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

Investigational

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

Structure Search

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

Molecular Formula	C9H11FN2O5
Molecular Weight	246.1924
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11976837 | https://www.ncbi.nlm.nih.gov/pubmed/15475457 | http://adisinsight.springer.com/drugs/800013961

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thymidylate synthase 33 Target ID: Thymidylate synthase Sources: https://www.ncbi.nlm.nih.gov/pubmed/11976837 \| http://adisinsight.springer.com/drugs/800013961 \| http://en.pharmacodia.com/web/drug/1_18568.html	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Solid tumors 147 Sources: http://adisinsight.springer.com/drugs/800013961 http://en.pharmacodia.com/web/drug/1_18568.html	Primary		Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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
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
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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P005Y8C	https://www.1pchem.com/search?query=1P005Y8C
AA Blocks	AA0035T1	http://aablocks.com/goods/Goods/detail?id=AA0035T1
AbovChem LLC	AC360037	http://www.abovchem.com/pc/en/product_list.aspx?wd=AC360037
Achemo Scientific Limited	AC-75359	http://www.achemo.com/search/?Keyword=AC-75359
AK Scientific	0661AC	https://aksci.com/item_detail.php?cat=0661AC
AK Scientific	AMTA035	https://aksci.com/item_detail.php?cat=AMTA035
Angene	AGN-PC-0TUQ4M	http://www.angenechemical.com/productshow/AGN-PC-0TUQ4M.html
Apollo Scientific	PC56119	http://www.apolloscientific.co.uk/chemical_results.php?qstext=PC56119&product_group=%25&search_fieldname=header_search
AstaTech	F12922	http://astatechinc.com/CPSResult.php?CRNO=F12922
BioSynth	W-203534	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-203534
BOC Sciences	69123-94-0	http://www.bocsci.com/description.asp?cas=69123-94-0
ChemShuttle	138965	https://www.chemshuttle.com/catalogsearch/result/?q=138965
Combi-Blocks	QB-9865	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-9865
eMolecules	206905852	https://orderbb.emolecules.com/search/#?query=206905852
eMolecules	2735987	https://orderbb.emolecules.com/search/#?query=2735987
eMolecules	29257306	https://orderbb.emolecules.com/search/#?query=29257306
eMolecules	30315891	https://orderbb.emolecules.com/search/#?query=30315891
eNovation Chemicals	D592328	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D592328&searchbtn.x=0&searchbtn.y=0
Fluorochem	239660	http://www.fluorochem.co.uk/Products/Product?code=239660
Lab Network	LN01330373	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01330373
mcule	MCULE-3215023061	https://mcule.com/MCULE-3215023061/
mcule	MCULE-5835219554	https://mcule.com/MCULE-5835219554/
MolPort	MolPort-005-938-296	https://www.molport.com/shop/molecule-link/MolPort-005-938-296
MolPort	MolPort-020-000-359	https://www.molport.com/shop/molecule-link/MolPort-020-000-359
MuseChem	R050790	https://www.musechem.com/product/R050790.html
PI Chemicals	PI-40081	http://www.pipharm.com/catalog_products/PI-40081.html
SynQuest	4H59-3-00	http://www.synquestlabs.com/search-result.html?q=4H59-3-00
Tetrahedron	TS62270	http://www.thsci.com/search.do?q=TS62270
Toronto Research Chemicals	D239968	https://www.trc-canada.com/product-detail/?CatNum=D239968
Toronto Research Chemicals	F590275	https://www.trc-canada.com/product-detail/?CatNum=F590275
Toronto Research Chemicals	M260517	https://www.trc-canada.com/product-detail/?CatNum=M260517
Wonderchem	WD0448Z	http://www.wonder-chem.com/search.html?text=WD0448Z

PubMed

Title	Date	PubMed
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.	2004-10-01	15475457
Imaging [18F]FAU [1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl) uracil] in dogs.	2003-01	12493539
Radiolabeled 2'-fluorodeoxyuracil-beta-D-arabinofuranoside (FAU) and 2'-fluoro-5-methyldeoxyuracil-beta -D-arabinofuranoside (FMAU) as tumor-imaging agents in mice.	2002-05	11976837
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.	1996-04-16	8622980

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:45:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:45:25 GMT 2025`
Record UNII	K7386OMP29
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

2'-F-ARA-DEOXYURIDINE

Preferred Name

English

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

Common Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-

Common Name

English

2'-FLUORO-ARA-DEOXYURIDINE

Common Name

English

FAU

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557