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
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
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 |
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 |
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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 Date9.5489281E11 |
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 Co-administed with:: leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6) Sources: Page: p.263 |
unhealthy, 30-79 n = 3 Health Status: unhealthy Condition: Carcinoma Age Group: 30-79 Sex: M+F Population Size: 3 Sources: Page: p.263 |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 4, 50%) Sources: Page: p.263 |
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 Co-administed with:: leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6) Sources: Page: p.263 |
unhealthy, 30-79 n = 6 Health Status: unhealthy Condition: Carcinoma Age Group: 30-79 Sex: M+F Population Size: 6 Sources: Page: p.263 |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3, 33.3%) Sources: Page: p.263 |
544 mg/m2 5 times / day multiple, intraarterial (mean) MTD Dose: 544 mg/m2, 5 times / day Route: intraarterial Route: multiple Dose: 544 mg/m2, 5 times / day Co-administed with:: 5-FU, i.v(6025 mg/m2/cycle (5 days)) Sources: Page: p.390 |
unhealthy, 44-75 n = 29 Health Status: unhealthy Condition: Gastrointestinal adenocarcinoma metastatic to the liver Age Group: 44-75 Sex: M+F Population Size: 29 Sources: Page: p.390 |
DLT: Mucositis... Dose limiting toxicities: Mucositis (grade 3-4, 72%) Sources: Page: p.390 |
0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver 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 Co-administed with:: leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6) Sources: Page: p.263 |
unhealthy, 30-79 n = 3 Health Status: unhealthy Condition: Carcinoma Age Group: 30-79 Sex: M+F Population Size: 3 Sources: Page: p.263 |
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 Co-administed with:: leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6) Sources: Page: p.263 |
unhealthy, 30-79 n = 6 Health Status: unhealthy Condition: Carcinoma Age Group: 30-79 Sex: M+F Population Size: 6 Sources: Page: p.263 |
Mucositis | grade 3-4, 72% DLT |
544 mg/m2 5 times / day multiple, intraarterial (mean) MTD Dose: 544 mg/m2, 5 times / day Route: intraarterial Route: multiple Dose: 544 mg/m2, 5 times / day Co-administed with:: 5-FU, i.v(6025 mg/m2/cycle (5 days)) Sources: Page: p.390 |
unhealthy, 44-75 n = 29 Health Status: unhealthy Condition: Gastrointestinal adenocarcinoma metastatic to the liver Age Group: 44-75 Sex: M+F Population Size: 29 Sources: Page: p.390 |
Diarrhea | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Esophagitis | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Fetal damage | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Gastrointestinal bleeding | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Gastrointestinal ulcer | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Hemorrhage | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Leukopenia | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Myocardial ischemia | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Stomatitis | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Thrombocytopenia | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
Vomiting | Disc. AE | 0.6 mg/kg 1 times / day multiple, intraarterial (max) 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 Condition: Gastrointestinal adenocarcinoma metastatic to the liver Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[Preoperative chemotherapy for advanced colorectal carcinomas--comparison of histological effect between 5'-DFUR + leucovorin tablet and 5'-DFUR alone]. | 2001 Apr |
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Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 2001 Apr |
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Randomised trial of SIR-Spheres plus chemotherapy vs. chemotherapy alone for treating patients with liver metastases from primary large bowel cancer. | 2001 Dec |
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Surgical debulking and intraperitoneal chemotherapy for established peritoneal metastases from colon and appendix cancer. | 2001 Dec |
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Surgery as adjuvant therapy? The treatment of peritoneal metastases from gastrointestinal malignancy. | 2001 Dec |
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Antisense-induced down-regulation of thymidylate synthase and enhanced cytotoxicity of 5-FUdR in 5-FUdR-resistant HeLa cells. | 2001 Dec |
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Regional chemotherapy of nonresectable colorectal liver metastases with mitoxantrone, 5-fluorouracil, folinic acid, and mitomycin C may prolong survival. | 2001 Dec 1 |
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Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs. | 2001 Dec 6 |
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[Advanced breast cancer with multiple bone metastases successfully treated with combined chemoendocrine-therapy of CEF (cyclophosphamide, epirubicin, 5-fluorouracil) and 5'-DFUR (5'-deoxy-5-fluorouridine) + MPA (medroxyprogesterone acetate)--a case report]. | 2001 Feb |
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[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 |
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[A phase I study of docetaxel (TXT) and doxifluridine (5'-DFUR) combination therapy in patients with advanced and recurrent breast cancer]. | 2001 Jul |
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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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Malnutrition and cachexia in ovarian cancer patients: pathophysiology and management. | 2001 Jul-Aug |
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Intracavitary chemotherapy with 5-fluoro-2'-deoxyuridine (FdUrd) in malignant brain tumors. | 2001 Jun |
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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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Preoperative chemoradiotherapy with oral doxifluridine plus low-dose oral leucovorin in unresectable primary rectal cancer. | 2001 Jun 1 |
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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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Survival benefits of adjuvant chemotherapy with oral doxifluridine (5'-DFUR) following radiotherapy in patients with unresectable pancreatic cancer. | 2001 Nov |
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[A case of lung metastasis from colon cancer treated successfully with combined chemotherapy of CPT-11 and 5'-DFUR]. | 2001 Nov |
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[Hepatic infusion of docetaxel using PEIT for a patient with stage IV breast cancer]. | 2001 Nov |
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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 |
|
Interaction of thymidylate synthase with the 5'-thiophosphates, 5'-dithiophosphates, 5'-H-phosphonates and 5'-S-thiosulfates of 2'-deoxyuridine, thymidine and 5-fluoro-2'-deoxyuridine. | 2001 Oct |
|
Combined effects of docetaxel and fluoropyrimidines on tumor growth and expression of interleukin-6 and thymidine phosphorylase in breast cancer xenografts. | 2001 Oct |
|
[A patient with recurrent breast cancer whose liver metastasis regressed following combined use of weekly docetaxel and MPA.5'-DFUR]. | 2001 Oct |
|
Thymidine phosphorylase expression is useful in selecting adjuvant chemotherapy for stage III gastric cancer. | 2001 Oct |
|
Variations in 5-fluorouracil concentrations of colorectal tissues as compared with dihydropyrimidine dehydrogenase (DPD) enzyme activities and DPD messenger RNA levels. | 2001 Sep |
|
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 |
|
[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 |
|
[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 |
|
Immunohistochemical variation of human equilibrative nucleoside transporter 1 protein in primary breast cancers. | 2002 Jan |
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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 |
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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 |
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Echogenicity of liver metastases from colorectal carcinoma is an independent prognostic factor in patients treated with regional chemotherapy. | 2002 Mar 15 |
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Isolation perfusion of the liver. | 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 |
|
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 |
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
by
admin
on
Edited
Fri Jun 25 20:56:13 UTC 2021
by
admin
on
Fri Jun 25 20:56:13 UTC 2021
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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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Classification Tree | Code System | Code | ||
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WHO-ATC |
L01BC09
Created by
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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 | ||
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M5414
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PRIMARY | Merck Index | ||
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039LU44I5M
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50-91-9
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D005467
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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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1184
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DB00322
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2010
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50-91-9
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C504
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3227
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CHEMBL917
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4488
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PRIMARY | RxNorm | ||
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1271008
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PRIMARY | USP-RS | ||
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SUB07659MIG
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PRIMARY |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |