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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
Structure of 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)URACIL

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

HIDE SMILES / InChI

Description

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

CNS Penetrant
2,554

Originator

Perlman, M.E. et al.
1

Approval Year

Unknown
139,594

Targets

Primary TargetPharmacologyConditionPotency
Thymidylate synthase
32
Inhibitor
8,297

Conditions

ConditionModalityTargetsHighest PhaseProduct
Solid tumors
145
 Primary
Phase I
428
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1152 ng/mL
50 mg/m² 1 times / week multiple, intravenous
 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)URACIL plasma
Homo sapiens
1479 ng/mL
50 mg/m² single, intravenous
 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)URACIL plasma
Homo sapiens
4.1 ng/mL
50 mg/m² 1 times / week multiple, intravenous
 FMAU plasma
Homo sapiens
2.1 ng/mL
50 mg/m² single, intravenous
 FMAU plasma
Homo sapiens

PubMed

Patents

EP0666749B1
1
US8076531
1
WO2013167743A1
14

Sample Use Guides

In Vivo Use Guide
Mice: In 25% ethanol 5 ul/g (0.74 mg/kg (0.16 uCi/g))
Route of Administration: Intravenous
In Vitro Use Guide
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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