floxuridine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
uridine derivatives used as antiviral agents and as antineoplastics 1184 50-91-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • floxuridine
  • floxuridin
  • 5-Fluorouracil deoxyriboside
  • 5-Fluorodeoxyuridine
An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; 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.
  • Molecular weight: 246.19
  • Formula: C9H11FN2O5
  • CLOGP: -1.40
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 99.10
  • ALOGS: -0.78
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 18, 1970 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01BC09 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
FDA CS M0006020 Deoxyuridine
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D009676 Noxae
FDA EPC N0000180853 Antimetabolite
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:132992 radiosensitizers

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Malignant neoplasm of liver indication 93870000 DOID:3571
Primary malignant neoplasm of gastrointestinal tract indication 363745004
Nutritional disorder contraindication 2492009 DOID:374
Acute hemorrhage contraindication 8573003
Hyperbilirubinemia contraindication 14783006 DOID:2741
Esophagitis contraindication 16761005 DOID:11963
Gastrointestinal ulcer contraindication 40845000
Fibrosis of bile duct contraindication 48124008
Stomatitis contraindication 61170000 DOID:9637
Acute infectious disease contraindication 63171007
Gastrointestinal hemorrhage contraindication 74474003
Cholecystitis contraindication 76581006 DOID:1949
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Persistent vomiting contraindication 196746003
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Pharyngitis contraindication 405737000 DOID:2275
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.98 acidic
pKa2 13.02 acidic
pKa3 13.7 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidylate synthase Enzyme INHIBITOR DRUGBANK CHEMBL
Thymidylate synthase Enzyme IC50 9.40 CHEMBL

External reference:

IDSource
4017811 VUID
N0000146171 NUI
D04197 KEGG_DRUG
4017811 VANDF
C0016343 UMLSCUI
CHEBI:60761 CHEBI
5790 PUBCHEM_CID
CHEMBL917 ChEMBL_ID
DB00322 DRUGBANK_ID
D005467 MESH_DESCRIPTOR_UI
4801 IUPHAR_LIGAND_ID
2010 INN_ID
039LU44I5M UNII
4488 RXNORM
40527 MMSL
4731 MMSL
d01344 MMSL
002648 NDDF
387432008 SNOMEDCT_US
75927008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Floxuridine HUMAN PRESCRIPTION DRUG LABEL 1 0143-9270 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRA-ARTERIAL ANDA 24 sections
Floxuridine HUMAN PRESCRIPTION DRUG LABEL 1 63323-145 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRA-ARTERIAL ANDA 13 sections