Page last updated: 2024-11-08

5-fluoro-2'-deoxycytidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

5-fluoro-2'-deoxycytidine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID515328
CHEMBL ID1076257
SCHEMBL ID8345
MeSH IDM0051113

Synonyms (51)

Synonym
fcdr
nsc-48006
5-fluoro-2'-deoxycytidine
2'-deoxy-5-fluorocytidine
5-fluoro-2-deoxycytidine
5-fluorodeoxycytidine
10356-76-0
ro 5-1090
fdcyd
4-amino-5-fluoro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidin-2-one
4-amino-5-fluoro-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
2'-deoxy-5-fluorcytidine
5-fluor-desoxycytidin [german]
brn 0619209
nsc 48006
D3642
B86 ,
4-amino-5-fluoro-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
bdbm50311540
4-amino-5-fluoro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
2''-deoxy-5-fluorocytidine
CHEMBL1076257 ,
4-amino-1-[2-fluoro-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
A800762
unii-kua4693h5w
5-fluor-desoxycytidin
kua4693h5w ,
AKOS016002166
NCGC00346830-01
AKOS015853117
ro-5-1090
S2477
MLS006010723
smr004701686
SCHEMBL8345
3IPX
AC-32303
2'-deoxy-5-fluoro-cytidine
DTXSID2030437
5-fluoro-2'-deoxycytidine, >=98% (hplc), powder
4-amino-5-fluoro-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
AS-74677
DB12957
5-fluoro 2'-deoxycytidine
BCP18422
Q27282447
CS-0064397
ZB1480
HY-116217
cytidine,2'-deoxy-5-fluoro-
BP-58661

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic evaluation was carried out in cynomolgus monkeys in support of an ongoing phase I study of the PO combination of FdCyd and the CD inhibitor tetrahydrouridine (THU; NSC112907)."( Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans.
Beumer, JH; Covey, JM; Davis, M; Doroshow, JH; Eiseman, JL; Holleran, JL; Johnson, WD; Kummar, S; McCormick, DL; Newman, EM, 2015
)
0.42
" A pilot pharmacokinetic study was performed in humans to assess FdCyd bioavailability."( Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans.
Beumer, JH; Covey, JM; Davis, M; Doroshow, JH; Eiseman, JL; Holleran, JL; Johnson, WD; Kummar, S; McCormick, DL; Newman, EM, 2015
)
0.42
" FdCyd half-life ranged between 22 and 56 min, and clearance was approximately 15 mL/min/kg."( Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans.
Beumer, JH; Covey, JM; Davis, M; Doroshow, JH; Eiseman, JL; Holleran, JL; Johnson, WD; Kummar, S; McCormick, DL; Newman, EM, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" We aimed to characterize the pharmacokinetics, metabolism, and bioavailability of FdCyd with and without THU in mice."( Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice.
Beumer, JH; Covey, JM; Egorin, MJ; Eiseman, JL; Holleran, JL; Joseph, E; Parise, RA, 2006
)
0.33
"The oral bioavailability of FdCyd alone was approximately 4%."( Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice.
Beumer, JH; Covey, JM; Egorin, MJ; Eiseman, JL; Holleran, JL; Joseph, E; Parise, RA, 2006
)
0.33
"FdCyd is well absorbed but undergoes substantial first-pass catabolism by CD to potentially toxic metabolites that do not inhibit DNA methyltransferase."( Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice.
Beumer, JH; Covey, JM; Egorin, MJ; Eiseman, JL; Holleran, JL; Joseph, E; Parise, RA, 2006
)
0.33
" A co-crystal structure then allowed merging this series with a high throughput screening hit to afford a highly potent, selective and orally bioavailable inhibitor, compound 10."( Lead optimization and structure-based design of potent and bioavailable deoxycytidine kinase inhibitors.
Anderson, S; Augeri, DJ; Carlsen, M; Carson, KG; David Kimball, S; Finch, R; Foushee, AM; Fu, Q; Healy, JP; Heim-Riether, A; Hoffman, I; Hunter, M; Jessop, TC; Jhaver, K; Keyes, PE; Liu, Q; Miranda, M; Nouraldeen, A; Oravecz, T; Shen, M; Stouch, TR; Swaffield, JC; Swanson, RV; Tari, LW; Tarver, JE; Taylor, JA; Wilson, AG; Xu, A; Yu, XC, 2009
)
0.35
" FdCyd PO bioavailability after THU ranged between 9 and 25 % and increased with increasing THU dose."( Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans.
Beumer, JH; Covey, JM; Davis, M; Doroshow, JH; Eiseman, JL; Holleran, JL; Johnson, WD; Kummar, S; McCormick, DL; Newman, EM, 2015
)
0.42
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" In tumor tissue, optimal doses of FUra or FdUrd resulted in lower (a) FdUMP levels (5- to 2-fold), (b) RNA-level antimetabolites (6- to 3-fold), and (c) DNA-level antimetabolites (10- to 4-fold) compared to an optimal dosage of FdCyd plus H4Urd."( Tumor-selective metabolism of 5-fluoro-2'-deoxycytidine coadministered with tetrahydrouridine compared to 5-fluorouracil in mice bearing Lewis lung carcinoma.
Boothman, DA; Briggle, TV; Greer, S, 1987
)
0.27
"Animals were dosed intravenously (IV) or per os (PO)."( Oral and intravenous pharmacokinetics of 5-fluoro-2'-deoxycytidine and THU in cynomolgus monkeys and humans.
Beumer, JH; Covey, JM; Davis, M; Doroshow, JH; Eiseman, JL; Holleran, JL; Johnson, WD; Kummar, S; McCormick, DL; Newman, EM, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fumarate hydrataseHomo sapiens (human)Potency1.48180.00308.794948.0869AID1347053
EWS/FLI fusion proteinHomo sapiens (human)Potency0.05910.001310.157742.8575AID1259252; AID1259253; AID1259255; AID1259256
polyproteinZika virusPotency1.48180.00308.794948.0869AID1347053
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Deoxycytidine kinaseHomo sapiens (human)IC50 (µMol)0.12000.12000.12000.1200AID977608
Chain A, Deoxycytidine kinaseHomo sapiens (human)IC50 (µMol)0.12000.12000.12000.1200AID977608
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
pyrimidine nucleotide metabolic processDeoxycytidine kinaseHomo sapiens (human)
CMP biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
dAMP salvageDeoxycytidine kinaseHomo sapiens (human)
nucleoside phosphate biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
deoxyadenosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxycytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxyguanosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
ATP bindingDeoxycytidine kinaseHomo sapiens (human)
protein homodimerization activityDeoxycytidine kinaseHomo sapiens (human)
cytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID467456Inhibition of human dCK2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
5-Fluorocytosine derivatives as inhibitors of deoxycytidine kinase.
AID98851Compound was tested for percent increase in life span against L1210 lymphoid leukemia1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antitumor activity of fluorine-substituted 4-amino-2(1H)-pyridinones and their nucleosides. 3-Deazacytosines.
AID467457Inhibition of dCK in human CCRF-CEM assessed as inhibition of Ara-C phosphorylation2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
5-Fluorocytosine derivatives as inhibitors of deoxycytidine kinase.
AID1347411qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Lead optimization and structure-based design of potent and bioavailable deoxycytidine kinase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (33.33)18.7374
1990's13 (25.49)18.2507
2000's8 (15.69)29.6817
2010's7 (13.73)24.3611
2020's6 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (7.84%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (1.96%)4.05%
Observational0 (0.00%)0.25%
Other46 (90.20%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]