Identification

Name
Daunorubicin
Accession Number
DB00694  (APRD00521)
Type
Small Molecule
Groups
Approved
Description

A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]

Structure
Thumb
Synonyms
  • (+)-Daunomycin
  • (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
  • Acetyladriamycin
  • Daunomycin
  • Daunorubicin
  • Daunorubicina
  • Daunorubicine
  • Daunorubicinum
  • Leukaemomycin C
  • Rubidomycin
External IDs
DNR / FI 6339 / NSC 82151 / RCRA Waste No. U059 / RP 13057
Product Ingredients
IngredientUNIICASInChI Key
Daunorubicin citrate5L84T2Z6NP371770-68-2VNTHYLVDGVBPOU-QQYBVWGSSA-N
Daunorubicin HydrochlorideUD984I04LZ23541-50-6GUGHGUXZJWAIAS-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cerubidine 20mg/vialPowder, for solution20 mgIntravenousErfa Canada 2012 Inc1971-12-31Not applicableCanada
Daunorubicin Hydrochloride for InjectionPowder, for solution20 mgIntravenousTeva1998-03-04Not applicableCanada
DaunoXomeInjection, lipid complex2 mg/mLIntravenousGalen US Inc2012-02-132016-10-13Us
Daunoxome Liposomal - IV 2mg/ml, 50mg/vialSuspension2 mgIntravenousGilead Sciences1997-09-222001-09-21Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Daunorubicin HydrochlorideInjection, solution5 mg/mLIntravenousTeva Parenteral Medicines, Inc.2004-04-01Not applicableUs
Daunorubicin HydrochlorideInjection5 mg/mLIntravenousWest Ward Pharmaceutical2018-01-02Not applicableUs
Daunorubicin HydrochlorideInjection5 mg/mLIntravenousWest Ward Pharmaceutical2018-01-02Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
VyxeosDaunorubicin (44 mg/20mL) + Cytarabine (100 mg/20mL)Injection, powder, lyophilized, for suspensionIntravenousJazz Pharmaceuticals2017-08-03Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Daunorubicin HydrochlorideDaunorubicin Hydrochloride (20 mg/4mL)Injection, powder, for solutionIntravenousHalison Pharmaceuiticals Usa, Inc2016-10-012018-05-26Us
International/Other Brands
Cerubidin (Sanofi-Aventis) / Cerubidine (Sanofi-Aventis) / Cérubidine (Sanofi-Aventis) / Daunoblastin (Pfizer) / Daunoblastina (Pfizer) / Daunorrubicina (GP-Pharm) / Maxidauno (Varifarma)
Categories
UNII
ZS7284E0ZP
CAS number
20830-81-3
Weight
Average: 527.5199
Monoisotopic: 527.179146153
Chemical Formula
C27H29NO10
InChI Key
STQGQHZAVUOBTE-VGBVRHCVSA-N
InChI
InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
IUPAC Name
(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-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(C)=O)C(O)=C1C2=O

Pharmacology

Indication

For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.

Associated Conditions
Pharmacodynamics

Daunorubicin 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. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.

Mechanism of action

Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin 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.

TargetActionsOrganism
ADNA
intercalation
Human
ADNA topoisomerase 2-alpha
inhibitor
Human
ADNA topoisomerase 2-beta
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

97% binding-albumin

Metabolism

Hepatic

Route of elimination

Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.

Half life

18.5 hours

Clearance
Not Available
Toxicity

LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1B1---(G;G) / (C;G)G alleleADR Directly StudiedThe presence of this genotype in CYP1B1 may be associated with an increased risk of drug-induced cytotoxicity from daunorubicin therapy.Details
Heterogeneous nuclear ribonucleoprotein D0---(A;A) / (A;G)A alleleADR Directly StudiedThe presence of this genotype in HNRNPD may be associated with an increased risk of drug-induced cytotoxicity from daunorubicin therapy.Details
SEC14-like protein 3---(T;T) / (G;T)T alleleADR Directly StudiedThe presence of this genotype in SEC14L3 may be associated with an increased risk of drug-induced cytotoxicity from daunorubicin therapy.Details
Inhibitor of nuclear factor kappa-B kinase subunit epsilon---(A;A) / (A;G)A alleleADR Directly StudiedThe presence of this genotype in IKBKE may be associated with an increased risk of drug-induced cytotoxicity from daunorubicin therapy.Details
Retinoic acid receptor gamma---(C;C) / (C;T)C>TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with daunorubicin.Details
Solute carrier family 28 member 3---(A;A) / (A;G)G > AADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with daunorubicin.Details
UDP-glucuronosyltransferase 1-6UGT1A6*4(T;T) / (G;T)G > TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with daunorubicin.Details

