You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameEpirubicin
Accession NumberDB00445  (APRD00361)
TypeSmall Molecule
GroupsApproved
DescriptionAn 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 Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EllenceInjection, solution2 mg/mLIntravenousPharmacia And Upjohn Company Llc1999-09-15Not applicableUs
EllenceInjection, solution2 mg/mLIntravenousPharmacia And Upjohn Company Llc1999-09-15Not applicableUs
EpirubicinSolution2 mgIntravenousPfizer Canada Inc2014-06-05Not applicableCanada
Epirubicin for InjectionSolution2 mgIntravenousTeva Canada Limited2009-09-14Not applicableCanada
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousGreenstone, Llc1999-09-15Not applicableUs
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousGreenstone, Llc1999-09-15Not applicableUs
Epirubicin Hydrochloride for InjectionPowder, for solution50 mgIntravenousHospira Healthcare Corporation2008-04-07Not applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousUman Pharma IncNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2.0 mgIntravenousFresenius Kabi Canada Ltd2009-03-24Not applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousPharmaceutical Partners Of Canada IncNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousAccord Healthcare Inc2008-11-282012-10-03Canada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousHospira Healthcare Corporation2008-11-24Not applicableCanada
Epirubicin Hydrochloride InjectionSolution2 mgIntravenousOmega Laboratories LtdNot applicableNot applicableCanada
Pharmorubicin PFSSolution2 mgIntravenousPfizer Canada Inc1995-12-31Not applicableCanada
Pharmorubicin RdfPowder, for solution10 mgIntravenousPfizer Canada Inc1995-12-312006-08-02Canada
Pharmorubicin RdfPowder, for solution50 mgIntravenousPfizer Canada Inc1995-12-312006-08-02Canada
Pharmorubicin Rdf Inj 50mg/vialPowder, for solution50 mgIntravenousAdria Laboratories Of Canada Ltd.1985-12-311996-09-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Epirubicin HydrochlorideInjection50 mg/25mLIntravenousMylan Institutional LLC2013-07-31Not applicableUs
Epirubicin HydrochlorideInjection, solution50 mg/25mLIntravenousTeva Parenteral Medicines, Inc.2007-08-09Not applicableUs
Epirubicin HydrochlorideInjection2 mg/mLIntravenousActavis Pharma, Inc.2011-11-28Not applicableUs
Epirubicin HydrochlorideInjection50 mg/25mLIntravenousAmneal Agila, Llc2013-07-31Not applicableUs
Epirubicin HydrochlorideInjection200 mg/100mLIntravenousMylan Institutional LLC2013-07-31Not applicableUs
Epirubicin HydrochlorideInjection, solution200 mg/100mLIntravenousTeva Parenteral Medicines, Inc.2007-08-09Not applicableUs
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousHospira Worldwide, Inc.2007-04-19Not applicableUs
Epirubicin HydrochlorideInjection2 mg/mLIntravenousAreva Pharmaceuticals,Inc.2012-07-16Not applicableUs
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousSagent Pharmaceuticals2014-08-31Not applicableUs
Epirubicin HydrochlorideInjection, solution2 mg/mLIntravenousSandoz Inc2009-12-22Not applicableUs
Epirubicin HydrochlorideInjection2 mg/mLIntravenousImpax Generics2016-09-21Not applicableUs
Epirubicin HydrochlorideInjection200 mg/100mLIntravenousAmneal Agila, Llc2013-07-31Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Epirubicin EbeweNot Available
PharmorubicinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Epirubicin hydrochloride
ThumbNot applicableDBSALT001168
Categories
UNII3Z8479ZZ5X
CAS number56420-45-2
WeightAverage: 543.5193
Monoisotopic: 543.174060775
Chemical FormulaC27H29NO11
InChI KeyAOJJSUZBOXZQNB-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[[email protected]]3C[[email protected]](N)[C@@H](O)[[email protected]](C)O3)C(=O)CO)C(O)=C1C2=O
Pharmacology
IndicationFor use as a component of adjuvant therapy in patients with evidence of axillary node tumor involvement following resection of primary breast cancer.
Structured Indications
PharmacodynamicsEpirubicin 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 actionEpirubicin 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Chromodomain-helicase-DNA-binding protein 1Proteinyes
antagonist
HumanO14646 details
DNA topoisomerase 2-alphaProteinunknown
inhibitor
HumanP11388 details
DNANucleotideunknown
intercalation
Humannot applicabledetails
Related Articles
Absorption100%
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 binding77%
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 eliminationEpirubicin and its major metabolites are eliminated through biliary excretion and, to a lesser extent, by urinary excretion.
Half lifeHalf-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]
Toxicitybone marrow aplasia, grade 4 mucositis, and gastrointestinal bleeding
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
AcetovanilloneAcetovanillone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Epirubicin.Approved
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
Alendronic acidEpirubicin may increase the hypocalcemic activities of Alendronic acid.Approved
ALT-110The risk or severity of adverse effects can be increased when Epirubicin is combined with ALT-110.Investigational
AmdinocillinThe serum concentration of Epirubicin can be decreased when it is combined with Amdinocillin.Withdrawn
AmoxicillinThe serum concentration of Epirubicin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Epirubicin.Approved, Investigational
AmpicillinThe serum concentration of Epirubicin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AnisodamineAnisodamine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Epirubicin.Investigational
ApremilastApremilast may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Atracurium besylateEpirubicin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Epirubicin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Epirubicin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Epirubicin can be decreased when it is combined with Bacampicillin.Approved
BalsalazideBalsalazide may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Epirubicin.Investigational
BenoxaprofenBenoxaprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Epirubicin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzylpenicillinThe serum concentration of Epirubicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicillin PotassiumThe serum concentration of Epirubicin can be decreased when it is combined with Benzylpenicillin Potassium.Approved
Benzylpenicilloyl PolylysineThe serum concentration of Epirubicin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
Betulinic AcidBetulinic Acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
Botulinum Toxin Type AEpirubicin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BEpirubicin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Epirubicin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Epirubicin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Epirubicin.Approved
CarbenicillinThe serum concentration of Epirubicin can be decreased when it is combined with Carbenicillin.Approved
CarboplatinEpirubicin may increase the ototoxic activities of Carboplatin.Approved
CarindacillinThe serum concentration of Epirubicin can be decreased when it is combined with Carindacillin.Approved
CarprofenCarprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Experimental
CDX-110The risk or severity of adverse effects can be increased when Epirubicin is combined with CDX-110.Investigational
CelecoxibCelecoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
CimetidineThe serum concentration of Epirubicin can be increased when it is combined with Cimetidine.Approved
Cisatracurium besylateEpirubicin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Epirubicin.Approved
ClodronateEpirubicin may increase the hypocalcemic activities of Clodronate.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Epirubicin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Clozapine.Approved
ColistimethateEpirubicin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Epirubicin can be decreased when it is combined with Cyclacillin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
CyclosporineEpirubicin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
DecamethoniumEpirubicin may increase the respiratory depressant activities of Decamethonium.Approved
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
DiclofenacDiclofenac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Epirubicin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DiflunisalDiflunisal may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Epirubicin.Approved
DigoxinDigoxin 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
Domoic AcidEpirubicin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideEpirubicin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
E6201E6201 may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
EbselenEbselen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
EpirizoleEpirizole may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Epirubicin.Approved
EtanerceptEtanercept may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Etidronic acidEpirubicin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
EtoricoxibEtoricoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
exisulindexisulind may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
FenbufenFenbufen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
FingolimodEpirubicin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FloctafenineFloctafenine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Epirubicin can be decreased when it is combined with Flucloxacillin.Approved
FlunixinFlunixin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Vet Approved
FlurbiprofenFlurbiprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Epirubicin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Epirubicin.Approved, Vet Approved
G17DTThe risk or severity of adverse effects can be increased when Epirubicin is combined with G17DT.Investigational
Gallamine TriethiodideEpirubicin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GI-5005The risk or severity of adverse effects can be increased when Epirubicin is combined with GI-5005.Investigational
HigenamineHigenamine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
HMPL-004HMPL-004 may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
IbandronateEpirubicin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
IndomethacinIndomethacin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
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
IsoxicamIsoxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Epirubicin is combined with Leflunomide.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
LornoxicamLornoxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
LoxoprofenLoxoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
LumiracoxibLumiracoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Epirubicin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
