Identification

Name
Epirubicin
Accession Number
DB00445  (APRD00361)
Type
Small Molecule
Groups
Approved
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]

Structure
Thumb
Synonyms
  • 4'-Epiadriamycin
  • Epiadriamycin
  • Epirubicin
  • Epirubicina
  • Epirubicine
  • Epirubicinum
  • Pidorubicina
  • Pidorubicine
  • Pidorubicinum
External IDs
NSC-256942
Product Ingredients
IngredientUNIICASInChI Key
Epirubicin hydrochloride22966TX7J556390-09-1MWWSFMDVAYGXBV-FGBSZODSSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EllenceInjection, solution2 mg/mLIntravenousPharmacia & Upjohn Inc1999-09-15Not applicableUs
EllenceInjection, solution2 mg/mLIntravenousPharmacia & Upjohn Inc1999-09-15Not applicableUs
Epirubicin for InjectionSolution2 mgIntravenousTeva2009-09-14Not applicableCanada
Epirubicin Hydrochloride for InjectionPowder, for solution50 mgIntravenousHospira, Inc.2008-04-07Not applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousUman PharmaNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2.0 mgIntravenousFresenius Kabi2009-03-24Not applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousOmega Laboratories LtdNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousAccord Healthcare Limited2008-11-282012-10-03Canada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousPartners Health Care, Inc.Not applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Epirubicin HydrochlorideInjection, solution50 mg/25mLIntravenousTeva Parenteral Medicines, Inc.2007-08-092017-11-30Us
Epirubicin HydrochlorideInjection2 mg/mLIntravenousAreva Pharmaceuticals,Inc.2012-07-16Not applicableUs
Epirubicin HydrochlorideInjection200 mg/100mLIntravenousAmneal Agila, Llc2013-07-312018-02-20Us
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousSandoz2009-12-22Not applicableUs
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousGreenstone, Llc1999-09-15Not applicableUs
Epirubicin HydrochlorideInjection2 mg/mLIntravenousWest Ward Pharmaceutical2007-08-07Not applicableUs
Epirubicin HydrochlorideInjection, solution200 mg/100mLIntravenousTeva Parenteral Medicines, Inc.2007-08-092017-03-31Us
Epirubicin HydrochlorideInjection200 mg/100mLIntravenousMylan Institutional2013-07-312018-01-28Us
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousHospira Worldwide, Inc.2007-04-192017-10-26Us
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousFresenius Kabi2017-07-31Not applicableUs
International/Other Brands
Epirubicin Ebewe / Pharmorubicin
Categories
UNII
3Z8479ZZ5X
CAS number
56420-45-2
Weight
Average: 543.5193
Monoisotopic: 543.174060775
Chemical Formula
C27H29NO11
InChI Key
AOJJSUZBOXZQNB-VTZDEGQISA-N
InChI
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1
IUPAC Name
(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
SMILES
COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O

Pharmacology

Indication

For use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer.

Associated Conditions
Pharmacodynamics

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.

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.

TargetActionsOrganism
AChromodomain-helicase-DNA-binding protein 1
antagonist
Human
UDNA topoisomerase 2-alpha
inhibitor
Human
UDNA
intercalation
Human
Absorption

100%

Volume of distribution
  • 21 ± 2 L/kg [60 mg/m2 Dose]
  • 27 ± 11 L/kg [75 mg/m2 Dose]
  • 23 ± 7 L/kg [120 mg/m2 Dose]
  • 21 ± 7 L/kg [150 mg/m2 Dose]
Protein binding

77%

Metabolism

Extensively and rapidly metabolized in the liver. Epirubicin is also metabolized by other organs and cells, including red blood cells. The four main metabolic routes are: (1) reduction of the C-13 keto-group with the formation of the 13(S)-dihydro derivative, epirubicinol; (2) conjugation of both the unchanged drug and epirubicinol with glucuronic acid; (3) loss of the amino sugar moiety through a hydrolytic process with the formation of the doxorubicin and doxorubicinol aglycones; and (4) loss of the amino sugar moiety through a redox process with the formation of the 7-deoxy-doxorubicin aglycone and 7-deoxy-doxorubicinol aglycone. Epirubicinol exhibits in vitro cytoxic activity (~10% that of epirubicin), but it is unlikely to reach sufficient concentrations in vivo to produce cytotoxic effects.

