U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11FN2O5
Molecular Weight 246.1924
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Floxuridine

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O

InChI

InChIKey=ODKNJVUHOIMIIZ-RRKCRQDMSA-N
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

HIDE SMILES / InChI

Molecular Formula C9H11FN2O5
Molecular Weight 246.1924
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/floxuridine.html

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. Floxuridine is used 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).Floxuridine first gained FDA approval in December 1970 under the brand name FUDR. The drug was initially marketed by Roche, which also did a lot of the initial work on 5-fluorouracil. The National Cancer Institute was an early developer of the drug. Roche sold its FUDR product line in 2001 to F H Faulding, which became Mayne Pharma.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.4 nM [IC50]
Target ID: CHEMBL614353
5.02 µM [IC50]
12.45 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FLOXURIDINE

Approved Use

Floxuridine for Injection, USP is effective in the 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.

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5547 ng/mL
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
79304 ng × h/mL
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.5 h
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1750 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 1750 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1750 mg/m2, 1 times / week
Sources:
unhealthy, 30-79
Health Status: unhealthy
Age Group: 30-79
Sex: M+F
Sources:
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 4, 50%)
Sources:
1650 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 1650 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1650 mg/m2, 1 times / week
Sources:
unhealthy, 30-79
Health Status: unhealthy
Age Group: 30-79
Sex: M+F
Sources:
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 3, 33.3%)
Sources:
544 mg/m2 5 times / day multiple, intraarterial
MTD
Dose: 544 mg/m2, 5 times / day
Route: intraarterial
Route: multiple
Dose: 544 mg/m2, 5 times / day
Sources:
unhealthy, 44-75
Health Status: unhealthy
Age Group: 44-75
Sex: M+F
Sources:
DLT: Mucositis...
Dose limiting toxicities:
Mucositis (grade 3-4, 72%)
Sources:
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Disc. AE: Fetal damage, Myocardial ischemia...
AEs leading to
discontinuation/dose reduction:
Fetal damage
Myocardial ischemia
Stomatitis
Esophagitis
Leukopenia
Vomiting
Diarrhea
Gastrointestinal ulcer
Gastrointestinal bleeding
Thrombocytopenia
Hemorrhage
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea grade 4, 50%
DLT, Disc. AE
1750 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 1750 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1750 mg/m2, 1 times / week
Sources:
unhealthy, 30-79
Health Status: unhealthy
Age Group: 30-79
Sex: M+F
Sources:
Diarrhea grade 3, 33.3%
DLT, Disc. AE
1650 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 1650 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1650 mg/m2, 1 times / week
Sources:
unhealthy, 30-79
Health Status: unhealthy
Age Group: 30-79
Sex: M+F
Sources:
Mucositis grade 3-4, 72%
DLT
544 mg/m2 5 times / day multiple, intraarterial
MTD
Dose: 544 mg/m2, 5 times / day
Route: intraarterial
Route: multiple
Dose: 544 mg/m2, 5 times / day
Sources:
unhealthy, 44-75
Health Status: unhealthy
Age Group: 44-75
Sex: M+F
Sources:
Diarrhea Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Esophagitis Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Fetal damage Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Gastrointestinal bleeding Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Gastrointestinal ulcer Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Hemorrhage Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Leukopenia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Myocardial ischemia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Stomatitis Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Thrombocytopenia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Vomiting Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
Surgery as adjuvant therapy? The treatment of peritoneal metastases from gastrointestinal malignancy.
2001 Dec
Coupling of 5-fluoro 2'-deoxyuridine to lactosaminated poly-l-lysine: an approach to a regional, non-invasive chemotherapy of liver micrometastases.
2001 Feb 15
The significance of thymidine phosphorylase expression in colorectal cancer.
2001 Jan-Feb
Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses.
2001 Jul 1
Role of Bax in apoptosis of IL-3-dependent cells.
2001 Jul 27
Role of the human concentrative nucleoside transporter (hCNT1) in the cytotoxic action of 5[Prime]-deoxy-5-fluorouridine, an active intermediate metabolite of capecitabine, a novel oral anticancer drug.
2001 Jun
Locoregional therapy for liver metastases from colorectal cancer: the possibilities of intraarterial chemotherapy, and new hepatic-directed modalities.
2001 Mar-Apr
Effects of concomitant use of doxifluridine, radiotherapy and immunotherapy in patients with advanced cervical cancer.
2001 Mar-Apr
Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA.
2001 May 1
[Hepatic infusion of docetaxel using PEIT for a patient with stage IV breast cancer].
2001 Nov
Thymidine phosphorylase expression is useful in selecting adjuvant chemotherapy for stage III gastric cancer.
2001 Oct
Inhibition of thymidylate synthase activity by antisense oligodeoxynucleotide and possible role in thymineless treatment.
2001 Sep
Extrahepatic biliary stenoses after hepatic arterial infusion (HAI) of floxuridine (FUdR) for liver metastases from colorectal cancer.
2001 Sep-Oct
Intrahepatic arterial infusion of chemotherapy: clinical results.
2002 Apr
Impact of the oxaliplatin-5 fluorouracil-folinic acid combination on respective intracellular determinants of drug activity.
2002 Apr 8
[A case of long surviving advanced recurrent breast cancer with multiple bone metastases responding to treatment with 5'-DFUR combined with MPA].
2002 Feb
A controlled "before-after" study: impact of a clinical guidelines programme and regional cancer network organization on medical practice.
2002 Feb 1
[Antimetastatic and antitumor effects of fluoropyrimidines alone and combined with taxanes in a murine model of breast cancer metastatic to the lung].
2002 Jan
A phase II study of doxifluridine in elderly patients with advanced gastric cancer: the Japan Clinical Oncology Group Study (JCOG 9410).
2002 Mar
Combined-modality treatment for resectable metastatic colorectal carcinoma to the liver: surgical resection of hepatic metastases in combination with continuous infusion of chemotherapy--an intergroup study.
2002 Mar 15
Neoadjuvant chemotherapy with CPT-11 and cisplatin downstages locally advanced gastric cancer.
2002 Mar-Apr
Treatment of patients with superficial bladder cancer by intravesical instillation of anticancer drugs plus oral chemotherapy following TUR-Bt: a randomized controlled trial.
2002 Mar-Apr
Conjugates of nucleoside analogs with lactosaminated human albumin to selectively increase the drug levels in liver blood: requirements for a regional chemotherapy.
2002 May
Schedule-selective biochemical modulation of 5-fluorouracil in advanced colorectal cancer--a phase II study.
2002 May 2
Patents

Sample Use Guides

Usual Adult Dose for Liver Metastasis in Adenocarcinoma Recommended dose: 0.1 to 0.6 mg/kg/day by continuous arterial infusion; the higher dosage ranges (0.4 mg to 0.6 mg) are usually used for hepatic artery infusion
Route of Administration: Intra-arterial
Coincubation of [3H]-FAU in vitro with 50 nmol/L Floxuridine decreased FAU incorporation into DNA by 70% in HT29 and 84% in LS174T cells
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:54:57 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:57 GMT 2025
Record UNII
039LU44I5M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FUDR
Preferred Name English
Floxuridine
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FLOXURIDINE [USP IMPURITY]
Common Name English
5-FLUORO-2'-DEOXYURIDINE
Systematic Name English
5-FUDR
Common Name English
FLOXURIDINE [USP MONOGRAPH]
Common Name English
FLOXURIDINE [ORANGE BOOK]
Common Name English
NSC-27640
Code English
FLOXURIDINE [USP-RS]
Common Name English
FLOXURIDINE [MART.]
Common Name English
FLOXURIDINE [MI]
Common Name English
floxuridine [INN]
Common Name English
FLOXURIDINE [VANDF]
Common Name English
FLOXURIDINE [HSDB]
Common Name English
FLOXURIDINE [USAN]
Common Name English
URIDINE, 2'-DEOXY-5-FLUORO-
Systematic Name English
FLUORODEOXYURIDINE
Systematic Name English
2'-DEOXY-5-FLUOROURIDINE
Systematic Name English
Floxuridine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC L01BC09
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
LIVERTOX NBK548421
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000180853
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
FDA ORPHAN DRUG 195104
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
NDF-RT N0000007770
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
Code System Code Type Description
MERCK INDEX
m5414
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY Merck Index
FDA UNII
039LU44I5M
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
CAS
50-91-9
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
SMS_ID
100000081003
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
MESH
D005467
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
CHEBI
60761
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
PUBCHEM
5790
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
WIKIPEDIA
FLOXURIDINE
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-072-5
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
IUPHAR
4801
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
DAILYMED
039LU44I5M
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
DRUG CENTRAL
1184
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
DRUG BANK
DB00322
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
RS_ITEM_NUM
1271008
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
INN
2010
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023057
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
NCI_THESAURUS
C504
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
HSDB
3227
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
ChEMBL
CHEMBL917
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
RXCUI
4488
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY RxNorm
NSC
27640
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
EVMPD
SUB07659MIG
Created by admin on Mon Mar 31 17:54:57 GMT 2025 , Edited by admin on Mon Mar 31 17:54:57 GMT 2025
PRIMARY
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