MecamylamineEpirubicin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Epirubicin.Withdrawn
MeticillinThe serum concentration of Epirubicin can be decreased when it is combined with Meticillin.Approved
MetocurineEpirubicin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideEpirubicin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Epirubicin can be decreased when it is combined with Mezlocillin.Approved
MivacuriumEpirubicin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
NafcillinThe serum concentration of Epirubicin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
NatalizumabThe risk or severity of adverse effects can be increased when Epirubicin is combined with Natalizumab.Approved, Investigational
NCX 4016NCX 4016 may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
NeosaxitoxinEpirubicin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
Niflumic AcidNiflumic Acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
OlopatadineOlopatadine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Epirubicin which could result in a higher serum level.Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Epirubicin.Approved
OxacillinThe serum concentration of Epirubicin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Epirubicin.Approved, Vet Approved
PamidronateEpirubicin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumEpirubicin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
PhenoxymethylpenicillinThe serum concentration of Epirubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Epirubicin.Approved, Investigational
PipecuroniumEpirubicin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Epirubicin can be decreased when it is combined with Piperacillin.Approved
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Epirubicin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
PiroxicamPiroxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
PivampicillinThe serum concentration of Epirubicin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Epirubicin can be decreased when it is combined with Pivmecillinam.Approved
Procaine benzylpenicillinThe serum concentration of Epirubicin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
PropacetamolPropacetamol may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
PTC299PTC299 may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
PyrantelEpirubicin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Epirubicin is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Epirubicin.Approved
RapacuroniumEpirubicin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Epirubicin which could result in a higher serum level.Experimental, Investigational
RisedronateEpirubicin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumEpirubicin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational, Withdrawn
RoflumilastRoflumilast may increase the immunosuppressive activities of Epirubicin.Approved
SalicylamideSalicylamide may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
SeratrodastSeratrodast may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Epirubicin.Approved
SRP 299The risk or severity of adverse effects can be increased when Epirubicin is combined with SRP 299.Investigational
SRT501SRT501 may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
SuccinylcholineEpirubicin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Epirubicin can be decreased when it is combined with Sulbactam.Approved
SulfasalazineSulfasalazine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Epirubicin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Withdrawn
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Epirubicin.Approved, Investigational
TazobactamThe serum concentration of Epirubicin can be decreased when it is combined with Tazobactam.Approved
Technetium tc 99m etidronateEpirubicin may increase the hypocalcemic activities of Technetium tc 99m etidronate.Approved
Technetium Tc-99m MedronateEpirubicin may increase the hypocalcemic activities of Technetium Tc-99m Medronate.Approved
TenofovirThe serum concentration of Epirubicin can be increased when it is combined with Tenofovir.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TG4010The risk or severity of adverse effects can be increased when Epirubicin is combined with TG4010.Investigational
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Epirubicin can be decreased when it is combined with Ticarcillin.Approved, Vet Approved
TiludronateEpirubicin may increase the hypocalcemic activities of Tiludronate.Approved, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational
TofacitinibEpirubicin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Epirubicin.Approved
TranilastTranilast may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Epirubicin.Approved, Investigational
Trisalicylate-cholineTrisalicylate-choline may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
TubocurarineEpirubicin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Epirubicin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Epirubicin.Approved
VecuroniumEpirubicin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
ZileutonZileuton may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidEpirubicin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Epirubicin which could result in a higher serum level.Withdrawn
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 ReferencesNot Available
External Links
ATC CodesL01DB03
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (92.7 KB)
MSDSNot Available
ADMET
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 )
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
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
SolutionIntravenous2.0 mg
SolutionIntravenous2 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point344.53 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAnthracyclines
Sub ClassNot Available
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracyclinone-skeleton
  • Anthracycline
  • Tetracenequinone
  • 1,4-anthraquinone
  • 9,10-anthraquinone
  • Anthracene
  • Amino sugar
  • Tetralin
  • Aryl ketone
  • Hydroquinone
  • Anisole
  • Amino saccharide
  • Alkyl aryl ether
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

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 transcription. Also required for efficient transcription by RNA polymerase I, and more specifically the polymerase I transcription termination step. Regulates negatively DNA replication. Not only involved in ...
Gene Name:
CHD1
Uniprot ID:
O14646
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 segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
Gene Name:
TOP2A
Uniprot ID:
P11388
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 suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
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 response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
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, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23