U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11FN2O5
Molecular Weight 246.1928
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLOXURIDINE

SMILES

C1[C@@]([H])([C@@]([H])(CO)O[C@@]1([H])n2cc(c(nc2=O)O)F)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 246.1928
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

TargetsConditions

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

954892800000
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
Bone morphogenetic protein-2, but not bone morphogenetic protein-7, promotes dendritic growth and calbindin phenotype in cultured rat striatal neurons.
2001
5'-deoxy-5-fluorouridine, medroxyprogestrone acetate and mitoxantrone hydrochloride for advanced or recurrent breast cancer.
2001
Impact of thymidine phosphorylase surexpression on fluoropyrimidine activity and on tumour angiogenesis.
2001 Aug 3
Randomised trial of SIR-Spheres plus chemotherapy vs. chemotherapy alone for treating patients with liver metastases from primary large bowel cancer.
2001 Dec
[Weekly low dose CPT-11 for multiple lung metastases of colon cancer on an out-patient treatment: a case report].
2001 Feb
Isolated hepatic perfusion for unresectable hepatic metastases from colorectal cancer.
2001 Feb
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.
2001 Jan 1
Apoptosis of haematopoietic cells upon thymidylate synthase inhibition is independent of p53 accumulation and CD95-CD95 ligand interaction.
2001 Jan 1
The significance of thymidine phosphorylase expression in colorectal cancer.
2001 Jan-Feb
[The efficacy of combination chemotherapy of 5'-deoxy-5-fluorouridine (5'-DFUR), cyclophosphamide (CPA) and medroxyprogesterone acetate (MPA) for bone metastasis in breast cancer patients].
2001 Jul
[A phase I study of docetaxel (TXT) and doxifluridine (5'-DFUR) combination therapy in patients with advanced and recurrent breast cancer].
2001 Jul
Phase I and pharmacologic study of i.v. hydroxyurea infusion given with i.p. 5-fluoro-2'-deoxyuridine and leucovorin.
2001 Jul
Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses.
2001 Jul 1
Thymidine phosphorylase expression and effect of doxifluridine: a phase II study.
2001 Jul-Aug
Intracavitary chemotherapy with 5-fluoro-2'-deoxyuridine (FdUrd) in malignant brain tumors.
2001 Jun
Preoperative chemoradiotherapy with oral doxifluridine plus low-dose oral leucovorin in unresectable primary rectal cancer.
2001 Jun 1
Therapeutic approaches to metastasis confined to the liver.
2001 Mar
Sequential intrahepatic and systemic fluoropyrimidine-based chemotherapy for metastatic colorectal cancer confined to the liver. A phase II study.
2001 May
Phase I study of hepatic arterial infusion of floxuridine and dexamethasone with systemic irinotecan for unresectable hepatic metastases from colorectal cancer.
2001 May 15
[Effect of peroral doxifluridine plus hepatic arterial infusion for synchronous liver metastasis of colorectal cancer--correlation with the expression of thymidine phosphorylase and dihydropyrimidine dehydrogenase in primary colorectal cancer lesions].
2001 Oct
Thymidine phosphorylase expression is useful in selecting adjuvant chemotherapy for stage III gastric cancer.
2001 Oct
[Combination chemotherapy of doxifluridine plus mitomycin C for colorectal lung metastasis--phase II study].
2001 Sep
Variations in 5-fluorouracil concentrations of colorectal tissues as compared with dihydropyrimidine dehydrogenase (DPD) enzyme activities and DPD messenger RNA levels.
2001 Sep
Three-dimensional organization of the hepatic microvasculature in hereditary hemorrhagic telangiectasia.
2001 Sep
Extrahepatic biliary stenoses after hepatic arterial infusion (HAI) of floxuridine (FUdR) for liver metastases from colorectal cancer.
2001 Sep-Oct
A randomized study comparing oral and standard regimens for metastatic breast cancer.
2001 Sep-Oct
[A case of long surviving advanced recurrent breast cancer with multiple bone metastases responding to treatment with 5'-DFUR combined with MPA].
2002 Feb
[Evidence for and practical use of arterial infusion chemotherapy for liver metastases].
2002 Feb
A controlled "before-after" study: impact of a clinical guidelines programme and regional cancer network organization on medical practice.
2002 Feb 1
CT-guided intratumoural administration of cisplatin/epinephrine gel for treatment of malignant liver tumours.
2002 Feb 12
[Adjuvant chemotherapy after curative resection for gastric cancer-5'-DFUR + cisplatin vs 5'-DFUR].
2002 Jan
[A 5'-DFUR + CPA + THP therapy that was effective for paclitaxel-refractory pulmonary metastasis of breast cancer--a case report].
2002 Jan
Systemic irinotecan and regional floxuridine after hepatic cytoreduction in 185 patients with unresectable colorectal cancer metastases.
2002 Mar
Fighting wars, winning battles.
2002 Mar
The effect of adjuvant 5'-deoxy-5-fluorouridine in early stage breast cancer patients: results from a multicenter randomized controlled trial.
2002 Mar
Isolation perfusion of the liver.
2002 Mar-Apr
Percutaneous vs. surgical placement of hepatic artery indwelling catheters for regional chemotherapy.
2002 Mar-Apr
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
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
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 Fri Jun 25 20:56:13 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:13 UTC 2021
Record UNII
039LU44I5M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLOXURIDINE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official 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
FUDR
Code 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
FLOXURIDINE [USP]
Common Name English
FLUORODEOXYURIDINE
Systematic Name English
2'-DEOXY-5-FLUOROURIDINE
Systematic Name English
Classification Tree Code System Code
WHO-ATC L01BC09
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
LIVERTOX 417
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NCI_THESAURUS C1557
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000180853
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
FDA ORPHAN DRUG 195104
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
Code System Code Type Description
MERCK INDEX
M5414
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY Merck Index
FDA UNII
039LU44I5M
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
CAS
50-91-9
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
MESH
D005467
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
PUBCHEM
5790
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
PRIMARY
WIKIPEDIA
FLOXURIDINE
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-072-5
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
IUPHAR
4801
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
DRUG CENTRAL
1184
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
DRUG BANK
DB00322
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
INN
2010
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
EPA CompTox
50-91-9
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
NCI_THESAURUS
C504
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
HSDB
3227
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
ChEMBL
CHEMBL917
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
RXCUI
4488
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1271008
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
PRIMARY USP-RS
EVMPD
SUB07659MIG
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY