5-FLUORO-2'-DEOXYCYTIDINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12FN3O4
Molecular Weight	245.2077
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

InChIKey=IDYKCXHJJGMAEV-RRKCRQDMSA-N

InChI=1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H12FN3O4
Molecular Weight	245.2077
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25567350
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT00978250 | https://www.ncbi.nlm.nih.gov/pubmed/19836229 | https://clinicaltrials.gov/ct2/show/NCT01041443 | https://www.ncbi.nlm.nih.gov/pubmed/23397046

5-Fluoro-2-deoxycytidine is a fluorinated pyrimidine analog antimetabolite with potential antineoplastic activity. As a prodrug, 5-fluoro-2-deoxycytidine is converted by intracellular deaminases to the cytotoxic agent 5-fluorouracil (5-FU). 5-FU is subsequently metabolized to active metabolites including 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). FdUMP binds to and inhibits thymidylate synthase, thereby reducing the production of thymidine monophosphate, which leads to depletion of thymidine triphosphate and the inhibition of DNA synthesis and cell division. FUTP competes with uridine triphosphate (UTP) for incorporation into the RNA strand, which results in the inhibition of RNA and protein synthesis and cell proliferation. 5-Fluoro-2-deoxycytidine undergoing trials to test its effectiveness in treating cancer that has not responded to standard therapies.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Deoxycytidine kinase 6 Target ID: CHEMBL2447 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19836229	Inhibitor 8297		120.0 µM [IC50]
DNA methylation 1 Target ID: GO:0006306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23397046	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Head and neck cancer 50 Sources: https://clinicaltrials.gov/ct2/show/NCT00978250	Primary	Phase II 1132	Unknown Approved Use Unknown
Lung cancer 69 Sources: https://clinicaltrials.gov/ct2/show/NCT00978250	Primary	Phase II 1132	Unknown Approved Use Unknown
Urinary bladder neoplasms 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00978250	Primary	Phase II 1132	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://clinicaltrials.gov/ct2/show/NCT00978250	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34125	https://www.001chemical.com/chem/search?q=DY34125
1PlusChem LLC	1P008633	https://www.1pchem.com/search?query=1P008633
A2B Chem	AD80335	http://a2bchem.com/prod/AD80335
AK Scientific	0860AA	https://aksci.com/item_detail.php?cat=0860AA
Angene	AGN-PC-0NVL6X	http://www.angenechemical.com/productshow/AGN-PC-0NVL6X.html
AstaTech	C14053	http://astatechinc.com/CPSResult.php?CRNO=C14053
BOC Sciences	10356-76-0	http://www.bocsci.com/description.asp?cas=10356-76-0
BioSynth	W-200702	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-200702
Chem Scene	CS-0064397	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0064397
Combi-Blocks	QG-9600	http://www.combi-blocks.com/cgi-bin/find.cgi?QG-9600
Fluorochem	222059	http://www.fluorochem.co.uk/Products/Product?code=222059
KeyOrganics	AS-74677	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74677
Lab Network	LN01364956	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01364956
Lab Seeker	SC-54218	http://www.labseeker.com/search.php?keywords=SC-54218&category=0
LabSeeker	SC-54218	http://www.labseeker.com/search.php?keywords=SC-54218&category=0
MolPort	MolPort-003-986-182	https://www.molport.com/shop/molecule-link/MolPort-003-986-182
Molcore	MC34125	http://www.molcore.com/CatMC34125.html
ShangHai Biochempartner	BCP18422	http://www.biochempartner.com/search_BCP18422
Tetrahedron	TS93010	http://www.thsci.com/search.do?q=TS93010
TimTec	ST50440772	http://www.echemstore.com/catalogsearch/result/?q=ST50440772
Toronto Research Chemicals	F590803	https://www.trc-canada.com/product-detail/?CatNum=F590803
W&J PharmaChem	50C984770	http://wjpharmachem.com/new/searcht.php?keyword=50C984770
eMolecules	3718067	https://orderbb.emolecules.com/search/#?query=3718067
eNovation Chemicals	K89410	https://www.enovationchem.com/Products.asp?SEARCHTEXT=K89410&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-8582877770	https://mcule.com/MCULE-8582877770/

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

5-Fluoro-2-Deoxycytidine (100 mg/m2) + Tetrahydrouridine (350 mg/m2) administered 5 days/week for 2 weeks in 28-daycycles

Route of Administration: Intravenous

In Vitro Use Guide

HCT116 and U2OS cells were used for activity evaluation. Cells were split at 1Ч103 cells per well in 96-well plate. After 24 h cells were treated with drugs (5-Fluoro-2-deoxycytidine 0.1-10mkM) and cultured for 72 h. 25 μg MTT was then added to each well and cells incubated for 4 h at 37°C. The medium with the formazan sediment was dissolved in 50% DMF and 30% SDS (pH4.7). The absorption was read at 570nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:02 UTC 2023` Edited by `admin` on `Fri Dec 15 15:58:02 UTC 2023`
Record UNII	KUA4693H5W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-FLUORO-2'-DEOXYCYTIDINE

Systematic Name

English

CYTIDINE, 2'-DEOXY-5-FLUORO-

Systematic Name

English

5-FLUORO-2-DEOXYCYTIDINE

Common Name

English

RO-5-1090

Code

English

NSC-48006

Code

English

RO 5-1090

Code

English

5-FLUORODEOXYCYTIDINE

Systematic Name

English

FDCYD

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557