Route of elimination

Epirubicin and its major metabolites are eliminated through biliary excretion and, to a lesser extent, by urinary excretion.

Half life

Half-lives for the alpha, beta, and gamma phases of about 3 minutes, 2.5 hours and 33 hours, respectively

Clearance
  • 65 +/- 8 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 60 mg/m2]
  • 83 +/- 14 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 75 mg/m2]
  • 65 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 120 mg/m2]
  • 69 +/- 13 L/hour [Patients1 with Solid Tumors Receiving Intravenous Epirubicin 150 mg/m2]
Toxicity

bone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Epirubicin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Epirubicin.Experimental
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Epirubicin.Approved, Investigational, Withdrawn
Anthrax immune globulin humanThe risk or severity of adverse effects can be increased when Epirubicin is combined with Anthrax immune globulin human.Approved
Bacillus calmette-guerin substrain connaught live antigenThe risk or severity of adverse effects can be increased when Epirubicin is combined with Bacillus calmette-guerin substrain connaught live antigen.Approved, Investigational
Bacillus calmette-guerin substrain tice live antigenThe risk or severity of adverse effects can be increased when Epirubicin is combined with Bacillus calmette-guerin substrain tice live antigen.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Epirubicin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Epirubicin.Approved
CimetidineThe serum concentration of Epirubicin can be increased when it is combined with Cimetidine.Approved, Investigational
Clostridium tetani toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Epirubicin is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated).Approved
ClozapineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Clozapine.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Epirubicin is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated).Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Epirubicin.Experimental
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Epirubicin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Epirubicin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Epirubicin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Epirubicin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Epirubicin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Epirubicin.Approved, Investigational
FingolimodEpirubicin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Epirubicin is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Epirubicin is combined with GI-5005.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Epirubicin.Experimental
Hepatitis A VaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Hepatitis A Vaccine.Approved
Hepatitis B Vaccine (Recombinant)The risk or severity of adverse effects can be increased when Epirubicin is combined with Hepatitis B Vaccine (Recombinant).Approved, Withdrawn
Human rabies virus immune globulinThe risk or severity of adverse effects can be increased when Epirubicin is combined with Human rabies virus immune globulin.Approved
INGN 201The risk or severity of adverse effects can be increased when Epirubicin is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Epirubicin is combined with INGN 225.Investigational
Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Epirubicin is combined with Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated).Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Epirubicin.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Epirubicin is combined with Leflunomide.Approved, Investigational
LipegfilgrastimEpirubicin may increase the myelosuppressive activities of Lipegfilgrastim.Approved, Investigational
MetamizoleThe risk or severity of myelosuppression can be increased when Metamizole is combined with Epirubicin.Approved, Investigational, Withdrawn
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Epirubicin.Experimental
NatalizumabThe risk or severity of adverse effects can be increased when Epirubicin is combined with Natalizumab.Approved, Investigational
OcrelizumabOcrelizumab may increase the immunosuppressive activities of Epirubicin.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Epirubicin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Epirubicin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Epirubicin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Epirubicin.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Epirubicin.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Epirubicin.Experimental
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Epirubicin is combined with Rabies virus inactivated antigen, A.Approved, Investigational
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Epirubicin.Approved, Investigational
RindopepimutThe risk or severity of adverse effects can be increased when Epirubicin is combined with Rindopepimut.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Epirubicin.Approved
Rotavirus VaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Rotavirus Vaccine.Approved
Rubella virus vaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Rubella virus vaccine.Approved, Investigational
Salmonella typhi ty2 vi polysaccharide antigenThe risk or severity of adverse effects can be increased when Epirubicin is combined with Salmonella typhi ty2 vi polysaccharide antigen.Approved
Salmonella typhi ty21a live antigenThe risk or severity of adverse effects can be increased when Epirubicin is combined with Salmonella typhi ty21a live antigen.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Epirubicin.Approved, Investigational
SRP 299The risk or severity of adverse effects can be increased when Epirubicin is combined with SRP 299.Investigational
TacrolimusTacrolimus may increase the immunosuppressive activities of Epirubicin.Approved, Investigational
TecemotideThe risk or severity of adverse effects can be increased when Epirubicin is combined with Tecemotide.Investigational
TG4010The risk or severity of adverse effects can be increased when Epirubicin is combined with TG4010.Investigational
TofacitinibEpirubicin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
Typhoid VaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Typhoid Vaccine.Approved
Varicella Zoster Vaccine (Live/Attenuated)The risk or severity of adverse effects can be increased when Epirubicin is combined with Varicella Zoster Vaccine (Live/Attenuated).Approved
Yellow Fever VaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Yellow Fever Vaccine.Approved, Investigational
Food Interactions
  • Liberal fluid intake to increase urine output and help the excretion of uric acid.

References

Synthesis Reference

Marcel van der Rijst, Johan Wilhelm Scheeren, Dick de Vos, "Process for preparing epirubicin or acid addition salts thereof from daunorubicin." U.S. Patent US5874550, issued September, 1996.

US5874550
General References
Not Available
External Links
Human Metabolome Database
HMDB0014588
KEGG Compound
C11230
PubChem Compound
41867
PubChem Substance
46507282
ChemSpider
38201
BindingDB
43839
ChEBI
47898
ChEMBL
CHEMBL417
Therapeutic Targets Database
DAP000193
PharmGKB
PA449476
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Epirubicin
ATC Codes
L01DB03 — Epirubicin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (92.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedPreventionGastro-esophageal Junction Cancer / Malignant Neoplasm of Stomach1
1Active Not RecruitingTreatmentEsophageal Cancers / Malignant Neoplasm of Cardio-esophageal Junction of Stomach1
1Active Not RecruitingTreatmentEstrogen Receptor Negative / HER2/Neu Negative / Male Breast Carcinoma / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v7 / Triple-Negative Breast Carcinoma1
1Active Not RecruitingTreatmentSarcomas1
1CompletedTreatmentCancer, Breast3
1CompletedTreatmentCancer, Breast / Neutropenias1
1CompletedTreatmentExtrahepatic Bile Duct Cancer / Gallbladder Cancer / Liver Cancer / Malignant Neoplasm of Stomach / Unspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentMetastatic Breast Cancer (MBC)2
1CompletedTreatmentNeoplams, Advanced / Neoplasms, Advanced1
1CompletedTreatmentNeoplasms, Breast1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific2
1RecruitingTreatmentCancer, Breast1
1RecruitingTreatmentInflammatory carcinoma of the breast1
1TerminatedTreatmentProstate Cancer1
1, 2CompletedTreatmentCancer, Breast2
1, 2CompletedTreatmentCancer, Breast / Neutropenias1
1, 2CompletedTreatmentEsophageal Cancers / Esophagogastric Junction Adenocarcinoma / Malignant Neoplasm of Stomach1
1, 2CompletedTreatmentEsophageal Cancers / Extrahepatic Bile Duct Cancer / Head and Neck Carcinoma / Liver Cancer / Malignant Neoplasm of Stomach / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2CompletedTreatmentLiver Cancer1
1, 2RecruitingTreatmentAdvanced Hepatocellular Carcinoma / Recurrence Hepatocellular Carcinoma1
1, 2RecruitingTreatmentCancer, Breast / Luminal B / Triple Negative Breast Cancer (TNBC)1
1, 2RecruitingTreatmentT Cell Non-Hodgkin's Lymphoma1
1, 2TerminatedTreatmentAdenocarcinoma Of Esophagus / Gastric Adenocarcinoma1
1, 2TerminatedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach / Tumors1
1, 2TerminatedTreatmentNeoplasms1
2Active Not RecruitingTreatmentCLDN18.2-positive Adenocarcinoma of Esophagus / CLDN18.2-positive Adenocarcinoma of the Gastroesophageal Junction / CLDN18.2-positive Gastric Adenocarcinoma1
2Active Not RecruitingTreatmentCancer, Breast8
2Active Not RecruitingTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
2Active Not RecruitingTreatmentHer2-Positive Breast Cancer1
2Active Not RecruitingTreatmentMalignant Neoplasm of Female Breast1
2Active Not RecruitingTreatmentNeoadjuvant Operable Breast Cancer1
2Active Not RecruitingTreatmentNeoplasms, Breast1
2Active Not RecruitingTreatmentPleomorphic Rhabdomyosarcoma / Stage IIB Adult Soft Tissue Sarcoma / Stage IIB Adult Soft Tissue Sarcoma AJCC v7 / Stage III Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma AJCC v7 / Stage IV Adult Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma AJCC v71
2CompletedPreventionGrade 3/4 Neutropenia / Neutropenia, Febrile1
2CompletedPreventionHepatocellular,Carcinoma1
2CompletedTreatmentAdenocarcinoma Of Esophagus1
2CompletedTreatmentAdvanced Gastric Cancer1
2CompletedTreatmentCancer of the Ovary / Sarcomas / Small Intestine Cancer1
2CompletedTreatmentCancer, Breast12
2CompletedTreatmentCancer, Breast / Locally Advanced / Stage IIB Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentEsophageal Cancers1
2CompletedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
2CompletedTreatmentGastro Oesophageal Cancer1
2CompletedTreatmentGastroesophageal Junction Neoplasms / Stomach Neoplasms1
2CompletedTreatmentIndividualized Chemotherapy1
2CompletedTreatmentLeukemias / Malignant Lymphomas1
2CompletedTreatmentLiver Cancer1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL) / POOR PROGNOSIS1
2CompletedTreatmentMalignant Neoplasm of Pancreas2
2CompletedTreatmentMalignant Neoplasm of Stomach2
2CompletedTreatmentMelanoma (Skin)1
2CompletedTreatmentMesothelioma, Malignant1
2CompletedTreatmentNeoplasms, Breast3
2CompletedTreatmentOesophageal Carcinoma1
2CompletedTreatmentPathological Response Rate1
2CompletedTreatmentPrimary Breast Cancer1
2CompletedTreatmentStomach Neoplasms1
2CompletedTreatmentTesticular Neoplasms1
2CompletedTreatmentUnilateral HER2 Positive Breast Cancer1
2Not Yet RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Childhood Cancers / Down Syndrome (DS)1
2Not Yet RecruitingTreatmentInflammatory carcinoma of the breast1
2Not Yet RecruitingTreatmentMalignant Neoplasm of Stomach / Stomach Neoplasms1
2Not Yet RecruitingTreatmentStage II Breast Cancer / Stage III Breast Cancer1
2RecruitingBasic ScienceCancer, Breast1
2RecruitingTreatmentAdenocarcinomas of the Esophagogastric Junction1
2RecruitingTreatmentBCT Rate / PCR Rate / Safety1
2RecruitingTreatmentCancer, Breast5
2RecruitingTreatmentCancer, Breast / Neoadjuvant Chemotherapy1
2RecruitingTreatmentEstrogen Receptor-negative Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-negative Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Triple-Negative Breast Cancer (TNBC)1
2RecruitingTreatmentHER2 Positive Breast Cancers / Inflammatory carcinoma of the breast / Invasive Ductal Breast Carcinoma / Malignant Neoplasm of Female Breast / Mucinous Breast Cancer Stage II / Tubular Breast Cancer Stage II / Tubular Breast Cancer Stage III1
2RecruitingTreatmentMalignant Neoplasm of Breast1
2RecruitingTreatmentNeoplasms, Breast4
2RecruitingTreatmentNeoplasms, Esophageal / Stomach Neoplasms1
2TerminatedDiagnosticCancer, Breast1
2TerminatedTreatmentAdenocarcinomas of the Gastroesophageal Junction / Malignant Neoplasm of Stomach1
2TerminatedTreatmentCancer of the Ovary / Childhood Germ Cell Tumor / Extragonadal Germ Cell Tumor / Testicular germ cell tumour1
2TerminatedTreatmentCancer, Breast7
2TerminatedTreatmentKRAS Wild Type / Resectable Type II Gastric Adenocarcinoma1
2TerminatedTreatmentLower Oesophagus Cancer / Oesophageal Junction Cancer / Stomach Neoplasms1
2TerminatedTreatmentMalignant Neoplasm of Pancreas1
2TerminatedTreatmentNeoplasms, Breast1
2Unknown StatusTreatmentCancer, Breast2
2Unknown StatusTreatmentHER-2 Positive Breast Cancer1
2Unknown StatusTreatmentMalignant Lymphomas1
2Unknown StatusTreatmentMalignant Lymphomas / Small Intestine Cancer1
2Unknown StatusTreatmentMalignant Neoplasm of Stomach1
2Unknown StatusTreatmentProstate Cancer1
2Unknown StatusTreatmentTriple Negative Breast Cancer (TNBC)1
2WithdrawnTreatmentNeoplasms, Breast1
2, 3Active Not RecruitingTreatmentMalignant Neoplasm of Stomach1
2, 3CompletedTreatmentCancer, Breast1
2, 3CompletedTreatmentMalignant Neoplasm of Pancreas1
2, 3Not Yet RecruitingTreatmentCancer treatment / Cancer, Breast / Endocrine Breast Diseases1
2, 3Not Yet RecruitingTreatmentCancer, Breast / Neoadjuvant Chemotherapy / Pathological Complete Response1
2, 3Not Yet RecruitingTreatmentStage III Breast Cancer1
2, 3RecruitingTreatmentCancer, Breast1
2, 3RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
2, 3RecruitingTreatmentMalignant Neoplasm of Stomach1
2, 3RecruitingTreatmentOesophagogastric Cancer1
2, 3Unknown StatusTreatmentHepatocellular,Carcinoma1
3Active Not RecruitingNot AvailableCancer, Breast1
3Active Not RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
3Active Not RecruitingTreatmentCancer, Breast8
3Active Not RecruitingTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
3Active Not RecruitingTreatmentHER2/Neu Positive / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer1
3Active Not RecruitingTreatmentHer2 Non-overexpressing / Primary Breast Cancer1
3Active Not RecruitingTreatmentMalignant Lymphomas1
