Identification

Name
Floxuridine
Accession Number
DB00322  (APRD00692)
Type
Small Molecule
Groups
Approved
Description

An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection. Floxuridine is available as a sterile, nonpyrogenic, lyophilized powder for reconstitution. When administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. [PubChem]

Structure
Thumb
Synonyms
  • 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil
  • 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 2'-Deoxy-5-fluorouridine
  • 5-Fluoro-2-desoxyuridine
  • 5-Fluorodeoxyuridine
  • 5-Fluorouracil 2'-deoxyriboside
  • 5-Fluorouracil deoxyriboside
  • 5FDU
  • beta-5-Fluoro-2'-deoxyuridine
  • Deoxyfluorouridine
  • FdU
  • Floxiridina
  • Floxuridin
  • Floxuridine
  • Floxuridinum
  • Fluorodeoxyuridine
  • Fluoruridine Deoxyribose
External IDs
NSC-27640
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FloxuridineInjection, powder, lyophilized, for solution500 mg/5mLIntra-arterialFresenius Kabi2001-03-15Not applicableUs
International/Other Brands
FUDR (Mayne)
Categories
UNII
039LU44I5M
CAS number
50-91-9
Weight
Average: 246.1924
Monoisotopic: 246.065199677
Chemical Formula
C9H11FN2O5
InChI Key
ODKNJVUHOIMIIZ-RRKCRQDMSA-N
InChI
InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
IUPAC Name
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES

Pharmacology

Indication

For palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. Also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion).

Structured Indications
Pharmacodynamics

Floxuridine is a pyrimidine analog that acts as an inhibitor of the S-phase of cell division. This selectively kills rapidly dividing cells. Floxuridine is an anti-metabolite. Anti-metabolites masquerade as pyramidine-like molecules which prevents normal pyrimidines from being incorporated into DNA during the S phase of the cell cycle. Flurouracil (the end-product of catabolism of floxuridine) blocks an enzyme which converts cytosine nucleosides into the deoxy derivative. In addition, DNA synthesis is further inhibited because fluoruracil blocks the incorporation of the thymdine nucleotide into the DNA strand.

Mechanism of action

Floxuridine is rapidly catabolized to 5-fluorouracil, which is the active form of the drug. The primary effect is interference with DNA synthesis and to a lesser extent, inhibition of RNA formation through the drug's incorporation into RNA, thus leading to the production of fraudulent RNA. Fluorouracil also inhibits uracil riboside phophorylase, which prevents the utilization of preformed uracil in RNA synthesis. As well, the monophosphate of floxuridine, 5-fluoro-2'-deoxyuridine-5'-phosphate (FUDR-MP) inhibits the enzyme thymidylate synthetase. This leads to the inhibition of methylation of deoxyuridylic acid to thymidylic acid, thus interfering with DNA synthesis.

TargetActionsOrganism
AThymidylate synthaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination

The drug is excreted intact and as urea, fluorouracil, a-fluoro-bureidopropionic acid, dihydrofluorouracil, a-fluoro-b-guanidopropionic acid and a-fluoro-b-alanine in the urine; it is also expired as respiratory carbon dioxide.

Half life
Not Available
Clearance
Not Available
Toxicity

Oral, rat LD50: 215 mg/kg. Signs of overdose include nausea, vomiting, diarrhea, gastrointestinal ulceration and bleeding, and bone marrow depression (including thrombocytopenia, leukopenia and agranulocytosis).

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

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacThe metabolism of Aceclofenac can be decreased when combined with Floxuridine.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Floxuridine.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Floxuridine.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Floxuridine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Floxuridine.Experimental
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Floxuridine.Approved, Vet Approved
AlosetronThe metabolism of Alosetron can be decreased when combined with Floxuridine.Approved, Withdrawn
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Floxuridine.Approved, Illicit, Investigational
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Floxuridine.Approved, Withdrawn
AmiodaroneThe metabolism of Amiodarone can be decreased when combined with Floxuridine.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Floxuridine.Approved
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Floxuridine.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Floxuridine.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Floxuridine.Approved
Arachidonic AcidThe metabolism of Arachidonic Acid can be decreased when combined with Floxuridine.Experimental
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Floxuridine.Approved, Investigational
ArtemetherThe metabolism of Artemether can be decreased when combined with Floxuridine.Approved
AtazanavirThe metabolism of Atazanavir can be decreased when combined with Floxuridine.Approved, Investigational
AzelastineThe metabolism of Azelastine can be decreased when combined with Floxuridine.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Floxuridine.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Floxuridine.Approved, Investigational
BexaroteneThe metabolism of Bexarotene can be decreased when combined with Floxuridine.Approved, Investigational
BortezomibThe metabolism of Bortezomib can be decreased when combined with Floxuridine.Approved, Investigational
BosentanThe serum concentration of Bosentan can be increased when it is combined with Floxuridine.Approved, Investigational
BrivaracetamThe metabolism of Brivaracetam can be decreased when combined with Floxuridine.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Floxuridine.Approved
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Floxuridine.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Bupropion can be decreased when combined with Floxuridine.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Floxuridine.Approved
CabozantinibThe metabolism of Cabozantinib can be decreased when combined with Floxuridine.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Floxuridine.Approved
CandesartanThe metabolism of Candesartan can be decreased when combined with Floxuridine.Approved
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Floxuridine.Approved
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Floxuridine.Approved, Investigational
CelecoxibThe metabolism of Celecoxib can be decreased when combined with Floxuridine.Approved, Investigational
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Floxuridine.Approved
CimetidineThe serum concentration of the active metabolites of Floxuridine can be increased when Floxuridine is used in combination with Cimetidine.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Floxuridine.Approved
CisaprideThe metabolism of Cisapride can be decreased when combined with Floxuridine.Approved, Investigational, Withdrawn
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Floxuridine.Approved, Nutraceutical
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Floxuridine.Approved
ClozapineThe risk or severity of adverse effects can be increased when Floxuridine is combined with Clozapine.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Floxuridine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Floxuridine.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Floxuridine.Experimental
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Floxuridine.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Floxuridine.Approved, Investigational
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Floxuridine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Floxuridine.Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Floxuridine.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Floxuridine.Approved, Illicit, Vet Approved
DiclofenacThe serum concentration of Diclofenac can be increased when it is combined with Floxuridine.Approved, Vet Approved
DicoumarolThe metabolism of Dicoumarol can be decreased when combined with Floxuridine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Floxuridine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Floxuridine.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Floxuridine.Approved
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Floxuridine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Floxuridine.Approved, Investigational
DoconexentThe metabolism of Doconexent can be decreased when combined with Floxuridine.Investigational
DolasetronThe metabolism of Dolasetron can be decreased when combined with Floxuridine.Approved
DonepezilThe metabolism of Donepezil can be decreased when combined with Floxuridine.Approved
