Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11FN2O5 |
Molecular Weight | 246.1924 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@@H](F)[C@@H]1O)N2C=CC(=O)NC2=O
InChI
InChIKey=UIYWFOZZIZEEKJ-PXBUCIJWSA-N
InChI=1S/C9H11FN2O5/c10-6-7(15)4(3-13)17-8(6)12-2-1-5(14)11-9(12)16/h1-2,4,6-8,13,15H,3H2,(H,11,14,16)/t4-,6+,7-,8-/m1/s1
1-(2-DEOXY-2-FLUORO-β-D-ARABINOFURANOSYL)URACIL (FAU) is a thymidine analog. In several cancer cell lines, FAU was phosphorylated intracellularly to its monophosphate, 1-(2-deoxy-2-fluoro--Darabinofuranosyl) uracil monophosphate (FAUMP), by thymidine kinase and methylated in the 5-position by thymidylate synthase to form the product, 1-(2-deoxy-2-fluoro- -D-arabinofuranosyl) 5-methyluracil monophosphate (FMAUMP). FAU strongly inhibits the growth of tumor cells with high thymidylate synthase activity. FAU had been in phase I clinical trial for the treatment of advanced solid tumors.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15475457
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.
Originator
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1152 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22410089 |
50 mg/m² 1 times / week multiple, intravenous dose: 50 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1479 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22410089 |
50 mg/m² single, intravenous dose: 50 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22410089 |
50 mg/m² 1 times / week multiple, intravenous dose: 50 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FMAU plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22410089 |
50 mg/m² single, intravenous dose: 50 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
FMAU plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Fialuridine and its metabolites inhibit DNA polymerase gamma at sites of multiple adjacent analog incorporation, decrease mtDNA abundance, and cause mitochondrial structural defects in cultured hepatoblasts. | 1996 Apr 16 |
|
Radiolabeled 2'-fluorodeoxyuracil-beta-D-arabinofuranoside (FAU) and 2'-fluoro-5-methyldeoxyuracil-beta -D-arabinofuranoside (FMAU) as tumor-imaging agents in mice. | 2002 May |
|
Distribution of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) uracil in mice bearing colorectal cancer xenografts: rationale for therapeutic use and as a positron emission tomography probe for thymidylate synthase. | 2004 Oct 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11976837
Mice: In 25% ethanol 5 ul/g (0.74 mg/kg (0.16 uCi/g))
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15475457
Coincubation of [3H]-FAU (43 nM/l) in vitro with 50 nmol/L FdUrd
decreased FAU incorporation into DNA by 70% in HT29 and
84% in LS174T.
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NCI_THESAURUS |
C1557
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3007908
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K7386OMP29
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C80036
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69123-94-0
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678515
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DTXSID20219192
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SUBSTANCE RECORD