Page last updated: 2024-11-12

5-chloro-6-(1-(2-iminopyrrolidinyl) methyl)uracil hydrochloride

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

Description

tipiracil hydrochloride : A hydrochloride obtained by combining tipiracil with one equivalent of hydrochloric acid. Used in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer. [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 CID9903778
CHEMBL ID65375
CHEBI ID90877
SCHEMBL ID1682924
MeSH IDM0304941

Synonyms (56)

Synonym
chembl65375 ,
tas-1-462
tipiracil hydrochloride
S3731
unii-4h59klq0a4
4h59klq0a4 ,
tipiracil hydrochloride [usan]
183204-72-0
tipiracil hydrochloride (jan/usan)
D10467
tipiracil hydrochloride [mi]
tipiracil hydrochloride [who-dd]
tas-102 component tipiracil hydrochloride
s-95005 component tipiracil hydrochloride
5-chloro-6-(2-imino-pyrrolidin-1-yl)methyl-2,4(1h,3h)-pyrimidinedione hydrochloride
2,4(1h,3h)-pyrimidinedione, 5-chloro-6-((2-imino-1-pyrrolidinyl)methyl)-, hydrochloride (1:1)
lonsurf component tipiracil hydrochloride
tipiracil hydrochloride [jan]
tipiracil hydrochloride component of lonsurf
tipiracil hydrochloride [orange book]
HY-A0063
tipiracil (hydrochloride)
CS-1637
5-chloro-6-(1-(2-iminopyrrolidinyl)methyl)uracil hydrochloride
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4-(1h,3h)-pyrimidinedione hydrochloride
KGHYQYACJRXCAT-UHFFFAOYSA-N
5-chloro-6-(1-(2-iminopyrrolidinyl)-methyl)uracil hydrochloride
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4(1h,3h)-pyrimidinedione hydrochloride
1-[(5-chloro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl]pyrrolidin-2-iminium chloride
tipiracil.hcl
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4(1h,3h)-dione hydrochloride
CHEBI:90877
tipiracil monohydrochloride
SCHEMBL1682924
tipiracil hcl
AC-30634
J-690251
EX-A882
ma-1 hydrochloride
AKOS027427002
5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1h,3h)-dione hydrochloride
tipiracil hydrochloride, >=98% (hplc)
FT-0700247
BCP06245
Q27162848
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-1h-pyrimidine-2,4-dione;hydrochloride
EX-A1393
mfcd01571384
5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1h,3h)-dione hcl
AMY25415
CCG-267234
AS-56082
A847265
5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1h,3h)-dione hydrochloride;tipiracil hcl
DTXSID001027748
5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1h,3h)-dionehydrochloride
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
EC 2.4.2.4 (thymidine phosphorylase) inhibitorAn EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of thymidine phosphorylase (EC 2.4.2.4).
[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 (2)

