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Floxuridine
[CAS# 50-91-9]

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Complete supplier list of Floxuridine
Identification
Classification API >> Antineoplastic agents >> Antimetabolite antineoplastic
Name Floxuridine
Synonyms Fluorodeoxyuridine; Fluoruridine deoxyribose; 2'-Deoxy-5-fluorouridine; (+)-5-Fluoro-2'-deoxyuridine
Molecular Structure CAS # 50-91-9, Floxuridine, Fluorodeoxyuridine, Fluoruridine deoxyribose, 2'-Deoxy-5-fluorouridine, (+)-5-Fluoro-2'-deoxyuridine
Protein Sequence N
Molecular Formula C9H11FN2O5
Molecular Weight 246.19
CAS Registry Number 50-91-9
EC Number 200-072-5
SMILES C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)CO)O
Properties
Solubility Soluble 100 mM (water), 100 mM (DMSO) (Expl.)
Density 1.6±0.1 g/cm3, Calc.*
Melting point 148 ºC (Expl.)
alpha 35.9 º (c=1, water)
Index of Refraction 1.609, Calc.*
Boiling Point 150 ºC (Expl.)
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol   GHS06;GHS08 Danger    Details
Hazard Statements H301-H341    Details
Precautionary Statements P203-P264-P270-P280-P301+P316-P318-P321-P330-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H301
Skin irritationSkin Irrit.2H315
Germ cell mutagenicityMuta.2H341
Eye irritationEye Irrit.2AH319
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H312
Reproductive toxicityRepr.1BH360
Acute toxicityAcute Tox.3H311
Eye irritationEye Irrit.2H319
Acute toxicityAcute Tox.4H302
Acute toxicityAcute Tox.3H331
Transport Information UN 2811
SDS Available
up Discovory and Applicatios
Floxuridine is a chemotherapeutic agent used primarily in the treatment of cancer. It is a synthetic nucleoside analog of thymidine and belongs to the class of drugs known as antimetabolites. Floxuridine is utilized in the treatment of colorectal cancer and other solid tumors, particularly when the cancer has metastasized to the liver.

Floxuridine was first synthesized and introduced in the mid-20th century as part of the efforts to develop drugs that could interfere with DNA synthesis and inhibit cancer cell proliferation. Its structure, a fluorinated derivative of deoxyuridine, was designed to mimic the nucleosides naturally involved in DNA replication. The presence of the fluorine atom in the molecule gives it its therapeutic properties, as it can be incorporated into the DNA of rapidly dividing cells, leading to DNA damage and cell death.

The action of floxuridine is primarily through its interference with thymidylate synthase, an enzyme critical for the synthesis of thymidine monophosphate, a precursor to thymidine, one of the four building blocks of DNA. When floxuridine is incorporated into the DNA of cancer cells, it disrupts DNA replication and leads to cell death, specifically targeting cells that are rapidly dividing, such as tumor cells. This mechanism of action makes floxuridine effective in the treatment of cancers that are characterized by uncontrolled cell proliferation.

Floxuridine is typically administered as an intravenous injection or infused into the hepatic artery, especially for cancers that have metastasized to the liver. This method of administration ensures that the drug is delivered directly to the liver, maximizing its effectiveness while minimizing systemic side effects. The drug is often used in conjunction with other cancer treatments, such as surgery, radiation therapy, and other chemotherapeutic agents, to improve overall treatment outcomes.

The drug is commonly used in the treatment of liver metastases from colorectal cancer. It has been shown to be effective in reducing the size of tumors and alleviating symptoms in patients with advanced liver metastases. Floxuridine has also been studied for its potential in treating other solid tumors, including those of the pancreas and stomach. In some cases, it is used as part of a palliative treatment regimen to improve quality of life for patients with advanced cancer.

Floxuridine, like other chemotherapy agents, can have significant side effects. These include bone marrow suppression, nausea, vomiting, and gastrointestinal distress. The drug’s effects on rapidly dividing cells are not limited to cancer cells, which can lead to damage to normal, healthy cells, particularly those in the gastrointestinal tract and bone marrow. As a result, its use requires careful monitoring, particularly for signs of myelosuppression, a reduction in the production of blood cells. Despite these potential side effects, floxuridine has been an important tool in the management of certain cancers, particularly when liver metastasis is involved.

In conclusion, floxuridine is a vital chemotherapeutic agent used in the treatment of cancers, especially those with liver metastases. Its mechanism of action involves the disruption of DNA synthesis, leading to the death of rapidly dividing cancer cells. While it is an effective treatment for specific types of cancer, its use requires careful monitoring due to potential side effects. The development of floxuridine marked an important advance in cancer therapy, providing a valuable option for patients with advanced disease.
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