3Active Not RecruitingTreatmentMalignant Neoplasm of Stomach1
3CompletedPreventionCancer, Breast1
3CompletedSupportive CareCancer, Breast1
3CompletedTreatmentAdenocarcinomas1
3CompletedTreatmentCancer of the Ovary / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer1
3CompletedTreatmentCancer, Breast32
3CompletedTreatmentCancer, Breast / Chemotherapy, Adjuvant1
3CompletedTreatmentChildhood Malignant Fibrous Histiocytoma of Bone / Sarcomas1
3CompletedTreatmentEarly Stage Breast Cancer1
3CompletedTreatmentElderly Patients (>65 Years) / Lymphoma, Large B-Cell, Diffuse (DLBCL)1
3CompletedTreatmentEndometrial Cancers1
3CompletedTreatmentHER2 Positive Breast Cancers / Inflammatory carcinoma of the breast / Invasive Ductal Breast Carcinoma / Malignant Neoplasm of Female Breast / Mucinous Breast Cancer Stage II / Tubular Breast Cancer Stage II / Tubular Breast Cancer Stage III1
3CompletedTreatmentInflammatory carcinoma of the breast1
3CompletedTreatmentMalignant Neoplasm of Female Breast1
3CompletedTreatmentMalignant Neoplasm of Stomach2
3CompletedTreatmentMetastatic Breast Cancer (MBC)1
3CompletedTreatmentNeoplasms, Breast1
3CompletedTreatmentSmall Cell Lung Carcinoma, Extensive Disease1
3Enrolling by InvitationTreatmentNasopharyngeal Carcinoma1
3RecruitingTreatmentAdenocarcinoma of the Oesophago-gastric Junction / Adenocarcinoma of the Oesophagus / Junctional Tumours / Malignant Neoplasm of Esophagus / Oesophageal Tumours1
3RecruitingTreatmentBreast Cancer Model / Cancer, Breast / Effects of Chemotherapy1
3RecruitingTreatmentCancer, Breast2
3RecruitingTreatmentCancer, Breast / Her2-Positive Breast Cancer / Neoplasms, Breast / Stage II Breast Cancer / Stage IIIA Breast Cancer1
3RecruitingTreatmentHER2 Positive Breast Cancers1
3RecruitingTreatmentHepatocellular,Carcinoma2
3RecruitingTreatmentHepatocellular,Carcinoma / Portal Vein Tumor Thrombus1
3RecruitingTreatmentInflammatory carcinoma of the breast / Invasive Ductal Breast Carcinoma / Mucinous Breast Cancer / Tubular Breast Carcinoma1
3RecruitingTreatmentInvasive Duct Carcinoma of Breast / Mucinous Breast Cancer / Tubular Breast Carcinoma1
3RecruitingTreatmentLocally Advanced Unresectable Gastric Cancer / Metastatic Gastric Cancers1
3RecruitingTreatmentMalignant Neoplasm of Stomach1
3RecruitingTreatmentMalignant Neoplasm of Stomach / Stomach Neoplasms1
3RecruitingTreatmentTriple Negative Breast Neoplasms1
3TerminatedTreatmentCancer, Breast3
3TerminatedTreatmentMalignant Neoplasm of Stomach1
3TerminatedTreatmentOesophago-gastric Cancer1
3Unknown StatusDiagnosticCancer, Breast1
3Unknown StatusTreatmentBladder Cancers1
3Unknown StatusTreatmentCancer, Breast10
3Unknown StatusTreatmentCancer, Breast / Cardiac Toxicity / Perioperative/Postoperative Complications1
3Unknown StatusTreatmentCancer treatment / Cancer, Breast1
3Unknown StatusTreatmentCarcinoma of Unknown Primary1
3Unknown StatusTreatmentEsophageal Cancers1
3Unknown StatusTreatmentLung Cancers2
3WithdrawnTreatmentHepatocellular,Carcinoma1
4CompletedPreventionCarcinoma of Urinary Bladder, Superficial1
4CompletedTreatmentCancer, Breast1
4Not Yet RecruitingTreatmentHepatocellular,Carcinoma / Neoplastic Cells, Circulating1
4RecruitingTreatmentCancer, Breast2
4RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
4RecruitingTreatmentNeoplasms, Breast1
4Unknown StatusTreatmentCancer, Breast1
4Unknown StatusTreatmentMetastatic Breast Cancer (MBC)1
Not AvailableCompletedDiagnosticCancer, Breast1
Not AvailableCompletedTreatmentAdenocarcinoma of the Breast / Cancer, Breast1
Not AvailableCompletedTreatmentCancer, Breast / Stage I Breast Carcinoma / Stage II Breast Cancer / Stage IIIA Breast Cancer1
Not AvailableNot Yet RecruitingTreatmentUrinary Bladder Neoplasms1
Not AvailableRecruitingTreatmentBreast Cancer Nos Premenopausal1
Not AvailableRecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
Not AvailableTerminatedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
Not AvailableUnknown StatusTreatmentCancer, Breast2
Not AvailableWithdrawnTreatmentCancer, Breast1

Pharmacoeconomics

Manufacturers
  • Pfizer inc
  • Actavis totowa llc
  • Akorn inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Bioniche pharma usa llc
  • Ebewe pharma ges mbh nfg kg
  • Fresenius kabi oncology plc
  • Hospira inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • X gen pharmaceuticals inc
Packagers
  • APP Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Cipla Ltd.
  • Ebewe Pharma
  • Ethex Corp.
  • Fresenius Kabi AB
  • Generamedix Inc.
  • Greenstone LLC
  • Hospira Inc.
  • Intas Pharmaceuticals Ltd.
  • Otn Generics Inc.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Sagent Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
InjectionIntravenous2 mg/mL
InjectionIntravenous200 mg/100mL
InjectionIntravenous50 mg/25mL
Injection, solutionIntravenous2 mg/mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous50 mg/25mL
Powder, for solutionIntravenous50 mg
SolutionIntravenous2 mg
SolutionIntravenous2.0 mg
Powder, for solutionIntravenous10 mg
Prices
Unit descriptionCostUnit
Epirubicin hcl 200 mg vial2845.85USD vial
Epirubicin hcl 50 mg vial69.54USD vial
Ellence 2 mg/ml vial5.38USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)344.53 °CNot Available
water solubility0.093 mg/mlNot Available
logP-0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.18 mg/mLALOGPS
logP1.41ALOGPS
logP0.92ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity134.59 m3·mol-1ChemAxon
Polarizability53.88 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8092
Blood Brain Barrier-0.9951
Caco-2 permeable-0.799
P-glycoprotein substrateSubstrate0.7861
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.8042
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5888
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9209
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8911
Ames testAMES toxic0.9198
CarcinogenicityNon-carcinogens0.9534
BiodegradationNot ready biodegradable0.9672
Rat acute toxicity2.6644 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9752
hERG inhibition (predictor II)Non-inhibitor0.7195
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0309010000-24e2012ac5fb139c1f97