ClassDescription
hydrochlorideA salt formally resulting from the reaction of hydrochloric acid with an organic base.
iminium saltSalts in which the cation has the structure R2C=N(+)R2. Thus N-hydronated imines and their N-substituted derivatives.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine phosphorylaseEscherichia coli K-12IC50 (µMol)0.02270.00271.79146.5000AID1055574; AID241246; AID241389; AID415489; AID589642
Thymidine phosphorylaseHomo sapiens (human)IC50 (µMol)0.03140.02001.58386.8000AID1055579; AID1335972; AID1402655; AID1402656; AID1497670; AID213303; AID241061; AID363294; AID757420
Thymidine phosphorylaseHomo sapiens (human)Ki0.01900.00130.27042.6000AID238361; AID363294; AID456853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
DNA damage responseThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleobase metabolic processThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleoside metabolic processThymidine phosphorylaseEscherichia coli K-12
thymidine metabolic processThymidine phosphorylaseEscherichia coli K-12
mitochondrial genome maintenanceThymidine phosphorylaseHomo sapiens (human)
angiogenesisThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleobase metabolic processThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleoside metabolic processThymidine phosphorylaseHomo sapiens (human)
chemotaxisThymidine phosphorylaseHomo sapiens (human)
signal transductionThymidine phosphorylaseHomo sapiens (human)
cell differentiationThymidine phosphorylaseHomo sapiens (human)
regulation of myelinationThymidine phosphorylaseHomo sapiens (human)
dTMP catabolic processThymidine phosphorylaseHomo sapiens (human)
regulation of transmission of nerve impulseThymidine phosphorylaseHomo sapiens (human)
regulation of gastric motilityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
thymidine phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
glycosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
pentosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein bindingThymidine phosphorylaseHomo sapiens (human)
growth factor activityThymidine phosphorylaseHomo sapiens (human)
thymidine phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein homodimerization activityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolThymidine phosphorylaseEscherichia coli K-12
membraneThymidine phosphorylaseEscherichia coli K-12
cytosolThymidine phosphorylaseEscherichia coli K-12
cytosolThymidine phosphorylaseHomo sapiens (human)
cytosolThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID1055579Competitive inhibition of human thymidine phosphorylase in presence of thymidine2013European journal of medicinal chemistry, , Volume: 70Fragment-based approach to the design of 5-chlorouracil-linked-pyrazolo[1,5-a][1,3,5]triazines as thymidine phosphorylase inhibitors.
AID1402662Antiangiogenic activity against human HUVEC assessed as inhibition of capillary/tube-like network formation at 0.05 uM after 20 to 40 hrs by microscopic analysis2018European journal of medicinal chemistry, Jan-20, Volume: 144Synthesis and biological evaluation of novel 1-(aryl-aldehyde-oxime)uracil derivatives as a new class of thymidine phosphorylase inhibitors.
AID236065Bioavailability in mouse (dose 20 mg/kg p.o.)2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID237024Steady state volume of distribution was measured in mice after intraperitoneal administration of 10 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236740Maximum concentration was measured in mice after intravenous administration of 2 mg/kg; N/A = not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236983Maximum time to attain Cmax in mice after intravenous administration of 2 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1335972Inhibition of human placenta thymidine phosphorylase using [6-3H]dThd as substrate after 5 mins by scintillation counting method2016European journal of medicinal chemistry, Nov-29, Volume: 124Recent discovery of non-nucleobase thymidine phosphorylase inhibitors targeting cancer.
AID236154Concentration at time 0 was measured in mice after oral administration of 20 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236438Area under concentration-time curve for the compound was measured in mice after oral administration of 20 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236115Bioavailability in mouse (dose 2 mg/kg i.v.)2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236968Maximum time to attain Cmax in mice after oral administration of 20 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID456853Inhibition of human recombinant thymidine phosphorylase2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase.
AID363294Inhibition of human recombinant thymidine phosphorylase by [3H]thymidine incorporation assay2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID236153Concentration at time 0 was measured in mice after intravenous administration of 2 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1402655Inhibition of human placental thymidine phosphorylase using [6-3H]dThd as substrate after 5 mins by scintillation counting analysis2018European journal of medicinal chemistry, Jan-20, Volume: 144Synthesis and biological evaluation of novel 1-(aryl-aldehyde-oxime)uracil derivatives as a new class of thymidine phosphorylase inhibitors.
AID237022Steady state volume of distribution was measured in mice after intravenous administration of 2 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236977Maximum time to attain Cmax in mice after intraperitoneal administration of 10 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID589642Inhibition of Escherichia coli Thymidine phosphorylase by spectrophotometry2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Structure-activity relationship of 2,4,5-trioxoimidazolidines as inhibitors of thymidine phosphorylase.
AID415489Inhibition of Escherichia coli thymidine phosphorylase2009Bioorganic & medicinal chemistry, Apr-15, Volume: 17, Issue:8
Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors.
AID241246Inhibition of Thymidine phosphorylase from Escherichia coli2004Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21
Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase.
AID238361Inhibitory activity against thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1055574Inhibition of Escherichia coli recombinant thymidine phosphorylase using thymidine as substrate after 4 to 20 mins by UV spectrophotometry2013European journal of medicinal chemistry, , Volume: 70Fragment-based approach to the design of 5-chlorouracil-linked-pyrazolo[1,5-a][1,3,5]triazines as thymidine phosphorylase inhibitors.
AID236098Bioavailability in mouse (dose 10 mg/kg i.p.)2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236947Half-life was measured in mice after intravenous administration of 2 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID757420Inhibition of human thymidine phosphorylase2013European journal of medicinal chemistry, Jul, Volume: 65Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase.
AID236256Clearance at time 0 was measured in mice after intravenous administration of 2 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID241389Inhibitory concentration against thymidine phosphorylase of Escherichia coli2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236950Half-life was measured in mice after intraperitoneal administration of 10 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236655Maximum plasma concentration in mice after oral administration of 20 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID241061Inhibitory concentration against human thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236259Clearance at time 0 was measured in mice after oral administration of 20 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236263Clearance at time 0 was measured in mice after intraperitoneal administration of 10 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID237023Steady state volume of distribution was measured in mice after oral administration of 20 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1402656Inhibition of thymidine phosphorylase (unknown origin) using thymidine as substrate after 1 hr by spectrophotometric analysis2018European journal of medicinal chemistry, Jan-20, Volume: 144Synthesis and biological evaluation of novel 1-(aryl-aldehyde-oxime)uracil derivatives as a new class of thymidine phosphorylase inhibitors.
AID236460Area under concentration-time curve for the compound was measured in mice after intravenous administration of 2 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID213303Compound was evaluated for its inhibitory activity against recombinant purified Escherichia coli Thymidine Phosphorylase2003Journal of medicinal chemistry, Jan-16, Volume: 46, Issue:2
Potential tumor-selective nitroimidazolylmethyluracil prodrug derivatives: inhibitors of the angiogenic enzyme thymidine phosphorylase.
AID236943Half-life was measured in mice after oral administration of 20 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236155Concentration at time 0 was measured in mice after intraperitoneal administration of 10 mg/kg; not available2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236469Area under concentration-time curve for the compound was measured in mice after intraperitoneal administration of 10 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID236707Maximum concentration was measured in mice after intraperitoneal administration of 10 mg/kg2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1497670Inhibition of human placenta thymidine phosphorylase using [6-3H]dThd as substrate after 5 mins by scintillation counting method2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Rational design of bis-indolylmethane-oxadiazole hybrids as inhibitors of thymidine phosphorylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's7 (58.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.94

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 Index11.94 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]