Page last updated: 2024-12-07

2',2'-difluorodeoxycytidine 5'-triphosphate

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

Cross-References

ID SourceID
PubMed CID130659
CHEMBL ID1201383
CHEBI ID178151
SCHEMBL ID3468704
MeSH IDM0153651

Synonyms (29)

Synonym
2,2-df-ctp
unii-a0q7so4oze
cytidine 5'-(tetrahydrogen triphosphate), 2'-deoxy-2',2'-difluoro-
a0q7so4oze ,
[[(2r,3r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-diluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
CHEBI:178151
gemcitabine triphosphate
110988-86-8
CHEMBL1201383
2',2'-difluorodeoxycytidine 5'-triphosphate
dfdctp
phosphoric acid tri-[(2r,3r,5r)-5-(4-amino-2-oxo-2h-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
[[(2r,3r,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
GTF ,
2'-deoxy-2',2'-difluorocytidine 5'-(tetrahydrogen triphosphate)
[[(2r,3r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
SCHEMBL3468704
2'-deoxy-2',2'-difluorocytidine 5'-triphosphate sodium salt
W-200827
2'-deoxy-2',2'-difluorocytidine 5'-triphosphate
gemcitabine-triphosphate
DTXSID80911928
1-[2-deoxy-2,2-difluoro-5-o-(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)pentofuranosyl]-4-imino-1,4-dihydropyrimidin-2-ol
gemcitabine-5'-triphosphate
gem tp
gemzar triphosphate
Q27273475
gemcitabinetriphosphate
ymoxeiokajsrqx-qppqhzfasa-n

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" In contrast to ara-C triphosphate, dFdCTP is eliminated with biphasic kinetics that exhibit a terminal half-life that approaches the cell cycle time."( Pharmacokinetics of the 5'-triphosphates of arabinosylcytosine and 2',2'-difluorodeoxycytidine in L1210 cells.
Grindey, GB; Plunkett, W, 1987
)
0.27
"Twenty patients were enrolled for both pharmacokinetic and clinical studies."( Pharmacokinetic evaluation of gemcitabine and 2',2'-difluorodeoxycytidine-5'-triphosphate after prolonged infusion in patients affected by different solid tumors.
Airoldi, M; Cattel, L; Delprino, L; Milla, P; Passera, R; Pedani, F, 2006
)
0.33

Bioavailability

ExcerptReferenceRelevance
" ALS-8176 (71), the 3',5'-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo."( Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
Beigelman, L; Blatt, LM; Chanda, SM; Deval, J; Dyatkina, N; Fung, A; Hong, J; Jin, Z; Liu, J; Prhavc, M; Serebryany, V; Smith, DB; Stevens, SK; Symons, JA; Tam, Y; Taylor, J; Wang, G; Zhang, Q, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" Tumor response was determined in animals receiving a similar dosing schedule of dFdCyd."( Tumor uptake and elimination of 2',2'-difluoro-2'-deoxycytidine (gemcitabine) after deoxycytidine kinase gene transfer: correlation with in vivo tumor response.
Blackstock, AW; Case, LD; Hess, SM; Lightfoot, H; Mitchell, BS; Mukherji, SK; Swarts, SG; Tepper, JE, 2001
)
0.31
"Pancreatic ductal adenocarcinoma tumour tissue from genetically engineered mouse models of pancreatic cancer (KP ( FL/FL ) C and KP ( R172H/+) C) was collected after dosing the mice with gemcitabine."( A novel method for quantification of gemcitabine and its metabolites 2',2'-difluorodeoxyuridine and gemcitabine triphosphate in tumour tissue by LC-MS/MS: comparison with (19)F NMR spectroscopy.
Bapiro, TE; Cook, N; Frese, KK; Goldgraben, MA; Griffiths, JR; Jacobetz, MA; Jodrell, DI; Madhu, B; Olive, KP; Richards, FM; Smith, DM; Tuveson, DA, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidoneA pyrimidine carrying one or more oxo substituents.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (7)

PathwayProteinsCompounds
Gemcitabine Action Pathway138
Gemcitabine Metabolism Pathway138
UTP and CTP de novo biosynthesis1321
superpathway of pyrimidine ribonucleosides salvage2237
superpathway of pyrimidine nucleobases salvage1126
superpathway of pyrimidine ribonucleotides de novo biosynthesis2345
superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis4662

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1200153Binding affinity to human mitochondrial RNA polymerase assessed as compound incorporation using [33P]RNA/DNA primer/templates used by agarose gel electrophoresis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
AID1200152Inhibition of human mitochondrial RNA polymerase assessed as 13-mer product using [33P]RNA/DNA primer/templates used by agarose gel electrophoresis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.88)18.7374
1990's2 (11.76)18.2507
2000's3 (17.65)29.6817
2010's10 (58.82)24.3611
2020's1 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.99

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.99 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (11.76%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (82.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]