Page last updated: 2024-11-12

rx-3117

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

Description

fluorocyclopentenylcytosine: has antineoplastic activity [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

roducitabine : A triol that is (1S,2R)-4-fluoro-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol which is substituted by a 4-amino-2-oxopyrimidin-1(2H)-yl group at position 5. It is a cytidine analog which exhibits anticancer activity in several cancers, including gemcitabine-resistant tumours. [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]

Cross-References

ID SourceID
PubMed CID11242315
CHEMBL ID2064455
CHEBI ID147412
SCHEMBL ID4409591
MeSH IDM000595349

Synonyms (42)

Synonym
fluorocyclopentenyl cytosine
rx 3117
fluorocyclopentenyl-cytosine
rx3117
4-amino-1-[(1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2(1h)-one
rx-3117
CHEBI:147412
fluorocyclopentenylcytosine
4-amino-1-[(1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-1,2-dihydropyrimidin-2-one
865838-26-2
roducitabine
tv-1360
1-[(1s,4r,5s)-2-fluoro-3-(hydroxymethyl)-4,5-dihydroxy-2-cyclopentenyl]cytosine
CHEMBL2064455
CS-3947
SCHEMBL4409591
AC-35336
HY-15228
0z4a82i0jo ,
unii-0z4a82i0jo
roducitabine [usan]
who 11374
4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-2(1h)-pyrimidinone
S900007480
AKOS027327327
4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)pyrimidin-2(1h)-one
4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)pyrimidin-2-one
4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl) cyclopent-2-en-1-yl) pyrimidin-2-one
2(1h)-pyrimidinone, 4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-
roducitabine [inn]
NCGC00485875-01
NCGC00485875-02
QLLGKCJUPWYJON-HLTSFMKQSA-N
4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-cyclopent-2-en-1-yl)-pyrimidin-2(1h)-one
4-amino-1-[(1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2-one
EX-A4776
DTXSID101113297
MS-23620
nsc785657
nsc-785657
4-amino-1-[(1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1h)-pyrimidinone
A900305

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" All patients experienced a treatment emergent adverse event (TEAE) with the most common diarrhea, nausea, and fatigue."( A multicenter phase 1/2 study investigating the safety, pharmacokinetics, pharmacodynamics and efficacy of a small molecule antimetabolite, RX-3117, plus nab-paclitaxel in pancreatic adenocarcinoma.
Babiker, H; Benaim, E; Borad, MJ; Bullock, AJ; Burhani, N; Elquza, E; Heaton, C; Hicks, LG; Mahadevan, D; Ocean, AJ; Peterson, C; Schlegel, PJ, 2022
)
0.92

Bioavailability

ExcerptReferenceRelevance
" Because of its tumor selective activation, novel mechanism of action, excellent oral bioavailability and candidate biomarkers for patient selection, RX-3117 has the potential to replace gemcitabine in the treatment of a spectrum of cancer types."( RX-3117 (fluorocyclopentenyl cytosine): a novel specific antimetabolite for selective cancer treatment.
Balboni, B; Benaim, E; El Hassouni, B; Giovannetti, E; Heaton, C; Honeywell, RJ; Kim, DJ; Lee, YB; Peters, GJ; Peterson, C; Poore, J; Sarkisjan, D, 2019
)
2.16
"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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
antimetaboliteA substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
DNA synthesis inhibitorAny substance that inhibits the synthesis of DNA.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
[role 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]

Drug Classes (3)

ClassDescription
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
primary allylic alcoholAn allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to two hydrogens.
triolA chemical compound containing three hydroxy groups.
[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]

Bioassays (47)

Assay IDTitleYearJournalArticle
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.
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.
AID1347160Primary screen NINDS Rhodamine 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.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings 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.
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.
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.
AID676560Antitumor activity against human A549 cells xenografted in ip dosed nu/nu mouse assessed as inhibition of tumor volume administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676526Antitumor activity against human MCF7 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676561Antitumor activity against human A549 cells xenografted in ip dosed nu/nu mouse assessed as inhibition of tumor weight administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676537Antitumor activity against human SK-MEL-28 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676525Antitumor activity against human OVCAR3 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676553Antitumor activity against human HCT116 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676540Antitumor activity against human MKN45 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676534Antitumor activity against human NCI-H226 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676551Antitumor activity against human NCI-H226 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676554Antitumor activity against human SK-MEL-28 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676549Antitumor activity against human A549 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676527Antitumor activity against human MDA-MB-231 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676552Antitumor activity against human HT-29 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676550Antitumor activity against human UMRC2 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676548Antitumor activity against human HepG2 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676563Inhibition of DNMT-1 protein human expression in MDA-MB-231 cells after 24 hrs by Western blot analysis2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676531Antitumor activity against human HepG2 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676558Antitumor activity against human K562 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676562Toxicity in nu/nu mouse xenografted with human A549 cells assessed as change in body weight 3 to 10 mg/kg, ip administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676544Antitumor activity against human MDA-MB-231 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676536Antitumor activity against human HCT116 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676547Antitumor activity against human LNCAP cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676532Antitumor activity against human A549 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676555Antitumor activity against human PANC1 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676529Antitumor activity against human PC3 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676538Antitumor activity against human PANC1 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676539Antitumor activity against human U251 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676559Antitumor activity against human A549 cells xenografted in ip dosed nu/nu mouse assessed as tumor growth inhibition administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676564Antitumor activity against human A549 cells xenografted in nu/nu mouse assessed as inhibition of tumor volume at 3 mg/kg, ip administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676557Antitumor activity against human MKN45 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676556Antitumor activity against human U251 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676541Antitumor activity against human K562 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676543Antitumor activity against human MCF7 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676542Antitumor activity against human OVCAR3 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676565Antitumor activity against human A549 cells xenografted in nu/nu mouse assessed as inhibition of tumor volume at 10 mg/kg, ip administered three times a week for 3 weeks2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676533Antitumor activity against human UMRC2 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676530Antitumor activity against human LNCAP cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676546Antitumor activity against human PC3 cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676528Antitumor activity against human HeLa cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676535Antitumor activity against human HT-29 cells by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
AID676545Antitumor activity against human HeLa cells at 1 uM by SRB method2012Journal of medicinal chemistry, May-10, Volume: 55, Issue:9
Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's10 (71.43)24.3611
2020's4 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.35

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 Index22.35 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (7.14%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]