DopamineThe metabolism of Dopamine can be decreased when combined with Floxuridine.Approved
DorzolamideThe metabolism of Dorzolamide can be decreased when combined with Floxuridine.Approved
DoxepinThe metabolism of Doxepin can be decreased when combined with Floxuridine.Approved
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Floxuridine.Approved, Illicit
EletriptanThe metabolism of Eletriptan can be decreased when combined with Floxuridine.Approved, Investigational
EnasidenibThe metabolism of Enasidenib can be decreased when combined with Floxuridine.Approved
EpoprostenolThe metabolism of Epoprostenol can be decreased when combined with Floxuridine.Approved
EstradiolThe metabolism of Estradiol can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
EstroneThe metabolism of Estrone can be decreased when combined with Floxuridine.Approved
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Floxuridine.Approved
EtodolacThe metabolism of Etodolac can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Floxuridine.Approved, Investigational
EtravirineThe metabolism of Etravirine can be decreased when combined with Floxuridine.Approved
FingolimodFloxuridine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Floxuridine.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Floxuridine.Approved, Illicit
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Floxuridine.Approved, Vet Approved
FlurbiprofenThe metabolism of Flurbiprofen can be decreased when combined with Floxuridine.Approved, Investigational
FluvastatinThe metabolism of Fluvastatin can be decreased when combined with Floxuridine.Approved
FormoterolThe metabolism of Formoterol can be decreased when combined with Floxuridine.Approved, Investigational
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Floxuridine.Approved
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Floxuridine.Investigational
GavestinelThe metabolism of Gavestinel can be decreased when combined with Floxuridine.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Floxuridine.Investigational
GimeracilThe serum concentration of the active metabolites of Floxuridine can be increased when Floxuridine is used in combination with Gimeracil.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Floxuridine.Experimental
GliclazideThe metabolism of Gliclazide can be decreased when combined with Floxuridine.Approved
GlimepirideThe metabolism of Glimepiride can be decreased when combined with Floxuridine.Approved
GlipizideThe metabolism of Glipizide can be decreased when combined with Floxuridine.Approved
GlyburideThe metabolism of Glyburide can be decreased when combined with Floxuridine.Approved
GuanfacineThe metabolism of Guanfacine can be decreased when combined with Floxuridine.Approved, Investigational
HaloperidolThe metabolism of Haloperidol can be decreased when combined with Floxuridine.Approved
HalothaneThe metabolism of Halothane can be decreased when combined with Floxuridine.Approved, Vet Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Floxuridine.Approved
HistamineThe metabolism of Histamine can be decreased when combined with Floxuridine.Approved, Investigational
HydromorphoneThe metabolism of Hydromorphone can be decreased when combined with Floxuridine.Approved, Illicit
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Floxuridine.Approved
IdarubicinThe metabolism of Idarubicin can be decreased when combined with Floxuridine.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Floxuridine.Approved
ImatinibThe metabolism of Imatinib can be decreased when combined with Floxuridine.Approved
indisulamThe metabolism of indisulam can be decreased when combined with Floxuridine.Investigational
IndomethacinThe metabolism of Indomethacin can be decreased when combined with Floxuridine.Approved, Investigational
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Floxuridine.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Floxuridine.Investigational
IrbesartanThe metabolism of Irbesartan can be decreased when combined with Floxuridine.Approved, Investigational
IxazomibThe metabolism of Ixazomib can be decreased when combined with Floxuridine.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Floxuridine.Approved, Vet Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Floxuridine.Approved
KetoprofenThe metabolism of Ketoprofen can be decreased when combined with Floxuridine.Approved, Vet Approved
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Floxuridine.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Floxuridine.Experimental
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Floxuridine.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Floxuridine is combined with Leflunomide.Approved, Investigational
LesinuradThe metabolism of Lesinurad can be decreased when combined with Floxuridine.Approved
LicofeloneThe metabolism of Licofelone can be decreased when combined with Floxuridine.Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Floxuridine.Approved, Vet Approved
LoratadineThe metabolism of Loratadine can be decreased when combined with Floxuridine.Approved
LornoxicamThe metabolism of Lornoxicam can be decreased when combined with Floxuridine.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Floxuridine.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Floxuridine.Approved, Investigational
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Floxuridine.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Floxuridine.Approved, Nutraceutical, Vet Approved