Taxonomy

Description
This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Anthracyclines
Sub Class
Not Available
Direct Parent
Anthracyclines
Alternative Parents
Tetracenequinones / Aminoglycosides / Anthraquinones / Hexoses / O-glycosyl compounds / Tetralins / Anisoles / Aryl ketones / Alkyl aryl ethers / Oxanes
show 13 more
Substituents
Anthracycline / Anthracyclinone-skeleton / Aminoglycoside core / Tetracenequinone / 9,10-anthraquinone / 1,4-anthraquinone / Anthracene / Hexose monosaccharide / Glycosyl compound / O-glycosyl compound
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinone, monosaccharide derivative, anthracycline antibiotic, aminoglycoside, deoxy hexoside, anthracycline (CHEBI:47898)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Methylated histone binding
Specific Function
ATP-dependent chromatin-remodeling factor which functions as substrate recognition component of the transcription regulatory histone acetylation (HAT) complex SAGA. Regulates polymerase II transcri...
Gene Name
CHD1
Uniprot ID
O14646
Uniprot Name
Chromodomain-helicase-DNA-binding protein 1
Molecular Weight
196685.865 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Petit T, Wilt M, Velten M, Millon R, Rodier JF, Borel C, Mors R, Haegele P, Eber M, Ghnassia JP: Comparative value of tumour grade, hormonal receptors, Ki-67, HER-2 and topoisomerase II alpha status as predictive markers in breast cancer patients treated with neoadjuvant anthracycline-based chemotherapy. Eur J Cancer. 2004 Jan;40(2):205-11. [PubMed:14728934]
  2. Knoop AS, Knudsen H, Balslev E, Rasmussen BB, Overgaard J, Nielsen KV, Schonau A, Gunnarsdottir K, Olsen KE, Mouridsen H, Ejlertsen B: retrospective analysis of topoisomerase IIa amplifications and deletions as predictive markers in primary breast cancer patients randomly assigned to cyclophosphamide, methotrexate, and fluorouracil or cyclophosphamide, epirubicin, and fluorouracil: Danish Breast Cancer Cooperative Group. J Clin Oncol. 2005 Oct 20;23(30):7483-90. [PubMed:16234514]
  3. Liang CH, Shiu LY, Chang LC, Sheu HM, Kuo KW: Solamargine upregulation of Fas, downregulation of HER2, and enhancement of cytotoxicity using epirubicin in NSCLC cells. Mol Nutr Food Res. 2007 Aug;51(8):999-1005. [PubMed:17639997]
3. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
Actions
Intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Ganzina F: 4'-epi-doxorubicin, a new analogue of doxorubicin: a preliminary overview of preclinical and clinical data. Cancer Treat Rev. 1983 Mar;10(1):1-22. [PubMed:6342772]
  2. Williams LD, Frederick CA, Ughetto G, Rich A: Ternary interactions of spermine with DNA: 4'-epiadriamycin and other DNA: anthracycline complexes. Nucleic Acids Res. 1990 Sep 25;18(18):5533-41. [PubMed:2216725]
  3. Podell ER, Harrington DJ, Taatjes DJ, Koch TH: Crystal structure of epidoxorubicin-formaldehyde virtual crosslink of DNA and evidence for its formation in human breast-cancer cells. Acta Crystallogr D Biol Crystallogr. 1999 Sep;55(Pt 9):1516-23. [PubMed:10489446]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Innocenti F, Iyer L, Ramirez J, Green MD, Ratain MJ: Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7. Drug Metab Dispos. 2001 May;29(5):686-92. [PubMed:11302935]
  2. Zaya MJ, Hines RN, Stevens JC: Epirubicin glucuronidation and UGT2B7 developmental expression. Drug Metab Dispos. 2006 Dec;34(12):2097-101. Epub 2006 Sep 19. [PubMed:16985101]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phospholipase a2 activity
Specific Function
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory...
Gene Name
PLA2G4A
Uniprot ID
P47712
Uniprot Name
Cytosolic phospholipase A2
Molecular Weight
85238.2 Da
References
  1. Grataroli R, Leonardi J, Chautan M, Lafont H, Nalbone G: Effect of anthracyclines on phospholipase A2 activity and prostaglandin E2 production in rat gastric mucosa. Biochem Pharmacol. 1993 Aug 3;46(3):349-55. [PubMed:8347160]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Godinot N, Iversen PW, Tabas L, Xia X, Williams DC, Dantzig AH, Perry WL 3rd: Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. Mol Cancer Ther. 2003 Mar;2(3):307-16. [PubMed:12657726]
  2. Nunoya K, Grant CE, Zhang D, Cole SP, Deeley RG: Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26. [PubMed:12867490]
  3. Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595]

Drug created on June 13, 2005 07:24 / Updated on July 16, 2018 21:13