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
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00322Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/floxuridine.html
Sources: http://www.drugbank.ca/drugs/DB00322
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1952 Sources: http://www.drugbank.ca/drugs/DB00322 |
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Target ID: CHEMBL3160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?21330014 |
0.4 nM [IC50] | ||
Target ID: CHEMBL614353 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14716816 |
5.02 µM [IC50] | ||
Target ID: CHEMBL614909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14716816 |
12.45 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | FLOXURIDINE Approved UseFloxuridine 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 Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5547 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19147776 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
79304 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19147776 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19147776 |
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
Dose | Population | Adverse 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 |
DLT: Diarrhea... |
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 |
DLT: Diarrhea... |
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 |
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 Health Status: unhealthy Sources: |
Disc. AE: Fetal damage, Myocardial ischemia... AEs leading to discontinuation/dose reduction: Fetal damage Sources: Myocardial ischemia Stomatitis Esophagitis Leukopenia Vomiting Diarrhea Gastrointestinal ulcer Gastrointestinal bleeding Thrombocytopenia Hemorrhage |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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The significance of thymidine phosphorylase expression in colorectal cancer. | 2001 Jan-Feb |
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Role of the hMLH1 DNA mismatch repair protein in fluoropyrimidine-mediated cell death and cell cycle responses. | 2001 Jul 1 |
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Role of Bax in apoptosis of IL-3-dependent cells. | 2001 Jul 27 |
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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 |
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Locoregional therapy for liver metastases from colorectal cancer: the possibilities of intraarterial chemotherapy, and new hepatic-directed modalities. | 2001 Mar-Apr |
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Effects of concomitant use of doxifluridine, radiotherapy and immunotherapy in patients with advanced cervical cancer. | 2001 Mar-Apr |
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Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA. | 2001 May 1 |
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[Hepatic infusion of docetaxel using PEIT for a patient with stage IV breast cancer]. | 2001 Nov |
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Thymidine phosphorylase expression is useful in selecting adjuvant chemotherapy for stage III gastric cancer. | 2001 Oct |
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Inhibition of thymidylate synthase activity by antisense oligodeoxynucleotide and possible role in thymineless treatment. | 2001 Sep |
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Extrahepatic biliary stenoses after hepatic arterial infusion (HAI) of floxuridine (FUdR) for liver metastases from colorectal cancer. | 2001 Sep-Oct |
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Intrahepatic arterial infusion of chemotherapy: clinical results. | 2002 Apr |
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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 |
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Neoadjuvant chemotherapy with CPT-11 and cisplatin downstages locally advanced gastric cancer. | 2002 Mar-Apr |
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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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/floxuridine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15475457
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
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admin
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Record UNII |
039LU44I5M
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Record Status |
Validated (UNII)
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Record Version |
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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 |
NBK548421
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NCI_THESAURUS |
C1557
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NDF-RT |
N0000180853
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N0000007770
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FDA ORPHAN DRUG |
195104
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N0000007770
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N0000007770
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m5414
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039LU44I5M
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50-91-9
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100000081003
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D005467
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60761
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5790
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FLOXURIDINE
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200-072-5
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4801
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039LU44I5M
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1184
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DB00322
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1271008
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2010
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DTXSID3023057
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C504
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3227
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CHEMBL917
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4488
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27640
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SUB07659MIG
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METABOLITE ACTIVE -> PRODRUG |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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