Identification

Name
Valrubicin
Accession Number
DB00385  (APRD00662)
Type
Small Molecule
Groups
Approved
Description

Valrubicin (N-trifluoroacetyladriamycin-14-valerate, Valstar®) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. [Wikipedia]

Structure
Thumb
Synonyms
  • (8S, 10S)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-(2,2,2-trifluoroacetamido)-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione 8²-valerate
  • 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
  • Valrubicin
  • Valrubicina
  • Valrubicine
  • Valrubicinum
External IDs
AD 32 / AD-32 / NSC 246131 / NSC-246131
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ValstarSolution, concentrate40 mg/mLIntravesicalEndo Pharmaceuticals Solutions Inc.1998-10-01Not applicableUs
ValtaxinSolution40 mgIntravesicalEndo Pharmaceuticals Solutions Inc.2001-04-23Not applicableCanada
International/Other Brands
Valstar
Categories
UNII
2C6NUM6878
CAS number
56124-62-0
Weight
Average: 723.651
Monoisotopic: 723.213874712
Chemical Formula
C34H36F3NO13
InChI Key
ZOCKGBMQLCSHFP-KQRAQHLDSA-N
InChI
InChI=1S/C34H36F3NO13/c1-4-5-9-21(40)49-13-20(39)33(47)11-16-24(19(12-33)51-22-10-17(27(41)14(2)50-22)38-32(46)34(35,36)37)31(45)26-25(29(16)43)28(42)15-7-6-8-18(48-3)23(15)30(26)44/h6-8,14,17,19,22,27,41,43,45,47H,4-5,9-13H2,1-3H3,(H,38,46)/t14-,17-,19-,22-,27+,33-/m0/s1
IUPAC Name
2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(2,2,2-trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
SMILES
[H][[email protected]@]1(C[[email protected]@](O)(CC2=C(O)C3=C(C(O)=C12)C(=O)C1=C(OC)C=CC=C1C3=O)C(=O)COC(=O)CCCC)O[[email protected]]1C[[email protected]](NC(=O)C(F)(F)F)[[email protected]](O)[[email protected]](C)O1

Pharmacology

Indication

For the treatment of cancer of the bladder.

Structured Indications
Pharmacodynamics

Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.

Mechanism of action

Valrubicin is an anthracycline that affects a variety of inter-related biological functions, most of which involve nucleic acid metabolism. It readily penetrates into cells, where after DNA intercalation, it inhibits the incorporation of nucleosides into nucleic acids, causes extensive chromosomal damage, and arrests cell cycle in G2. Although valrubicin does not bind strongly to DNA, a principal mechanism of its action, mediated by valrubicin metabolites, is interference with the normal DNA breaking-resealing action of DNA topoisomerase II.

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

>99%

Metabolism

Valrubicin is metabolized to two primary metabolites: N-trifluoroacetyladriamycin and N-trifluoroacetyladriamycinol.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

The primary anticipated complications of overdosage associated with intravesical administration would be consistent with irritable bladder symptoms. Myelosuppression is possible if valrubicin is inadvertently administered systemically or if significant systemic exposure occurs following intravesical administration (e.g., in patients with bladder/rupture perforation). The maximum tolerated dose in humans by either intraperitoneal or intravenous administration is 600 mg/m2.