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Daunorubicin can be increased when it is combined with Abiraterone.Approved
Acetyl sulfisoxazoleThe metabolism of Daunorubicin can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Daunorubicin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Daunorubicin.Experimental
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Daunorubicin.Approved
AmiodaroneThe metabolism of Daunorubicin can be decreased when combined with Amiodarone.Approved, Investigational
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Daunorubicin.Approved, Investigational, Withdrawn
Anthrax immune globulin humanThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Anthrax immune globulin human.Approved
ApalutamideThe serum concentration of Daunorubicin can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Daunorubicin can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Daunorubicin.Approved, Investigational
AsunaprevirThe serum concentration of Asunaprevir can be decreased when it is combined with Daunorubicin.Approved, Investigational, Withdrawn
AtazanavirThe metabolism of Daunorubicin can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Daunorubicin can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Atorvastatin.Approved
AzithromycinThe metabolism of Daunorubicin can be decreased when combined with Azithromycin.Approved
Bacillus calmette-guerin substrain connaught live antigenThe risk or severity of adverse effects can be increased when Daunorubicin 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 Daunorubicin 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 Daunorubicin.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Daunorubicin.Approved, Investigational
BoceprevirThe metabolism of Daunorubicin can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Daunorubicin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Daunorubicin can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Daunorubicin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Daunorubicin.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Daunorubicin.Approved, Investigational
BupropionThe serum concentration of Daunorubicin can be increased when it is combined with Bupropion.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Daunorubicin.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Daunorubicin.Approved
CaffeineThe metabolism of Daunorubicin can be decreased when combined with Caffeine.Approved
CarbamazepineThe metabolism of Daunorubicin can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Daunorubicin can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Daunorubicin.Approved, Withdrawn
CitalopramThe metabolism of Daunorubicin can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Daunorubicin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Daunorubicin can be decreased when combined with Clemastine.Approved, Investigational
Clostridium tetani toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Daunorubicin is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated).Approved
ClotrimazoleThe metabolism of Daunorubicin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Clozapine.Approved
CobicistatThe metabolism of Daunorubicin can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Daunorubicin.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Daunorubicin.Approved, Investigational
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Daunorubicin is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated).Approved
CrizotinibThe metabolism of Daunorubicin can be decreased when combined with Crizotinib.Approved
CurcuminThe metabolism of Daunorubicin can be decreased when combined with Curcumin.Approved, Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Daunorubicin.Approved, Investigational
CyclosporineThe metabolism of Daunorubicin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Daunorubicin.Experimental
Cyproterone acetateThe serum concentration of Daunorubicin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Daunorubicin.Approved
DabrafenibThe serum concentration of Daunorubicin can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe metabolism of Daunorubicin can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Daunorubicin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Daunorubicin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Daunorubicin can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Daunorubicin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Daunorubicin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Daunorubicin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Daunorubicin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Daunorubicin.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Daunorubicin.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Daunorubicin.Approved, Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Daunorubicin.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Daunorubicin.Approved, Investigational
DiltiazemThe metabolism of Daunorubicin can be decreased when combined with Diltiazem.Approved, Investigational
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Daunorubicin.Approved, Investigational
DosulepinThe metabolism of Daunorubicin can be decreased when combined with Dosulepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Daunorubicin.Approved, Investigational
DoxycyclineThe metabolism of Daunorubicin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Daunorubicin can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Daunorubicin.Approved
EltrombopagThe serum concentration of Daunorubicin can be increased when it is combined with Eltrombopag.Approved
EnzalutamideThe serum concentration of Daunorubicin can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Daunorubicin.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Daunorubicin.Approved
ErythromycinThe metabolism of Daunorubicin can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Daunorubicin.Approved
FingolimodDaunorubicin may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe metabolism of Daunorubicin can be decreased when combined with Fluconazole.Approved, Investigational
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Daunorubicin.Approved
FluvoxamineThe metabolism of Daunorubicin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Daunorubicin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Daunorubicin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Daunorubicin can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Daunorubicin can be increased when it is combined with Fusidic Acid.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Daunorubicin is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Daunorubicin is combined with GI-5005.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Daunorubicin.Experimental
Hepatitis A VaccineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Hepatitis A Vaccine.Approved
Hepatitis B Vaccine (Recombinant)The risk or severity of adverse effects can be increased when Daunorubicin is combined with Hepatitis B Vaccine (Recombinant).Approved, Withdrawn
Human rabies virus immune globulinThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Human rabies virus immune globulin.Approved
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Daunorubicin.Approved
IdelalisibThe metabolism of Daunorubicin can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Daunorubicin can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Daunorubicin can be decreased when combined with Indinavir.Approved
INGN 201The risk or severity of adverse effects can be increased when Daunorubicin is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Daunorubicin is combined with INGN 225.Investigational
IsavuconazoleThe serum concentration of Daunorubicin can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Daunorubicin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Daunorubicin can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Daunorubicin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Daunorubicin can be increased when it is combined with Ivacaftor.Approved
Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Daunorubicin is combined with Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated).Approved
KetoconazoleThe metabolism of Daunorubicin can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Daunorubicin.Experimental
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Daunorubicin.Approved
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Daunorubicin.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Daunorubicin can be decreased when combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Daunorubicin.Approved
LipegfilgrastimDaunorubicin may increase the myelosuppressive activities of Lipegfilgrastim.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Daunorubicin.Approved, Investigational
LobeglitazoneThe metabolism of Daunorubicin can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Daunorubicin can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Daunorubicin can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Daunorubicin.Approved, Investigational
LuliconazoleThe serum concentration of Daunorubicin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Daunorubicin can be decreased when it is combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Daunorubicin.Illicit, Investigational, Withdrawn
MetamizoleThe risk or severity of myelosuppression can be increased when Metamizole is combined with Daunorubicin.Approved, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Daunorubicin.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Daunorubicin.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Daunorubicin.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Daunorubicin.Experimental
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Daunorubicin.Experimental
MexiletineThe metabolism of Daunorubicin can be decreased when combined with Mexiletine.Approved, Investigational
MidostaurinThe metabolism of Daunorubicin can be decreased when combined with Midostaurin.Approved, Investigational
MifepristoneThe serum concentration of Daunorubicin can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Daunorubicin can be decreased when it is combined with Mitotane.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Daunorubicin.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Natalizumab.Approved, Investigational
NefazodoneThe metabolism of Daunorubicin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Daunorubicin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Daunorubicin can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Daunorubicin can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Daunorubicin.Approved, Investigational
NilotinibThe metabolism of Daunorubicin can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Daunorubicin.Approved
OcrelizumabOcrelizumab may increase the immunosuppressive activities of Daunorubicin.Approved, Investigational
OlaparibThe metabolism of Daunorubicin can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Daunorubicin.Experimental, Investigational
OsimertinibThe serum concentration of Daunorubicin can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Daunorubicin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Daunorubicin.Approved, Vet Approved
PalbociclibThe serum concentration of Daunorubicin can be increased when it is combined with Palbociclib.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Daunorubicin.Approved
Peginterferon alfa-2bThe serum concentration of Daunorubicin can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Daunorubicin can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Daunorubicin.Approved, Investigational, Vet Approved, Withdrawn
PeruvosidePeruvoside may decrease the cardiotoxic activities of Daunorubicin.Experimental
PhenobarbitalThe metabolism of Daunorubicin can be increased when combined with Phenobarbital.Approved, Investigational
PhenytoinThe metabolism of Daunorubicin can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Daunorubicin.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Daunorubicin.Approved
PitolisantThe serum concentration of Daunorubicin can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe metabolism of Daunorubicin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Daunorubicin.Approved
PrimidoneThe metabolism of Daunorubicin can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Daunorubicin.Experimental
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Daunorubicin.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Daunorubicin 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 Daunorubicin.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Daunorubicin.Approved, Investigational
RifabutinThe metabolism of Daunorubicin can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Daunorubicin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Daunorubicin can be increased when combined with Rifapentine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Daunorubicin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Daunorubicin.Approved
RindopepimutThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Rindopepimut.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Daunorubicin.Approved
RolapitantThe serum concentration of Daunorubicin can be increased when it is combined with Rolapitant.Approved, Investigational
RopiniroleThe metabolism of Daunorubicin can be decreased when combined with Ropinirole.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Daunorubicin.Approved
Rotavirus VaccineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Rotavirus Vaccine.Approved
Rubella virus vaccineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Rubella virus vaccine.Approved, Investigational
RucaparibThe metabolism of Daunorubicin can be decreased when combined with Rucaparib.Approved, Investigational
Salmonella typhi ty2 vi polysaccharide antigenThe risk or severity of adverse effects can be increased when Daunorubicin 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 Daunorubicin is combined with Salmonella typhi ty21a live antigen.Approved
SaquinavirThe metabolism of Daunorubicin can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Daunorubicin can be decreased when used in combination with Sarilumab.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Daunorubicin.Approved
SildenafilThe metabolism of Daunorubicin can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Daunorubicin.Approved
SiltuximabThe serum concentration of Daunorubicin can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Daunorubicin can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Daunorubicin.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Daunorubicin.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Daunorubicin.Approved
SRP 299The risk or severity of adverse effects can be increased when Daunorubicin is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Daunorubicin can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Daunorubicin can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Daunorubicin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusTacrolimus may increase the immunosuppressive activities of Daunorubicin.Approved, Investigational
TecemotideThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Tecemotide.Investigational
TelaprevirThe metabolism of Daunorubicin can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Daunorubicin can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Daunorubicin.Experimental
TeriflunomideThe serum concentration of Daunorubicin can be decreased when it is combined with Teriflunomide.Approved
TG4010The risk or severity of adverse effects can be increased when Daunorubicin is combined with TG4010.Investigational
TheophyllineThe metabolism of Daunorubicin can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Daunorubicin can be decreased when combined with Ticlopidine.Approved
TipiracilThe serum concentration of Tipiracil can be increased when it is combined with Daunorubicin.Approved, Investigational
TocilizumabThe serum concentration of Daunorubicin can be decreased when it is combined with Tocilizumab.Approved
TofacitinibDaunorubicin may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Daunorubicin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Daunorubicin.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Daunorubicin.Approved, Investigational
Typhoid VaccineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Typhoid Vaccine.Approved
Varicella Zoster Vaccine (Live/Attenuated)The risk or severity of adverse effects can be increased when Daunorubicin is combined with Varicella Zoster Vaccine (Live/Attenuated).Approved
VemurafenibThe serum concentration of Daunorubicin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Daunorubicin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Daunorubicin can be decreased when combined with Verapamil.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Daunorubicin.Approved, Investigational
VoriconazoleThe metabolism of Daunorubicin can be decreased when combined with Voriconazole.Approved, Investigational
Yellow Fever VaccineThe risk or severity of adverse effects can be increased when Daunorubicin is combined with Yellow Fever Vaccine.Approved, Investigational
ZiprasidoneThe metabolism of Daunorubicin can be decreased when combined with Ziprasidone.Approved
ZucapsaicinThe metabolism of Daunorubicin can be decreased when combined with Zucapsaicin.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Sylvie Pinnert, Leon Ninet, Jean Preud'Homme, "Antibiotic daunorubicin and its preparation." U.S. Patent US3989598, issued March, 1965.

US3989598
General References
Not Available
External Links
Human Metabolome Database
HMDB0014832
KEGG Compound
C01907
PubChem Compound
30323
PubChem Substance
46508433
ChemSpider
28163
BindingDB
32017
ChEBI
41977
ChEMBL
CHEMBL178
Therapeutic Targets Database
DNC000517
PharmGKB
PA449212
HET
DM1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Daunorubicin
ATC Codes
L01DB02 — Daunorubicin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
110d / 152d / 1d10 / 1d11 / 1d33 / 1da0 / 1jo2 / 1o0k / 1vth / 1vti
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MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAdvanced Myelodysplastic Syndrome / Leukemia Acute Myeloid Leukemia (AML)1
1Active Not RecruitingTreatmentBlasts 10-19 Percent of Bone Marrow Nucleated Cells / Blasts 20 Percent or More of Bone Marrow Nucleated Cells / Blasts 5-19 Percent of Peripheral Blood White Cells / Chronic Myelomonocytic Leukemia-2 / Leukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndrome / Myeloproliferative Neoplasms / Previously Treated Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia1
1Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Leukemias1
1Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Malignancies, Hematologic1
1CompletedTreatmentAcute Myelogenous Leukaemia (AML) / Leukemia Acute Myeloid Leukemia (AML)1
1CompletedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
1CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)3
1CompletedTreatmentLeukemias3
1CompletedTreatmentMyelogenous Leukemia, Acute1
1Not Yet RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Lymphocytic Leukemia (ALL) / Leukemia Acute Myeloid Leukemia (AML) / Malignancies, Hematologic / Myelodysplastic Syndromes1
1Not Yet RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1RecruitingTreatmentAML Arising After Exposure to Genotoxic Injury / AML Arising From Antecedent Hematologic Disorder (AHD) / AML Arising From Myelodysplastic Syndrome (MDS) / Newly Diagnosed Acute Myeloid Leukemia (AML) / Untreated AML1
1RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
1RecruitingTreatmentAcute Lymphocytic Leukemia (ALL) / Leukemia Acute Myeloid Leukemia (AML)1
1RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)4
1RecruitingTreatmentRecurrent Adult Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Therapy-Related Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
1TerminatedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1TerminatedTreatmentLeukemias1
1TerminatedTreatmentSarcomas1
1Unknown StatusTreatmentLeukemias1
1, 2CompletedTreatmentAcute Undifferentiated Leukemia (AUL) / B-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / L1 Adult Acute Lymphoblastic Leukemia / L1 Childhood Acute Lymphoblastic Leukemia / L2 Adult Acute Lymphoblastic Leukemia / L2 Childhood Acute Lymphoblastic Leukemia / Philadelphia Chromosome Negative Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Childhood Precursor Acute Lymphoblastic Leukemia / T-cell Adult Acute Lymphoblastic Leukemia / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
1, 2CompletedTreatmentAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Leukemia Acute Myeloid Leukemia (AML) / Untreated Adult Acute Myeloid Leukemia1
1, 2CompletedTreatmentChronic Myelomonocytic Leukemia / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation1
1, 2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1, 2CompletedTreatmentLeukemias4
1, 2CompletedTreatmentMyeloid Leukemias1
1, 2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
1, 2RecruitingTreatmentPreviously Untreated Acute Myeloid Leukemia1
1, 2SuspendedTreatmentBlasts 5 Percent or More of Bone Marrow Nucleated Cells / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Therapy-Related Acute Myeloid Leukemia1
1, 2TerminatedTreatmentChronic Myeloid Leukemia (CML)1
1, 2WithdrawnTreatmentUntreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Adult B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / Adult B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Untreated Adult Acute Lymphoblastic Leukemia1
2Active Not RecruitingTreatmentAcute Myeloid Leukemia (Megakaryoblastic) With t(1;22)(p13.3;q13.3); RBM15-MKL1 / Acute Myeloid Leukemia (Megakaryoblastic) With t(1;22)(p13;q13); RBM15-MKL1 / Acute Myeloid Leukemia With a Variant RARA Translocation / Acute Myeloid Leukemia With Inv(3) (q21.3;q26.2) or t(3;3) (q21.3;q26.2); GATA2, MECOM / Acute Myeloid Leukemia With Inv(3)(q21q26.2) or t(3;3)(q21;q26.2); RPN1-EVI1 / Acute Myeloid Leukemia With t(6;9) (p23;q34.1); DEK-NUP214 / Acute Myeloid Leukemia With t(6;9)(p23;q34); DEK-NUP214 / Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Acute Myeloid Leukemia With Variant MLL Translocations / Leukemia Acute Myeloid Leukemia (AML) / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAcute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1 / Core Binding Factor Acute Myeloid Leukemia / Leukemia Acute Myeloid Leukemia (AML) / Secondary Acute Myeloid Leukemia / Therapy-Related Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAcute Myeloid Leukemia With Myelodysplasia-Related Changes / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With t(8;21)(q22;q22); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Leukemia Acute Myeloid Leukemia (AML) / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentAdult Acute Basophilic Leukemia / Adult Acute Eosinophilic Leukemia / Adult Acute Monoblastic Leukemia / Adult Acute Monocytic Leukemia / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Adult Acute Myeloid Leukemia With t(9;11)(p22;q23); MLLT3-MLL / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Alkylating Agent-Related Acute Myeloid Leukemia / Leukemia Acute Myeloid Leukemia (AML) / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
