications |
|
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Stomach Neoplasms |
|
Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Curated Phenotype Datasets
These datasets are sorted alphabetically by title.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
Downloads
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LinkOuts
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.