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

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
AcemetacinAcemetacin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Valrubicin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Valrubicin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
AlclofenacAlclofenac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumValrubicin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidValrubicin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Valrubicin can be decreased when it is combined with Amdinocillin.Withdrawn
AmoxicillinThe serum concentration of Valrubicin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Valrubicin.Approved, Investigational
AmpicillinThe serum concentration of Valrubicin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AndrographolideAndrographolide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
AnisodamineAnisodamine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
ApocyninApocynin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Valrubicin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumValrubicin may increase the respiratory depressant activities of Atracurium.Experimental
Atracurium besylateValrubicin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Valrubicin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Valrubicin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Valrubicin can be decreased when it is combined with Bacampicillin.Approved
BalsalazideBalsalazide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
BendazacBendazac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
BenoxaprofenBenoxaprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzylpenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Valrubicin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Valrubicin.Approved, Investigational
BevoniumBevonium may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Botulinum Toxin Type AValrubicin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BValrubicin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
BufexamacBufexamac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Valrubicin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Valrubicin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Valrubicin.Approved
Carbaspirin calciumCarbaspirin calcium may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
CarbenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Carbenicillin.Approved
Carbenicillin indanylThe serum concentration of Valrubicin can be decreased when it is combined with Carbenicillin indanyl.Approved
CarboplatinValrubicin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Valrubicin can be decreased when it is combined with Carfecillin.Experimental
CarprofenCarprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
CisatracuriumValrubicin may increase the respiratory depressant activities of Cisatracurium.Experimental
Cisatracurium besylateValrubicin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Valrubicin.Approved
Clodronic AcidValrubicin may increase the hypocalcemic activities of Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Valrubicin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethateValrubicin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Valrubicin can be decreased when it is combined with Cyclacillin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Valrubicin.Approved, Investigational
CyclosporineValrubicin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Valrubicin.Experimental
D-LimoneneD-Limonene may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
DecamethoniumValrubicin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Valrubicin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Valrubicin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
DiflunisalDiflunisal may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Valrubicin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Valrubicin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Valrubicin.Approved, Investigational
Domoic AcidValrubicin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chlorideValrubicin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
E-6201E-6201 may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Valrubicin can be decreased when it is combined with Epicillin.Experimental
EpirizoleEpirizole may decrease the excretion rate of Valrubicin 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 Valrubicin.Approved
EtanerceptEtanercept may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
EthenzamideEthenzamide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Etidronic acidValrubicin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
EtoricoxibEtoricoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
exisulindexisulind may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
FenbufenFenbufen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
FentiazacFentiazac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
FloctafenineFloctafenine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Valrubicin can be decreased when it is combined with Flucloxacillin.Approved
FlunixinFlunixin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
FlurbiprofenFlurbiprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Valrubicin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Valrubicin.Approved, Vet Approved
GallamineValrubicin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodideValrubicin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Valrubicin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
HigenamineHigenamine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
IbandronateValrubicin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
IndomethacinIndomethacin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Valrubicin.Experimental
LeflunomideLeflunomide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
LonazolacLonazolac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
LoxoprofenLoxoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
LumiracoxibLumiracoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Valrubicin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
MecamylamineValrubicin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
MetampicillinThe serum concentration of Valrubicin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Valrubicin can be decreased when it is combined with Meticillin.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Valrubicin.Experimental
MetocurineValrubicin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodideValrubicin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Valrubicin can be decreased when it is combined with Mezlocillin.Approved
MivacuriumValrubicin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
MofebutazoneMofebutazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
NafcillinThe serum concentration of Valrubicin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
NeosaxitoxinValrubicin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
NifenazoneNifenazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Niflumic AcidNiflumic Acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Valrubicin.Experimental
OlopatadineOlopatadine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Valrubicin which could result in a higher serum level.Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Valrubicin.Approved
OxacillinThe serum concentration of Valrubicin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Valrubicin.Approved, Vet Approved
PamidronateValrubicin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumValrubicin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
ParthenolideParthenolide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Valrubicin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Valrubicin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosidePeruvoside may decrease the cardiotoxic activities of Valrubicin.Experimental
PhenoxymethylpenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
PipecuroniumValrubicin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Valrubicin 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 Valrubicin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
PiroxicamPiroxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
PivampicillinThe serum concentration of Valrubicin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Valrubicin can be decreased when it is combined with Pivmecillinam.Approved
PranoprofenPranoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Procaine benzylpenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
PropicillinThe serum concentration of Valrubicin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Valrubicin.Experimental
PTC299PTC299 may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
PyrantelValrubicin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumValrubicin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental, Investigational
RisedronateValrubicin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumValrubicin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
SemapimodSemapimod may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
SRT501SRT501 may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
SuccinylcholineValrubicin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Valrubicin can be decreased when it is combined with Sulbactam.Approved
SulbenicillinThe serum concentration of Valrubicin can be decreased when it is combined with Sulbenicillin.Experimental
SulfasalazineSulfasalazine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Valrubicin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Valrubicin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
TazobactamThe serum concentration of Valrubicin can be decreased when it is combined with Tazobactam.Approved
Technetium Tc-99m etidronateValrubicin may increase the hypocalcemic activities of Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronateValrubicin may increase the hypocalcemic activities of Technetium Tc-99m medronate.Approved
TenidapTenidap may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Valrubicin can be increased when it is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Valrubicin can be decreased when it is combined with Ticarcillin.Approved, Vet Approved
Tiludronic acidValrubicin may increase the hypocalcemic activities of Tiludronic acid.Approved, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Valrubicin.Approved
TranilastTranilast may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Valrubicin.Approved, Investigational
TribenosideTribenoside may decrease the excretion rate of Valrubicin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational
TubocurarineValrubicin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Valrubicin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Valrubicin.Approved
VecuroniumValrubicin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
ZileutonZileuton may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidValrubicin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Valrubicin which could result in a higher serum level.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Francesca Scarpitta, Csilla Nemethne Racz, "Crystalline forms of valrubicin and processes for their preparation." U.S. Patent US20080139490, issued June 12, 2008.