2Active Not RecruitingTreatmentLeukaemia, Lymphoblastic / Lymphoma, Lymphoblastic1
2Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)3
2Active Not RecruitingTreatmentLeukemias1
2Active Not RecruitingTreatmentLymphoma, Lymphoblastic1
2Active Not RecruitingTreatmentNewly Diagnosed AML With FLT3 Activating Mutations1
2Active Not RecruitingTreatmentUntreated Adult Acute Myeloid Leukemia1
2CompletedNot AvailableAcute Myelogenous Leukaemia (AML)1
2CompletedBasic ScienceLeukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndromes / Myeloproliferative Neoplasms / Myeloproliferative/Myelodysplastic Neoplasm1
2CompletedSupportive CareAnemias / Leukemias / Neutropenias / Thrombocytopenias1
2CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL)2
2CompletedTreatmentAcute Lymphocytic Leukemia (ALL)1
2CompletedTreatmentAcute Myeloid Leukemia With Multilineage Dysplasia Following Myelodysplastic Syndrome / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
2CompletedTreatmentLeukaemia, Acute1
2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)3
2CompletedTreatmentLeukemias15
2CompletedTreatmentLeukemias / Malignant Lymphomas2
2CompletedTreatmentLeukemias / Neutropenias / Thrombocytopenias1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1
2Enrolling by InvitationTreatmentAcute,Leukemia, Lymphoid1
2Not Yet RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Childhood Cancers / Down Syndrome (DS)1
2RecruitingTreatmentAcute Leukemias of Ambiguous Lineage / Childhood B Acute Lymphoblastic Leukemia / KMT2A Gene Rearrangement / Mixed Phenotype Acute Leukemia (MPAL)1
2RecruitingTreatmentAcute Lymphocytic Leukemia (ALL) / Adult Lymphoblastic Lymphoma1
2RecruitingTreatmentAll1
2RecruitingTreatmentLeukaemia, Lymphoblastic1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndromes1
2RecruitingTreatmentLeukemias1
2RecruitingTreatmentUntreated Adult Acute Myeloid Leukemia1
2TerminatedTreatmentHigh-risk Myelodysplastic Syndrome (MDS) / Leukemia Acute Myeloid Leukemia (AML)1
2TerminatedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2TerminatedTreatmentLeukemias1
2TerminatedTreatmentLeukemias / Lymphoma, Lymphoblastic / Malignant Lymphomas / Precursor-B Acute Lymphoblastic Leukemia1
2Unknown StatusTreatmentLeukemias2
2, 3Active Not RecruitingTreatmentMyeloid Leukemias1
2, 3CompletedTreatmentAdult B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Childhood B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
2, 3CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2, 3CompletedTreatmentLeukemias / Myelodysplastic Syndromes1
2, 3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Lymphoblastic Lymphoma1
2, 3RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2, 3RecruitingTreatmentLeukemias1
2, 3RecruitingTreatmentLymphoma, Lymphoblastic1
2, 3Unknown StatusTreatmentDe Novo Akute Myeloid Leukemia (AML) / Refractory Anemia With Excess of Blasts in Transformation / Secondary Acute Myeloid Leukemia (AML)1
2, 3Unknown StatusTreatmentLeukemias1
3Active Not RecruitingTreatmentAcute Myeloid Leukemia With Multilineage Dysplasia Following Myelodysplastic Syndrome / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
3Active Not RecruitingTreatmentAcute Undifferentiated Leukemia (AUL) / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3Active Not RecruitingTreatmentChildhood Acute Basophilic Leukemia / Childhood Acute Eosinophilic Leukemia / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myelomonocytic Leukemia (M4) / Childhood Myelodysplastic Syndromes / De Novo Myelodysplastic Syndromes / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3Active Not RecruitingTreatmentGranulocytic Sarcoma / Leukaemia cutis / Leukemia Acute Myeloid Leukemia (AML) / Myeloid Neoplasm / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Myeloid Neoplasm1
3Active Not RecruitingTreatmentHigh Risk Acute Myeloid Leukemia1
3Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
3Active Not RecruitingTreatmentLeukemias4
3Active Not RecruitingTreatmentLymphoblastic Leukemia, Acute1
3Active Not RecruitingTreatmentMalignant Lymphomas1
3CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Adult T Acute Lymphoblastic Leukemia / Ann Arbor Stage II Adult T-Cell Leukemia/Lymphoma / Ann Arbor Stage II Childhood Lymphoblastic Lymphoma / Ann Arbor Stage II Contiguous Adult Lymphoblastic Lymphoma / Ann Arbor Stage II Non-Contiguous Adult Lymphoblastic Lymphoma / Ann Arbor Stage III Adult Lymphoblastic Lymphoma / Ann Arbor Stage III Adult T-Cell Leukemia/Lymphoma / Ann Arbor Stage III Childhood Lymphoblastic Lymphoma / Ann Arbor Stage IV Adult Lymphoblastic Lymphoma / Ann Arbor Stage IV Adult T-Cell Leukemia/Lymphoma / Ann Arbor Stage IV Childhood Lymphoblastic Lymphoma / Childhood T Acute Lymphoblastic Leukemia / Stage II Adult T-Cell Leukemia/Lymphoma / Stage II Childhood Lymphoblastic Lymphoma / Stage II Contiguous Adult Lymphoblastic Lymphoma / Stage II Non-Contiguous Adult Lymphoblastic Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Adult T-Cell Leukemia/Lymphoma / Stage III Childhood Lymphoblastic Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Adult T-Cell Leukemia/Lymphoma / Stage IV Childhood Lymphoblastic Lymphoma / T Acute Lymphoblastic Leukemia / T Lymphoblastic Lymphoma / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3CompletedTreatmentAdult Acute Basophilic Leukemia / Adult Acute Eosinophilic Leukemia / Adult Acute Erythroid Leukemia (M6) / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monoblastic Leukemia and Acute Monocytic Leukemia (M5) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Childhood Acute Basophilic Leukemia / Childhood Acute Eosinophilic Leukemia / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monoblastic Leukemia and Acute Monocytic Leukemia (M5) / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myelomonocytic Leukemia (M4) / Childhood Myelodysplastic Syndromes / De Novo Myelodysplastic Syndromes / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3CompletedTreatmentAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Untreated Adult Acute Myeloid Leukemia1
3CompletedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
3CompletedTreatmentAdult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Promyelocytic Leukemia (M3) / Childhood Acute Promyelocytic Leukemia (M3) / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3CompletedTreatmentChildhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myelomonocytic Leukemia (M4) / Childhood Myelodysplastic Syndromes / Chronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndromes / Refractory Anemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation / Refractory Anemia With Ringed Sideroblasts / Secondary Myelodysplastic Syndromes / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3CompletedTreatmentChildhood Acute Lymphoblastic Leukemia in Remission / Recurrent Childhood Acute Lymphoblastic Leukemia1
3CompletedTreatmentElderly / Leukemia Acute Myeloid Leukemia (AML)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
3CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)5
3CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML) / Untreated Adult Acute Myeloid Leukemia1
3CompletedTreatmentLeukemia, Myelocytic, Acute1
3CompletedTreatmentLeukemias12
3CompletedTreatmentLeukemias / Malignant Lymphomas2
3CompletedTreatmentLeukemias / Myelodysplastic Syndromes4
3CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms3
3CompletedTreatmentSarcomas1
3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Adult B Acute Lymphoblastic Leukemia / B Acute Lymphoblastic Leukemia, Philadelphia Chromosome Negative / BCR/ABL1 Fusion Protein Negative / Untreated Adult Acute Lymphoblastic Leukemia1
3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / BCR-ABL1 Fusion Protein Expression / Minimal Residual Disease / Philadelphia Chromosome Positive / T Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Lymphoma, Lymphoblastic1
3RecruitingTreatmentChildhood Acute Myeloid Leukemia / Childhood Myelodysplastic Syndrome / Cytopenias / Down Syndrome (DS) / Myeloid Leukemia Associated With Down Syndrome / Myeloproliferative Neoplasms1
3RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)4
3RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Leukemias1
3RecruitingTreatmentLeukemias1
3SuspendedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Adult T Acute Lymphoblastic Leukemia / Ann Arbor Stage II Adult Lymphoblastic Lymphoma / Ann Arbor Stage II Childhood Lymphoblastic Lymphoma / Ann Arbor Stage III Adult Lymphoblastic Lymphoma / Ann Arbor Stage III Childhood Lymphoblastic Lymphoma / Ann Arbor Stage IV Adult Lymphoblastic Lymphoma / Ann Arbor Stage IV Childhood Lymphoblastic Lymphoma / Childhood T Acute Lymphoblastic Leukemia / Stage II Adult Lymphoblastic Lymphoma / Stage II Childhood Lymphoblastic Lymphoma / Stage II Contiguous Adult Lymphoblastic Lymphoma / Stage II Non-Contiguous Adult Lymphoblastic Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Childhood Lymphoblastic Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Childhood Lymphoblastic Lymphoma / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3SuspendedTreatmentB Acute Lymphoblastic Leukemia1
3TerminatedTreatmentAcute Lymphoblastic Leukaemias (ALL)1
3TerminatedTreatmentMalignant Lymphomas1
3Unknown StatusTreatmentLeukemias4
3Unknown StatusTreatmentLeukemias / Malignant Lymphomas1
3Unknown StatusTreatmentLeukemias / Mucositis / Oral Complications1
3Unknown StatusTreatmentLeukemias / Neutropenias1
3Unknown StatusTreatmentLymphoblastic Leukemia, Acute1
3Unknown StatusTreatmentMalignant Lymphomas2
3Unknown StatusTreatmentSecondary Acute Myeloid Leukemia (Secondary AML, sAML)1
3WithdrawnTreatmentLeukemias1
4Active Not RecruitingPreventionLeukemia Acute Myeloid Leukemia (AML)1
4Active Not RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
4CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL)4
4CompletedTreatmentAdult Acute Lymphocytic Leukemia3
4CompletedTreatmentLymphoma, Lymphoblastic1
4RecruitingTreatmentAcute Lymphobkastic Leukemia1
4RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
4Unknown StatusPreventionAcute Promyelocytic Leukemia (APL)1
4Unknown StatusTreatmentAdult Acute Lymphocytic Leukemia1
Not AvailableActive Not RecruitingTreatmentB-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
Not AvailableActive Not RecruitingTreatmentChildhood Acute Lymphoblastic Leukemia1
Not AvailableActive Not RecruitingTreatmentUnspecified Childhood Solid Tumor, Protocol Specific1
Not AvailableCompletedTreatmentAtaxia-Telangiectasia1
Not AvailableCompletedTreatmentB-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
Not AvailableCompletedTreatmentLeukemias3
Not AvailableCompletedTreatmentLymphoma, Lymphoblastic1
Not AvailableCompletedTreatmentT-cell Childhood Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
Not AvailableNot Yet RecruitingNot AvailableAcute Myeloid Leukemia With Myelodysplasia-Related Changes / Therapy-Related Acute Myeloid Leukemia1
Not AvailableRecruitingNot AvailableAdult Acute Lymphoblastic Leukemia1
Not AvailableRecruitingOtherLeukemia, Myelocytic, Acute1
Not AvailableRecruitingTreatmentChildhood Acute Lymphoblastic Leukemia1
Not AvailableRecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
Not AvailableUnknown StatusTreatmentLeukemias2
Not AvailableWithdrawnNot AvailableLeukemias1

Pharmacoeconomics

Manufacturers
  • Gilead sciences inc
  • Bedford laboratories div ben venue laboratories inc
  • Sanofi aventis us llc
  • Wyeth ayerst research
  • App pharmaceuticals llc
  • Teva parenteral medicines inc
Packagers
  • APP Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bigmar Bioren Pharmaceuticals Sa
  • Gilead Sciences Inc.
  • Sicor Pharmaceuticals
  • Specia Alfort
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
Powder, for solutionIntravenous20 mg
InjectionIntravenous5 mg/mL
Injection, powder, for solutionIntravenous20 mg/4mL
Injection, solutionIntravenous5 mg/mL
Injection, lipid complexIntravenous2 mg/mL
SuspensionIntravenous2 mg
Injection, powder, lyophilized, for suspensionIntravenous
Prices
Unit descriptionCostUnit
Daunorubicin 20 mg/4 ml vial163.01USD ml
Cerubidine 20 mg vial50.4USD vial
Daunorubicin 50 mg/10 ml vial42.45USD ml
Daunoxome 2 mg/ml vial13.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7850990No2007-01-232027-01-23Us
US8022279No2007-09-142027-09-14Us
US8431806No2005-04-222025-04-22Us
US8092828No2009-04-012029-04-01Us
US8518437No2006-06-072026-06-07Us
US9271931No2007-01-232027-01-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208-209 °CPhysProp
water solubility39.2 mg/LNot Available
logP1.83SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.627 mg/mLALOGPS
logP1.68ALOGPS
logP1.73ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area185.84 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity132.89 m3·mol-1ChemAxon
Polarizability52.94 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6524
Blood Brain Barrier-0.9869
Caco-2 permeable-0.7227
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.636
P-glycoprotein inhibitor IINon-inhibitor0.9136
Renal organic cation transporterNon-inhibitor0.9213
CYP450 2C9 substrateNon-substrate0.7987
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5951
CYP450 1A2 substrateInhibitor0.8777
CYP450 2C9 inhibitorNon-inhibitor0.9448
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9527
CYP450 3A4 inhibitorNon-inhibitor0.9157
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9543
Ames testAMES toxic0.9224
CarcinogenicityNon-carcinogens0.9521
BiodegradationNot ready biodegradable0.9844
Rat acute toxicity3.2275 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9888
hERG inhibition (predictor II)Non-inhibitor0.8916
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

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 12 more
Substituents
Anthracycline / Anthracyclinone-skeleton / Aminoglycoside core / Tetracenequinone / 9,10-anthraquinone / 1,4-anthraquinone / Anthracene / Hexose monosaccharide / Glycosyl compound / O-glycosyl compound
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinone, aminoglycoside antibiotic, anthracycline (CHEBI:41977) / Anthracyclinones (C01907) / Anthracyclinones (LMPK13050002)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
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. Aubel-Sadron G, Londos-Gagliardi D: Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review. Biochimie. 1984 May;66(5):333-52. [PubMed:6380596]
  2. Zunino F, Capranico G: DNA topoisomerase II as the primary target of anti-tumor anthracyclines. Anticancer Drug Des. 1990 Nov;5(4):307-17. [PubMed:1963303]
Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Aubel-Sadron G, Londos-Gagliardi D: Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review. Biochimie. 1984 May;66(5):333-52. [PubMed:6380596]
  2. Zunino F, Capranico G: DNA topoisomerase II as the primary target of anti-tumor anthracyclines. Anticancer Drug Des. 1990 Nov;5(4):307-17. [PubMed:1963303]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Protein kinase c binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks.
Gene Name
TOP2B
Uniprot ID
Q02880
Uniprot Name
DNA topoisomerase 2-beta
Molecular Weight
183265.825 Da
References
  1. Aubel-Sadron G, Londos-Gagliardi D: Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review. Biochimie. 1984 May;66(5):333-52. [PubMed:6380596]
  2. Zunino F, Capranico G: DNA topoisomerase II as the primary target of anti-tumor anthracyclines. Anticancer Drug Des. 1990 Nov;5(4):307-17. [PubMed:1963303]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Wang T, Chen FY, Han JY, Shao NX, Ou-Yuang RR: [Study of CYP3A5 in drug resistance mechanisms in acute leukemia]. Zhonghua Xue Ye Xue Za Zhi. 2003 Jun;24(6):286-9. [PubMed:12859862]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine oxidase activity
Specific Function
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. Yee SB, Pritsos CA: Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase. Arch Biochem Biophys. 1997 Nov 15;347(2):235-41. [PubMed:9367530]
  2. Yee SB, Pritsos CA: Reductive activation of doxorubicin by xanthine dehydrogenase from EMT6 mouse mammary carcinoma tumors. Chem Biol Interact. 1997 May 2;104(2-3):87-101. [PubMed:9212777]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Bachur NR, Gordon SL, Gee MV, Kon H: NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals. Proc Natl Acad Sci U S A. 1979 Feb;76(2):954-7. [PubMed:34156]
  2. Di Re J, Lee C, Riddick DS: Lack of mechanism-based inactivation of rat hepatic microsomal cytochromes P450 by doxorubicin. Can J Physiol Pharmacol. 1999 Aug;77(8):589-97. [PubMed:10543722]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Zhou G, Kuo MT: Wild-type p53-mediated induction of rat mdr1b expression by the anticancer drug daunorubicin. J Biol Chem. 1998 Jun 19;273(25):15387-94. [PubMed:9624121]
  2. Gao J, Murase O, Schowen RL, Aube J, Borchardt RT: A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. Pharm Res. 2001 Feb;18(2):171-6. [PubMed:11405287]
  3. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674]
  4. Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945]
  5. Takara K, Tanigawara Y, Komada F, Nishiguchi K, Sakaeda T, Okumura K: Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biol Pharm Bull. 1999 Dec;22(12):1355-9. [PubMed:10746169]
  6. Tang F, Ouyang H, Yang JZ, Borchardt RT: Bidirectional transport of rhodamine 123 and Hoechst 33342, fluorescence probes of the binding sites on P-glycoprotein, across MDCK-MDR1 cell monolayers. J Pharm Sci. 2004 May;93(5):1185-94. [PubMed:15067695]
  7. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684]
  8. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675]
  9. Takara K, Sakaeda T, Kakumoto M, Tanigawara Y, Kobayashi H, Okumura K, Ohnishi N, Yokoyama T: Effects of alpha-adrenoceptor antagonist doxazosin on MDR1-mediated multidrug resistance and transcellular transport. Oncol Res. 2009;17(11-12):527-33. [PubMed:19806783]
  10. Borska S, Sopel M, Chmielewska M, Zabel M, Dziegiel P: Quercetin as a potential modulator of P-glycoprotein expression and function in cells of human pancreatic carcinoma line resistant to daunorubicin. Molecules. 2010 Feb 9;15(2):857-70. doi: 10.3390/molecules15020857. [PubMed:20335952]
  11. Perez-Victoria JM, Chiquero MJ, Conseil G, Dayan G, Di Pietro A, Barron D, Castanys S, Gamarro F: Correlation between the affinity of flavonoids binding to the cytosolic site of Leishmania tropica multidrug transporter and their efficiency to revert parasite resistance to daunomycin. Biochemistry. 1999 Feb 9;38(6):1736-43. [PubMed:10026252]
  12. Pallis M, Turzanski J, Harrison G, Wheatley K, Langabeer S, Burnett AK, Russell NH: Use of standardized flow cytometric determinants of multidrug resistance to analyse response to remission induction chemotherapy in patients with acute myeloblastic leukaemia. Br J Haematol. 1999 Feb;104(2):307-12. [PubMed:10050713]
  13. Chiodini B, Bassan R, Barbui T: Cellular uptake and antiproliferative effects of therapeutic concentrations of idarubicin or daunorubicin and their alcohol metabolites, with or without cyclosporin A, in MDR1+ human leukemic cells. Leuk Lymphoma. 1999 May;33(5-6):485-97. [PubMed:10342576]
  14. Romsicki Y, Sharom FJ: The membrane lipid environment modulates drug interactions with the P-glycoprotein multidrug transporter. Biochemistry. 1999 May 25;38(21):6887-96. [PubMed:10346910]
  15. Hiessbock R, Wolf C, Richter E, Hitzler M, Chiba P, Kratzel M, Ecker G: Synthesis and in vitro multidrug resistance modulating activity of a series of dihydrobenzopyrans and tetrahydroquinolines. J Med Chem. 1999 Jun 3;42(11):1921-6. [PubMed:10354400]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Loe DW, Almquist KC, Cole SP, Deeley RG: ATP-dependent 17 beta-estradiol 17-(beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids. J Biol Chem. 1996 Apr 19;271(16):9683-9. [PubMed:8621644]
  2. Heijn M, Hooijberg JH, Scheffer GL, Szabo G, Westerhoff HV, Lankelma J: Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport. Biochim Biophys Acta. 1997 May 22;1326(1):12-22. [PubMed:9188796]
  3. Priebe W, Krawczyk M, Kuo MT, Yamane Y, Savaraj N, Ishikawa T: Doxorubicin- and daunorubicin-glutathione conjugates, but not unconjugated drugs, competitively inhibit leukotriene C4 transport mediated by MRP/GS-X pump. Biochem Biophys Res Commun. 1998 Jun 29;247(3):859-63. [PubMed:9647783]
  4. 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]
  5. 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]
  6. Versantvoort CH, Broxterman HJ, Lankelma J, Feller N, Pinedo HM: Competitive inhibition by genistein and ATP dependence of daunorubicin transport in intact MRP overexpressing human small cell lung cancer cells. Biochem Pharmacol. 1994 Sep 15;48(6):1129-36. [PubMed:7945406]
  7. Yazaki K, Yamanaka N, Masuno T, Konagai S, Shitan N, Kaneko S, Ueda K, Sato F: Heterologous expression of a mammalian ABC transporter in plant and its application to phytoremediation. Plant Mol Biol. 2006 Jun;61(3):491-503. [PubMed:16830181]
  8. 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]
  9. Nabekura T, Yamaki T, Hiroi T, Ueno K, Kitagawa S: Inhibition of anticancer drug efflux transporter P-glycoprotein by rosemary phytochemicals. Pharmacol Res. 2010 Mar;61(3):259-63. doi: 10.1016/j.phrs.2009.11.010. Epub 2009 Nov 26. [PubMed:19944162]
  10. Renes J, de Vries EG, Nienhuis EF, Jansen PL, Muller M: ATP- and glutathione-dependent transport of chemotherapeutic drugs by the multidrug resistance protein MRP1. Br J Pharmacol. 1999 Feb;126(3):681-8. [PubMed:10188979]
  11. Hooijberg JH, Pinedo HM, Vrasdonk C, Priebe W, Lankelma J, Broxterman HJ: The effect of glutathione on the ATPase activity of MRP1 in its natural membranes. FEBS Lett. 2000 Mar 3;469(1):47-51. [PubMed:10708754]
  12. Marbeuf-Gueye C, Salerno M, Quidu P, Garnier-Suillerot A: Inhibition of the P-glycoprotein- and multidrug resistance protein-mediated efflux of anthracyclines and calceinacetoxymethyl ester by PAK-104P. Eur J Pharmacol. 2000 Mar 17;391(3):207-16. [PubMed:10729360]
  13. Evers R, Kool M, Smith AJ, van Deemter L, de Haas M, Borst P: Inhibitory effect of the reversal agents V-104, GF120918 and Pluronic L61 on MDR1 Pgp-, MRP1- and MRP2-mediated transport. Br J Cancer. 2000 Aug;83(3):366-74. [PubMed:10917553]
  14. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name
ABCC10
Uniprot ID
Q5T3U5
Uniprot Name
Multidrug resistance-associated protein 7
Molecular Weight
161627.375 Da
References
  1. Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD: Human multidrug resistance protein 7 (ABCC10) is a resistance factor for nucleoside analogues and epothilone B. Cancer Res. 2009 Jan 1;69(1):178-84. doi: 10.1158/0008-5472.CAN-08-1420. [PubMed:19118001]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Isoform 1: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4...
Gene Name
ABCC6
Uniprot ID
O95255
Uniprot Name
Multidrug resistance-associated protein 6
Molecular Weight
164904.81 Da
References
  1. Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [PubMed:12414644]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759]
  2. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [PubMed:12668685]
  2. Ozvegy C, Litman T, Szakacs G, Nagy Z, Bates S, Varadi A, Sarkadi B: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7. [PubMed:11437380]
  3. Nakanishi T, Doyle LA, Hassel B, Wei Y, Bauer KS, Wu S, Pumplin DW, Fang HB, Ross DD: Functional characterization of human breast cancer resistance protein (BCRP, ABCG2) expressed in the oocytes of Xenopus laevis. Mol Pharmacol. 2003 Dec;64(6):1452-62. [PubMed:14645676]

Drug created on June 13, 2005 07:24 / Updated on June 24, 2018 11:36