Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2020-02-26 21:39:43 UTC |
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HMDB ID | HMDB0014467 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Floxuridine |
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Description | Floxuridine, also known as 5FDU or FUDR, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Floxuridine is a drug which 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 is available as a sterile, nonpyrogenic, lyophilized powder for reconstitution. An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection. Floxuridine is an anti-metabolite or a pyrimidine analog that works by disrupting the process S-phase of cell division, selectively targeting rapidly dividing cells. Floxuridine is an extremely weak basic (essentially neutral) compound (based on its pKa). Floxuridine exists in all living organisms, ranging from bacteria to humans. 5-Fluorouracil primarily works by interfering with DNA synthesis; however, it may also inhibit the formation of fraudulent RNA via physical incorporation into the RNA. After successful biotransformation, floxuridine is converted into an active component, flurouracil, which blocks the enzyme which converts cytosine nucleosides into the deoxy derivative. Oral, rat LD50: 215 mg/kg. |
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Structure | |
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Synonyms | Value | Source |
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1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil | ChEBI | 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil | ChEBI | 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil | ChEBI | 2'-Deoxy-5-fluorouridine | ChEBI | 5-Fluoro-2'-deoxyuridine | ChEBI | 5-Fluoro-2-desoxyuridine | ChEBI | 5-Fluorodeoxyuridine | ChEBI | 5-Fluorouracil 2'-deoxyriboside | ChEBI | 5-Fluorouracil deoxyriboside | ChEBI | 5FDU | ChEBI | beta-5-Fluoro-2'-deoxyuridine | ChEBI | Deoxyfluorouridine | ChEBI | FdU | ChEBI | Floxiridina | ChEBI | Floxuridin | ChEBI | Floxuridinum | ChEBI | Fluorodeoxyuridine | ChEBI | Fluoruridine deoxyribose | ChEBI | FUDR | Kegg | 1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil | Generator | 1-(2-Deoxy-β-D-ribofuranosyl)-5-fluorouracil | Generator | 1-b-D-2'-Deoxyribofuranosyl-5-flurouracil | Generator | 1-Β-D-2'-deoxyribofuranosyl-5-flurouracil | Generator | 1b-D-2'-Deoxyribofuranosyl-5-flurouracil | Generator | 1Β-D-2'-deoxyribofuranosyl-5-flurouracil | Generator | b-5-Fluoro-2'-deoxyuridine | Generator | Β-5-fluoro-2'-deoxyuridine | Generator | 5 Fluorodeoxyuridine | HMDB | FDUR | HMDB | FDURD | HMDB | 5-FUdR | HMDB |
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Chemical Formula | C9H11FN2O5 |
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Average Molecular Weight | 246.1924 |
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Monoisotopic Molecular Weight | 246.065199677 |
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IUPAC Name | 5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | floxuridine |
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CAS Registry Number | 50-91-9 |
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SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O |
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InChI Identifier | 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 |
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InChI Key | ODKNJVUHOIMIIZ-RRKCRQDMSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Pyrimidine 2'-deoxyribonucleosides |
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Direct Parent | Pyrimidine 2'-deoxyribonucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine 2'-deoxyribonucleoside
- Halopyrimidine
- Hydroxypyrimidine
- Pyrimidone
- Aryl fluoride
- Aryl halide
- Hydropyrimidine
- Pyrimidine
- Heteroaromatic compound
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Alcohol
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organofluoride
- Organohalogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 150.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 40.8 g/L | Not Available | LogP | -1.4 | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00lr-9600000000-155a97133c7827d2a1ce | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-3900000000-44f00976f508bab47f36 | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-00kb-2910000000-2efae68e874a5fdba01c | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00lr-9600000000-155a97133c7827d2a1ce | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-3900000000-44f00976f508bab47f36 | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-00kb-2910000000-2efae68e874a5fdba01c | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0036-9340000000-625fd93cccce9bbf8234 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0gk9-8926000000-e5bea4ee2a8fa95520d5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-e75f17c5e6c58cb63cc4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-1900000000-ab9d2ecf3f514e6cd7fd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01q9-7900000000-5b44e036090ffa5616c4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ikd-5890000000-537ea470ce67d29de875 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056r-2930000000-9edc79b79e109479fd9b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-8d9d5de0ec79de7d99fd | Spectrum |
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