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 32 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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Solid tumors 145 Sources: http://adisinsight.springer.com/drugs/800013961 http://en.pharmacodia.com/web/drug/1_18568.html	Primary		Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	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

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
AK Scientific	0661AC	https://aksci.com/item_detail.php?cat=0661AC
AK Scientific	AMTA035	https://aksci.com/item_detail.php?cat=AMTA035
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
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
BOC Sciences	69123-94-0	http://www.bocsci.com/description.asp?cas=69123-94-0
BioSynth	W-203534	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-203534
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
Fluorochem	239660	http://www.fluorochem.co.uk/Products/Product?code=239660
Lab Network	LN01330373	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01330373
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
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
mcule	MCULE-3215023061	https://mcule.com/MCULE-3215023061/
mcule	MCULE-5835219554	https://mcule.com/MCULE-5835219554/

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	8622980
Radiolabeled 2'-fluorodeoxyuracil-beta-D-arabinofuranoside (FAU) and 2'-fluoro-5-methyldeoxyuracil-beta -D-arabinofuranoside (FMAU) as tumor-imaging agents in mice.	2002 May	11976837
Imaging [18F]FAU [1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl) uracil] in dogs.	2003 Jan	12493539
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	15475457

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 `Fri Dec 15 17:22:16 GMT 2023` Edited by `admin` on `Fri Dec 15 17:22:16 GMT 2023`
Record UNII	K7386OMP29
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Common Name

English

2'-F-ARA-DEOXYURIDINE

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