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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H12FN3O4
Molecular Weight 245.208
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5-FLUORO-2'-DEOXYCYTIDINE

SMILES

C1[C@@]([H])([C@@]([H])(CO)O[C@@]1([H])n2cc(c(=N)nc2O)F)O

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 245.208
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
120.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Synthesis and anticancer and antiviral activities of various 2'- and 3'-methylidene-substituted nucleoside analogues and crystal structure of 2'-deoxy-2'-methylidenecytidine hydrochloride.
1991 Aug
Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases.
2002 Aug 23
Covalent DNA display as a novel tool for directed evolution of proteins in vitro.
2004 Sep
Capecitabine: an evidence-based review of its effectiveness in the treatment of carcinoma of the pancreas.
2007 Nov 30
DNA mismatch repair (MMR)-dependent 5-fluorouracil cytotoxicity and the potential for new therapeutic targets.
2009 Oct
Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine.
2010 Aug 24
Patents

Sample Use Guides

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
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 Sat Jun 26 11:17:39 UTC 2021
Edited
by admin
on Sat Jun 26 11:17:39 UTC 2021
Record UNII
KUA4693H5W
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
Code System Code Type Description
EPA CompTox
10356-76-0
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
FDA UNII
KUA4693H5W
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
PUBCHEM
515328
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
MESH
C007746
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
EVMPD
SUB33650
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
DRUG BANK
DB12957
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
CAS
10356-76-0
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
NCI_THESAURUS
C62785
Created by admin on Sat Jun 26 11:17:39 UTC 2021 , Edited by admin on Sat Jun 26 11:17:39 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG