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

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
gamma-Hydroxybutyric acid and 5-fluorouracil, metabolites of UFT, inhibit the angiogenesis induced by vascular endothelial growth factor.
2001
Bone morphogenetic protein-2, but not bone morphogenetic protein-7, promotes dendritic growth and calbindin phenotype in cultured rat striatal neurons.
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
[Clinical evaluation of effects and improvement in quality of life from palliative therapy of combination chemotherapy with Furtulon and consecutive low-dose cisplatin in cases of unresectable advanced gastrointestinal carcinoma].
2001 Feb
Combination of standard cytotoxic agents with polyamine analogues in the treatment of breast cancer cell lines.
2001 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
Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses.
2001 Jul 1
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
Preoperative chemoradiotherapy with oral doxifluridine plus low-dose oral leucovorin in unresectable primary rectal cancer.
2001 Jun 1
Locoregional therapy for liver metastases from colorectal cancer: the possibilities of intraarterial chemotherapy, and new hepatic-directed modalities.
2001 Mar-Apr
Sequential intrahepatic and systemic fluoropyrimidine-based chemotherapy for metastatic colorectal cancer confined to the liver. A phase II study.
2001 May
In vivo evaluation of 5-[(18)F]fluoro-2'-deoxyuridine as tracer for positron emission tomography in a murine pancreatic cancer model.
2001 May 15
Phase I study of hepatic arterial infusion of floxuridine and dexamethasone with systemic irinotecan for unresectable hepatic metastases from colorectal cancer.
2001 May 15
[Hepatic infusion of docetaxel using PEIT for a patient with stage IV breast cancer].
2001 Nov
Plasma, intestine and tumor levels of 5-fluorouracil in mice bearing L1210 ascites tumor following oral administration of 5-fluorouracil, UFT (mixed compound of tegafur and uracil), carmofur and 5'-deoxy-5-fluorouridine.
2001 Nov
Acquisition of human concentrative nucleoside transporter 2 (hcnt2) activity by gene transfer confers sensitivity to fluoropyrimidine nucleosides in drug-resistant leukemia cells.
2001 Nov
[A patient with recurrent breast cancer whose liver metastasis regressed following combined use of weekly docetaxel and MPA.5'-DFUR].
2001 Oct
[A case report of effective chemoradiation with 5'-DFUR and concomitant preoperative radiotherapy of the lower rectum].
2002 Apr
Intrahepatic arterial infusion of chemotherapy: clinical results.
2002 Apr
Intrahepatic arterial infusion of chemotherapy: pharmacologic principles.
2002 Apr
Downstaging of hepatocellular carcinoma and liver metastases from colorectal cancer by selective intra-arterial chemotherapy.
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
[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
Circadian chemotherapy for gynecological and genitourinary cancers.
2002 Jan
[Antimetastatic and antitumor effects of fluoropyrimidines alone and combined with taxanes in a murine model of breast cancer metastatic to the lung].
2002 Jan
[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
Use of 5-[(76)Br]bromo-2'-fluoro-2'-deoxyuridine as a ligand for tumour proliferation: validation in an animal tumour model.
2002 Jan
Biochemical and molecular effects of UCN-01 in combination with 5-fluorodeoxyuridine in A431 human epidermoid cancer cells.
2002 Mar
A phase II study of doxifluridine in elderly patients with advanced gastric cancer: the Japan Clinical Oncology Group Study (JCOG 9410).
2002 Mar
Overexpression of pyrimidine nucleoside phosphorylase enhances the sensitivity to 5'-deoxy-5-fluorouridine in tumour cells in vitro and in vivo.
2002 Mar
[Successful treatment of advanced recurent breast cancer using DMpC therapy as maintenance therapy].
2002 Mar
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
Echogenicity of liver metastases from colorectal carcinoma is an independent prognostic factor in patients treated with regional chemotherapy.
2002 Mar 15
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
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
Probable metabolic interaction of doxifluridine with phenytoin.
2002 May
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
Thymidine phosphorylase and dihydropyrimidine dehydrogenase levels in primary colorectal cancer show a relationship to clinical effects of 5'-deoxy-5-fluorouridine as adjuvant chemotherapy.
2002 May-Jun
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
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
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NDF-RT N0000007770
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NDF-RT N0000007770
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NDF-RT N0000007770
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NDF-RT N0000007770
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LIVERTOX 417
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NCI_THESAURUS C1557
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NDF-RT N0000180853
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NDF-RT N0000007770
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FDA ORPHAN DRUG 195104
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NDF-RT N0000007770
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NDF-RT N0000007770
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Code System Code Type Description
MERCK INDEX
M5414
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PRIMARY Merck Index
FDA UNII
039LU44I5M
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PRIMARY
CAS
50-91-9
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PRIMARY
MESH
D005467
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PRIMARY
PUBCHEM
5790
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PRIMARY
WIKIPEDIA
FLOXURIDINE
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PRIMARY
ECHA (EC/EINECS)
200-072-5
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PRIMARY
IUPHAR
4801
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PRIMARY
DRUG CENTRAL
1184
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PRIMARY
DRUG BANK
DB00322
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PRIMARY
INN
2010
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PRIMARY
EPA CompTox
50-91-9
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PRIMARY
NCI_THESAURUS
C504
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PRIMARY
HSDB
3227
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PRIMARY
ChEMBL
CHEMBL917
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PRIMARY
RXCUI
4488
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PRIMARY RxNorm
USP_CATALOG
1271008
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PRIMARY USP-RS
EVMPD
SUB07659MIG
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PRIMARY