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Floxuridine.Approved, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Floxuridine.Investigational, Withdrawn
MestranolThe metabolism of Mestranol can be decreased when combined with Floxuridine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Floxuridine.Withdrawn
MethadoneThe metabolism of Methadone can be decreased when combined with Floxuridine.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Floxuridine.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Floxuridine.Experimental
MetronidazoleThe metabolism of Metronidazole can be decreased when combined with Floxuridine.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Floxuridine.Approved
MoclobemideThe metabolism of Moclobemide can be decreased when combined with Floxuridine.Approved
MontelukastThe metabolism of Montelukast can be decreased when combined with Floxuridine.Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Floxuridine.Approved, Vet Approved
NatalizumabThe risk or severity of adverse effects can be increased when Floxuridine is combined with Natalizumab.Approved, Investigational
NateglinideThe metabolism of Nateglinide can be decreased when combined with Floxuridine.Approved, Investigational
NetupitantThe metabolism of Netupitant can be decreased when combined with Floxuridine.Approved
NevirapineThe metabolism of Nevirapine can be decreased when combined with Floxuridine.Approved
NiclosamideThe metabolism of Niclosamide can be decreased when combined with Floxuridine.Approved, Vet Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Floxuridine.Approved
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Floxuridine.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Floxuridine.Experimental
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Floxuridine.Approved
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Floxuridine.Approved
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Floxuridine.Approved
OuabainOuabain may decrease the cardiotoxic activities of Floxuridine.Approved
OxaprozinThe metabolism of Oxaprozin can be decreased when combined with Floxuridine.Approved
PaclitaxelThe metabolism of Paclitaxel can be decreased when combined with Floxuridine.Approved, Vet Approved
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Floxuridine.Approved
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Floxuridine.Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Floxuridine.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Floxuridine.Experimental
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Floxuridine.Withdrawn
PhenobarbitalThe metabolism of Phenobarbital can be decreased when combined with Floxuridine.Approved
PhenprocoumonThe metabolism of Phenprocoumon can be decreased when combined with Floxuridine.Approved
PhenylbutazoneThe metabolism of Phenylbutazone can be decreased when combined with Floxuridine.Approved, Vet Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Floxuridine.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Floxuridine.Approved, Investigational
PioglitazoneThe metabolism of Pioglitazone can be decreased when combined with Floxuridine.Approved, Investigational
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Floxuridine.Approved, Investigational
PitavastatinThe metabolism of Pitavastatin can be decreased when combined with Floxuridine.Approved
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Floxuridine.Approved
PravastatinThe metabolism of Pravastatin can be decreased when combined with Floxuridine.Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Floxuridine.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Floxuridine.Approved
PromazineThe metabolism of Promazine can be decreased when combined with Floxuridine.Approved, Vet Approved
PropofolThe metabolism of Propofol can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Floxuridine.Experimental
QuazepamThe metabolism of Quazepam can be decreased when combined with Floxuridine.Approved, Illicit
QuinidineThe metabolism of Quinidine can be decreased when combined with Floxuridine.Approved
QuinineThe metabolism of Quinine can be decreased when combined with Floxuridine.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Floxuridine is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Floxuridine.Approved
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Floxuridine.Approved, Investigational
RifampicinThe metabolism of Rifampicin can be decreased when combined with Floxuridine.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Floxuridine.Investigational
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Floxuridine.Investigational, Withdrawn
RoflumilastRoflumilast may increase the immunosuppressive activities of Floxuridine.Approved
RosiglitazoneThe metabolism of Rosiglitazone can be decreased when combined with Floxuridine.Approved, Investigational
RosuvastatinThe metabolism of Rosuvastatin can be decreased when combined with Floxuridine.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Floxuridine.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Floxuridine.Approved
RupatadineThe metabolism of Rupatadine can be decreased when combined with Floxuridine.Approved
Salicylic acidThe metabolism of Salicylic acid can be decreased when combined with Floxuridine.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Floxuridine.Approved
