Compounds > 2',2'-difluorodeoxycytidine 5'-triphosphate
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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
triphosphoric acid
triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure		2.610acyclic phosphorus acid anhydride;
phosphorus oxoacid
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		4.231nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
cytidine diphosphate
Cytidine Diphosphate: Cytidine 5'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.		2.1310cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-diphosphate		Escherichia coli metabolite;
mouse metabolite
uridine triphosphate
Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.		3.9721pyrimidine ribonucleoside 5'-triphosphate;
uridine 5'-phosphate		Escherichia coli metabolite;
mouse metabolite
cytidine triphosphate
Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.		8.87152cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite
cytarabine
[no description available]		1.9710beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
deoxycytidine
[no description available]		13.3992pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.4320diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
arabinofuranosylcytosine triphosphate
Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis.		2.4120
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		8.5102organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
carboplatin
[no description available]		2.9610
4'-azidocytidine
4'-azidocytidine: antiviral; structure in first source		2.1110N-glycosyl compound
ribose
ribopyranose : The pyranose form of ribose.		2.0510D-ribose;
ribopyranose
2',2'-difluoro-2'-deoxyuridine
2',2'-difluoro-2'-deoxyuridine: structure given in first source; metabolic deamination product of gemcitabine. 2',2'-difluoro-2'-deoxyuridine : A pyrimidine 2'-deoxyribonucleoside that is uridine in which the hydroxy group at position 2' has been replaced by two fluoro substituents. It is a metabolite of the drug gemcitabine.		4.231
als-8176
4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine: an antiviral with RSV polymerase inhibitory activity; structure in first source		2.1110
cobamamide
cobamamide : A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12.		2.4620
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Respiratory Syncytial Virus
[description not available]		02.1110
Respiratory Syncytial Virus Infections
Pneumovirus infections caused by the RESPIRATORY SYNCYTIAL VIRUSES. Humans and cattle are most affected but infections in goats and sheep have been reported.		02.1110
Benign Neoplasms
[description not available]		04.7821
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		04.7821
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0610
Carcinoma, Non-Small Cell Lung
[description not available]		03.3820
Cancer of Lung
[description not available]		03.3820
Cancer of Pancreas
[description not available]		02.5220
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		03.3820
Lung Neoplasms
Tumors or cancer of the LUNG.		03.3820
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.5220
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.9610
Breast Cancer
[description not available]		03.5611
Breast Neoplasms
Tumors or cancer of the human BREAST.		03.5611
Cancer of Liver
[description not available]		02.1710
Carcinoma, Ductal, Pancreatic
[description not available]		02.1710
Liver Neoplasms
Tumors or cancer of the LIVER.		02.1710
Carcinoma, Pancreatic Ductal
Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.		02.1710
Experimental Neoplasms
[description not available]		0210
Acute Lymphoid Leukemia
[description not available]		02.8910
Precursor Cell Lymphoblastic Leukemia-Lymphoma
A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.		02.8910
Leucocythaemia
[description not available]		02.8910
Cells, Neoplasm Circulating
[description not available]		02.8910
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.8910
Leukemia L 1210
[description not available]		01.9710