US20080139490
General References
Not Available
External Links
ChemSpider
399974
ChEBI
135876
ChEMBL
CHEMBL1096885
Therapeutic Targets Database
DAP000650
PharmGKB
PA164748616
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Valrubicin
ATC Codes
L01DB09 — Valrubicin
FDA label
Download (80 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentTransitional Cell Carcinoma1
2CompletedTreatmentBladder Cancers2
2, 3CompletedTreatmentBladder Cancers / Carcinoma in Situ1
3TerminatedTreatmentCarcinoma in Situ / Non-muscle Invasive Bladder Cancer (NMIBC) / Transitional Cell Carcinoma1
3Unknown StatusTreatmentBladder Cancers1

Pharmacoeconomics

Manufacturers
  • Endo pharmaceutical solutions inc
Packagers
Dosage forms
FormRouteStrength
Solution, concentrateIntravesical40 mg/mL
SolutionIntravesical40 mg
Prices
Unit descriptionCostUnit
Valstar 40 mg/ml vial219.96USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116-117 °CNot Available
water solubilityinsolubleNot Available
logP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0325 mg/mLALOGPS
logP2.67ALOGPS
logP4.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area215.22 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity168.03 m3·mol-1ChemAxon
Polarizability69.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8596
Blood Brain Barrier-0.8907
Caco-2 permeable-0.6894
P-glycoprotein substrateSubstrate0.8165
P-glycoprotein inhibitor INon-inhibitor0.5747
P-glycoprotein inhibitor IINon-inhibitor0.5584
Renal organic cation transporterNon-inhibitor0.9348
CYP450 2C9 substrateNon-substrate0.8061
CYP450 2D6 substrateNon-substrate0.7947
CYP450 3A4 substrateSubstrate0.7203
CYP450 1A2 substrateNon-inhibitor0.7239
CYP450 2C9 inhibitorNon-inhibitor0.8228
CYP450 2D6 inhibitorNon-inhibitor0.9016
CYP450 2C19 inhibitorNon-inhibitor0.7565
CYP450 3A4 inhibitorNon-inhibitor0.6895
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7154
Ames testNon AMES toxic0.5421
CarcinogenicityNon-carcinogens0.9272
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.8652 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9846
hERG inhibition (predictor II)Inhibitor0.5129
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 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 / Anthraquinones / O-glycosyl compounds / Tetralins / Anisoles / Aryl ketones / Alkyl aryl ethers / Alpha-acyloxy ketones / Fatty acid esters / Oxanes
show 17 more
Substituents
Anthracycline / Anthracyclinone-skeleton / Tetracenequinone / 9,10-anthraquinone / 1,4-anthraquinone / Anthracene / Glycosyl compound / O-glycosyl compound / Tetralin / Aryl ketone
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

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. Brox L, Gowans B, Belch A: N-trifluoroacetyladriamycin-14-valerate and adriamycin induced DNA damage in the RPMI-6410 human lymphoblastoid cell line. Can J Biochem. 1980 Sep;58(9):720-5. [PubMed:7006761]
  2. Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. [PubMed:16019763]
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. [PubMed:16019763]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:36