SertralineThe metabolism of Sertraline can be decreased when combined with Floxuridine.Approved
SildenafilThe metabolism of Sildenafil can be decreased when combined with Floxuridine.Approved, Investigational
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Floxuridine.Approved
SitaxentanThe metabolism of Sitaxentan can be decreased when combined with Floxuridine.Approved, Investigational, Withdrawn
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Floxuridine.Investigational
SulfadiazineThe metabolism of Sulfadiazine can be decreased when combined with Floxuridine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Sulfamethoxazole can be decreased when combined with Floxuridine.Approved
SulfamoxoleThe metabolism of Sulfamoxole can be decreased when combined with Floxuridine.Approved
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Floxuridine.Approved
SulfisoxazoleThe metabolism of Sulfisoxazole can be decreased when combined with Floxuridine.Approved, Vet Approved
SuprofenThe metabolism of Suprofen can be decreased when combined with Floxuridine.Approved, Withdrawn
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Floxuridine.Approved, Investigational
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Floxuridine.Approved
TapentadolThe metabolism of Tapentadol can be decreased when combined with Floxuridine.Approved
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Floxuridine.Investigational
TemazepamThe metabolism of Temazepam can be decreased when combined with Floxuridine.Approved
TenoxicamThe metabolism of Tenoxicam can be decreased when combined with Floxuridine.Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Floxuridine.Approved, Investigational, Vet Approved
TerfenadineThe metabolism of Terfenadine can be decreased when combined with Floxuridine.Withdrawn
TestosteroneThe metabolism of Testosterone can be decreased when combined with Floxuridine.Approved, Investigational
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Floxuridine.Investigational
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Floxuridine.Approved, Investigational, Withdrawn
TheophyllineThe metabolism of Theophylline can be decreased when combined with Floxuridine.Approved
ThiamylalThe metabolism of Thiamylal can be decreased when combined with Floxuridine.Approved, Vet Approved
TofacitinibFloxuridine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolbutamideThe metabolism of Tolbutamide can be decreased when combined with Floxuridine.Approved
TolterodineThe metabolism of Tolterodine can be decreased when combined with Floxuridine.Approved, Investigational
TorasemideThe metabolism of Torasemide can be decreased when combined with Floxuridine.Approved
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Floxuridine.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Floxuridine.Approved, Investigational
TreprostinilThe metabolism of Treprostinil can be decreased when combined with Floxuridine.Approved, Investigational
TretinoinThe metabolism of Tretinoin can be decreased when combined with Floxuridine.Approved, Investigational, Nutraceutical
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Floxuridine.Approved
TrimethoprimThe metabolism of Trimethoprim can be decreased when combined with Floxuridine.Approved, Vet Approved
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Floxuridine.Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Floxuridine.Withdrawn
ValdecoxibThe metabolism of Valdecoxib can be decreased when combined with Floxuridine.Investigational, Withdrawn
Valproic AcidThe metabolism of Valproic Acid can be decreased when combined with Floxuridine.Approved, Investigational
ValsartanThe metabolism of Valsartan can be decreased when combined with Floxuridine.Approved, Investigational
VenlafaxineThe metabolism of Venlafaxine can be decreased when combined with Floxuridine.Approved
VerapamilThe metabolism of Verapamil can be decreased when combined with Floxuridine.Approved
VicrivirocThe metabolism of Vicriviroc can be decreased when combined with Floxuridine.Investigational
VismodegibThe metabolism of Vismodegib can be decreased when combined with Floxuridine.Approved
VoriconazoleThe metabolism of Voriconazole can be decreased when combined with Floxuridine.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Floxuridine.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Floxuridine.Approved
XimelagatranThe metabolism of Ximelagatran can be decreased when combined with Floxuridine.Approved, Investigational, Withdrawn
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Floxuridine.Approved
ZafirlukastThe metabolism of Zafirlukast can be decreased when combined with Floxuridine.Approved, Investigational
ZalcitabineThe metabolism of Zalcitabine can be decreased when combined with Floxuridine.Approved
ZaltoprofenThe metabolism of Zaltoprofen can be decreased when combined with Floxuridine.Approved
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Floxuridine.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Floxuridine.Approved, Investigational, Withdrawn
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Floxuridine.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Floxuridine.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Floxuridine.Approved
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,041,335.

General References
Not Available
External Links
Human Metabolome Database
HMDB14467
KEGG Drug
D04197
KEGG Compound
C11736
PubChem Compound
5790
PubChem Substance
46508645
ChemSpider
5586
BindingDB
50340678
ChEBI
60761
ChEMBL
CHEMBL917
Therapeutic Targets Database
DAP001245
PharmGKB
PA449652
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Floxuridine
MSDS
Download (40.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentCholangiocellular Carcinoma) (ICC) / Cholangiolar Carcinoma / Intrahepatic Cholangiocarcinoma / Peripheral Cholangiocarcinoma1
1Active Not RecruitingTreatmentColorectal Cancers / Metastatic Cancers1
1Active Not RecruitingTreatmentMalignant Neoplasm of Colon / Rectal Carcinoma1
1CompletedTreatmentCancers1
1CompletedTreatmentColorectal Cancers / Metastatic Cancers1
1CompletedTreatmentNeoplasms1
1CompletedTreatmentNeoplasms Metastasis / Neoplasms, Colorectal / Neoplasms, Hepatic1
1RecruitingTreatmentCholangiocarcinomas / Neoplasms, Hepatic1
1RecruitingTreatmentStage IV Fallopian Tube Cancer / Stage IV Ovarian Cancer / Stage IV Primary Peritoneal Cancer1
1, 2Active Not RecruitingTreatmentHepatic Metastases / Recurrent Colon Cancer / Recurrent Rectal Cancer / Stage IV Colon Cancer / Stage IV Rectal Cancer1
2Active Not RecruitingTreatmentColorectal Cancers / Metastatic Cancers1
2Active Not RecruitingTreatmentLiver Cancer1
2CompletedTreatmentAdenocarcinoma of the Colon / Adenocarcinoma of the Rectum / Hepatic Metastases / Recurrent Colon Cancer / Recurrent Rectal Cancer / Stage IV Colon Cancer / Stage IV Rectal Cancer1
2CompletedTreatmentCancer, Ovarian / Carcinoid tumour of the gastrointestinal tract / Colorectal Cancers / Gastrointestinal Stromal Tumors / Malignant Neoplasm of Stomach / Peritoneal Cavity Cancer / Small Intestine Cancer1
2CompletedTreatmentColorectal Cancers / Metastatic Cancers4
2CompletedTreatmentEsophageal Cancers1
2CompletedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
2CompletedTreatmentGastric Adenocarcinoma / Malignant Neoplasm of Stomach1
2CompletedTreatmentHepatic Metastases / Recurrent Colon Cancer / Recurrent Rectal Cancer / Stage IV Colon Cancer / Stage IV Rectal Cancer1
2CompletedTreatmentHepatic neoplasms malignant1
2CompletedTreatmentMalignant Neoplasm of Stomach3
2RecruitingTreatmentCholangiocellular Carcinoma / Cholangiolar Carcinoma / Intrahepatic Cholangiocarcinoma / Peripheral Cholangiocarcinoma1
2RecruitingTreatmentColorectal Adenocarcinoma Metastatic to the Liver1
2TerminatedTreatmentColorectal Cancers1
2TerminatedTreatmentEsophageal Cancers / Gastric Adenocarcinoma / Malignant Neoplasm of Stomach1
2TerminatedTreatmentMalignant Neoplasm of Stomach1
2Unknown StatusTreatmentColorectal Cancers / Metastatic Cancers1
3CompletedTreatmentColorectal Cancers / Metastatic Cancers2
3RecruitingTreatmentColorectal Cancers / Metastasis1
3RecruitingTreatmentMetastatic Colorectal Cancers1
3TerminatedTreatmentColorectal Cancers / Metastatic Cancers1

