Compounds > 5-fluorocytidine
Page last updated: 2024-11-05

5-fluorocytidine

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

Description

5-fluorocytidine, also known as 5FC, is a nucleoside analog that has been extensively studied as an antiviral and anticancer agent. It is a synthetic derivative of cytidine, where the hydrogen atom at the 5-position of the cytosine base is replaced with a fluorine atom. 5-fluorocytidine is known to inhibit the replication of viruses and the growth of cancer cells by interfering with DNA and RNA synthesis. It acts as a substrate for DNA polymerases, leading to the incorporation of the analog into the growing DNA chain. This incorporation results in chain termination and inhibits further DNA replication. 5-fluorocytidine has shown promise in the treatment of various viral infections, including herpes simplex virus, cytomegalovirus, and hepatitis B virus. It has also been investigated for its potential use in treating a range of cancers, including leukemia, lymphoma, and solid tumors. The fluorine atom in the molecule contributes to its enhanced stability and resistance to enzymatic degradation, thereby increasing its bioavailability and efficacy. 5-fluorocytidine's mechanism of action, its demonstrated antiviral and anticancer activity, and its unique chemical properties make it a valuable research target and a potential therapeutic agent in the treatment of various diseases.'

5-fluorocytidine: isolated from DNA of Escherichia coli grown in presence of 5-fluorouracil; structure; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID16861
CHEMBL ID490033
CHEBI ID38190
SCHEMBL ID207772
MeSH IDM0051111

Synonyms (36)

Synonym
AC-6193
5-fluorocytidine
CHEBI:38190 ,
cytidine, 5-fluoro-
2341-22-2
5-fluorocytidine, 97%
4-amino-1-[(2r,3r,4s,5r)-3, 4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one
fluc
bdbm31914
F0534
F01 ,
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-pyrimidin-2-one
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one
inchi=1/c9h12fn3o5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16h,2h2,(h2,11,12,17)/t4-,5-,6-,8-/m1/s1
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyr
strzqwqnzqmhqr-uakxsshosa-
CHEMBL490033
unii-vor4x0d7wr
vor4x0d7wr ,
c9h12fn3o5
4-amino-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-fluoropyrimidin-2(1h)-one
AKOS015896914
AKOS015853116
5-fluoro cytidine
SCHEMBL207772
3ELC
J-700093
PS-7362
4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one
mfcd00210953
DTXSID60177964
Q27117405
AMY254
PD120275
EN300-313811
Z3234819146
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
cytidines
[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]

Protein Targets (7)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
Chain C, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
Chain A, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
Chain A, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
Chain C, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
Chain A, 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12Kd2,020.00002,020.00002,020.00002,020.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
ubiquinone biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
isoprenoid biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
terpenoid biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
isopentenyl diphosphate biosynthetic process, methylerythritol 4-phosphate pathway2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
zinc ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
lyase activity2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
manganese ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
identical protein binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
metal ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1132729Antitumor activity against mouse S180 cells allografted in mouse assessed as tumor growth inhibition at 1 to 5 mg/kg, ip qd for 8 days1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Fluorinated Pyrimidine nucleosides. 1. Synthesis of a nitrogen analogue of the antitumor agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine hydrochloride.
AID154974Concentration required for antiviral activity in PBMC (human peripheral blood mononuclear cells) infected with HIV-1 strain LAV1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Structure-activity relationships of beta-D-(2S,5R)- and alpha-D-(2S,5S)-1,3-oxathiolanyl nucleosides as potential anti-HIV agents.
AID415022Binding affinity to Escherichia coli BL21 (DE3) IspF at 10 degC in pH 7 sodium phosphate buffer by SPR binding assay2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.
AID1799187SPR Biosensor Assay from Article 10.1021/jm801475n: \\A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.\\2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (60.00)18.7374
1990's2 (10.00)18.2507
2000's3 (15.00)29.6817
2010's2 (10.00)24.3611
2020's1 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.75

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.75 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index27.15 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cytosine
[no description available]		1.9610aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
orotic acid
Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.		1.9310pyrimidinemonocarboxylic acidEscherichia coli metabolite;
metabolite;
mouse metabolite
thymine
[no description available]		2.3520pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		7.8740nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
thymidine
[no description available]		1.9310pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
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.		1.9310nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
uridine
[no description available]		3.2160uridinesdrug metabolite;
fundamental metabolite;
human metabolite
cytidine monophosphate
Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.		2.0510cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-monophosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
cytidine
[no description available]		4.17170cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
2-fluoroadenosine
[no description available]		1.9610adenosines;
organofluorine compound
5-fluorouridine
[no description available]		3.2160organofluorine compound;
uridines		mutagen
azacitidine
Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.		1.9610N-glycosyl-1,3,5-triazine;
nucleoside analogue		antineoplastic agent
deoxycytidine
[no description available]		2.6530pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cyclic cmp
Cyclic CMP: A cyclic nucleotide formed from CYTIDINE TRIPHOSPHATE by the action of cytidylate cyclase. It is a potential cyclic nucleotide intracellular mediator of signal transductions.. 3',5'-cyclic CMP : A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.		2.05103',5'-cyclic pyrimidine nucleotidehuman 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.		1.9510diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		1.9810azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
cidofovir anhydrous
Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.		2.0510phosphonic acids;
pyrimidone		anti-HIV agent;
antineoplastic agent;
antiviral drug;
photosensitizing agent
lamivudine
[no description available]		1.9810monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.3920adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
5-methylcytosine
5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.		1.9610methylcytosine;
pyrimidines		human metabolite
1-beta-d-arabinofuranosylcytosine 5'-monophosphate
1-beta-D-arabinofuranosylcytosine 5'-monophosphate: RN given refers to dihydrogen phosphate		2.0510
5-fluoropyrimidine
[no description available]		1.9610
4-bromobenzenesulfonamide
4-bromobenzenesulfonamide: a metabolite of ebrotidine		2.0510
5-fluoroorotic acid
5-fluoroorotic acid: inhibits the dietary induction of serine dehydratase. 5-fluoroorotic acid : A pyrimidinemonocarboxylic that is orotic acid which is substituted by fluorine at position 5. It is used in yeast molecular genetics to detect expression of the URA3 gene, which encodes orotine-5'-monophosphate dicarboxylase. A yeast with and active URA3 gene converts 5-fluoroorotic acid to fluorodeoxyuridine, which is toxic to cells.		1.9310
nicotinohydroxamic acid
[no description available]		2.0510pyridinecarboxamide
pyrimidin-2-one beta-ribofuranoside
pyrimidin-2-one beta-ribofuranoside: RN given refers to (D)-isomer; structure		2.0710pyrimidine ribonucleosides
5-fluoropyrimidin-2-one beta-ribofuranoside
[no description available]		2.0710
5-fluoro-2'-deoxycytidine
5-fluoro-2'-deoxycytidine: structure		2.3520
ganciclovir
[no description available]		2.07102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
2-aminopurine dioxolane
(4-2-aminopurin-9-yl)-1,3-dioxolane-2-methanol: structure in first source		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
EHS Tumor
[description not available]		01.9510
Cancer of Colon
[description not available]		02.610
Colonic Neoplasms
Tumors or cancer of the COLON.		02.610
Cancer of Stomach
[description not available]		02.0710
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.0710
Benign Neoplasms
[description not available]		01.9310
Experimental Neoplasms
[description not available]		02.3520
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.		01.9310
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		01.9310
Group A Strep Infection
[description not available]		02.0310
Streptococcal Infections
Infections with bacteria of the genus STREPTOCOCCUS.		02.0310
Experimental Hepatoma
[description not available]		01.9610
Leukemia L5178
An experimental lymphocytic leukemia of mice.		01.9610