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntra-arterial500 mg/5mL
Prices
Unit descriptionCostUnit
Floxuridine 500 mg vial144.0USD vial
Fudr 500 mg vial121.06USD vial
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)150.5 °CPhysProp
water solubility1.19E+004 mg/LNot Available
logP-1.16HANSCH,C ET AL. (1995)
pKa7.44SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility40.8 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.26 m3·mol-1ChemAxon
Polarizability20.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9589
Blood Brain Barrier+0.768
Caco-2 permeable-0.8988
P-glycoprotein substrateNon-substrate0.7043
P-glycoprotein inhibitor INon-inhibitor0.854
P-glycoprotein inhibitor IINon-inhibitor0.888
Renal organic cation transporterNon-inhibitor0.8956
CYP450 2C9 substrateNon-substrate0.805
CYP450 2D6 substrateNon-substrate0.8668
CYP450 3A4 substrateNon-substrate0.5459
CYP450 1A2 substrateNon-inhibitor0.9125
CYP450 2C9 inhibitorNon-inhibitor0.9159
CYP450 2D6 inhibitorNon-inhibitor0.9235
CYP450 2C19 inhibitorNon-inhibitor0.9162
CYP450 3A4 inhibitorNon-inhibitor0.8926
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8378
Ames testNon AMES toxic0.6041
CarcinogenicityNon-carcinogens0.7542
BiodegradationNot ready biodegradable0.9528
Rat acute toxicity2.5247 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9508
hERG inhibition (predictor II)Non-inhibitor0.7771
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.43 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00lr-9600000000-155a97133c7827d2a1ce
GC-MS Spectrum - CI-BGC-MSsplash10-001i-3900000000-44f00976f508bab47f36
GC-MS Spectrum - CI-BGC-MSsplash10-00kb-2910000000-2efae68e874a5fdba01c
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 pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2'-deoxyribonucleosides
Direct Parent
Pyrimidine 2'-deoxyribonucleosides
Alternative Parents
Pyrimidones / Halopyrimidines / Hydroxypyrimidines / Aryl fluorides / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds
show 6 more
Substituents
Pyrimidine 2'-deoxyribonucleoside / Halopyrimidine / Hydroxypyrimidine / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Pyrimidine / Heteroaromatic compound / Tetrahydrofuran
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, nucleoside analogue, pyrimidine 2'-deoxyribonucleoside (CHEBI:60761)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Thymidylate synthase activity
Specific Function
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name
TYMS
Uniprot ID
P04818
Uniprot Name
Thymidylate synthase
Molecular Weight
35715.65 Da
References
  1. Ferguson PJ, Collins O, Dean NM, DeMoor J, Li CS, Vincent MD, Koropatnick J: Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86. [PubMed:10482907]
  2. Kubota T: [Theoretical basis for low-dose CDDP/5-FU therapy]. Gan To Kagaku Ryoho. 1999 Oct;26(11):1536-41. [PubMed:10553409]
  3. Kuwa K, Sakamoto S, Sassa S, Yoshimura S, Maemura M, Nakayama T: Effects of long-term administration of UFT plus leucovorin on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5139-42. [PubMed:10697523]
  4. Kuwa K, Sakamoto S, Mitamura T, Kudo H, Suzuki S, Fukushima M: Effects of a low dose leucovorin with 5-fluorouracil derivative on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5143-8. [PubMed:10697524]
  5. Murakami Y, Kazuno H, Emura T, Tsujimoto H, Suzuki N, Fukushima M: Different mechanisms of acquired resistance to fluorinated pyrimidines in human colorectal cancer cells. Int J Oncol. 2000 Aug;17(2):277-83. [PubMed:10891536]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transferase activity, transferring pentosyl groups
Specific Function
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in v...
Gene Name
TYMP
Uniprot ID
P19971
Uniprot Name
Thymidine phosphorylase
Molecular Weight
49954.965 Da
References
  1. BIRNIE GD, KROEGER H, HEIDELBERGER C: STUDIES OF FLUORINATED PYRIMIDINES. XVIII. THE DEGRADATION OF 5-FLUORO-2'-DEOXYURIDINE AND RELATED COMPOUNDS BY NUCLEOSIDE PHOSPHORYLASE. Biochemistry. 1963 May-Jun;2:566-72. [PubMed:14069549]
  2. Tsume Y, Hilfinger JM, Amidon GL: Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: increased transporter affinity and metabolic stability. Mol Pharm. 2008 Sep-Oct;5(5):717-27. doi: 10.1021/mp800008c. Epub 2008 Jul 25. [PubMed:18652477]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:35