Page last updated: 2024-10-15

ici 198583

Description

ICI 198583: RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135400203
CHEMBL ID434209
SCHEMBL ID9555830
MeSH IDM0166653

Synonyms (25)

Synonym
ici 198583
2-desamino-2-methyl-10-propagyl-5,8-dideazofolic acid
l-glutamic acid, n-(4-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-2-propynylamino)benzoyl)-
cb 3819
ici-198583
brn 4240992
CHEMBL434209 ,
2-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid
(s)-2-(4-(((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid
bdbm50006687
2-{4-[1-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl]-benzoylamino}-pentanedioic acid
(s)-2-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid
2-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid ;hydrate(2h2o)
(2s)-2-[[4-[(2-methyl-4-oxo-1h-quinazolin-6-yl)methyl-prop-2-ynylamino]benzoyl]amino]pentanedioic acid
unii-n8vp1y24au
112887-62-4
n8vp1y24au ,
zm-198583
cb-3819 ,
SCHEMBL9555830
DTXSID60150196
(2s)-2-[[4-[(2-methyl-4-oxo-3h-quinazolin-6-yl)methyl-prop-2-ynylamino]benzoyl]amino]pentanedioic acid
Q27284716
(S)-2-(4-(((2-METHYL-4-OXO-3,4-DIHYDROQUINAZOLIN-6-YL)METHYL)(PROP-2-YN-1-YL)AMINO)BENZAMIDO)PENTANEDIOIC ACID
AKOS040746913
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseHomo sapiens (human)IC50 (µMol)0.03990.00662.06379.5000AID212153; AID477806
Thymidylate synthaseMus musculus (house mouse)IC50 (µMol)0.04140.00041.322610.0000AID212478; AID212479; AID212485; AID212486; AID212492; AID212643; AID228250
Thymidylate synthaseMus musculus (house mouse)Ki0.02070.00341.73759.3000AID212653; AID212664
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
dTMP biosynthetic processThymidylate synthaseHomo sapiens (human)
dTTP biosynthetic processThymidylate synthaseHomo sapiens (human)
circadian rhythmThymidylate synthaseHomo sapiens (human)
response to xenobiotic stimulusThymidylate synthaseHomo sapiens (human)
response to toxic substanceThymidylate synthaseHomo sapiens (human)
negative regulation of translationThymidylate synthaseHomo sapiens (human)
uracil metabolic processThymidylate synthaseHomo sapiens (human)
methylationThymidylate synthaseHomo sapiens (human)
response to progesteroneThymidylate synthaseHomo sapiens (human)
response to vitamin AThymidylate synthaseHomo sapiens (human)
response to cytokineThymidylate synthaseHomo sapiens (human)
tetrahydrofolate interconversionThymidylate synthaseHomo sapiens (human)
response to ethanolThymidylate synthaseHomo sapiens (human)
response to organophosphorusThymidylate synthaseHomo sapiens (human)
developmental growthThymidylate synthaseHomo sapiens (human)
cartilage developmentThymidylate synthaseHomo sapiens (human)
response to glucocorticoidThymidylate synthaseHomo sapiens (human)
response to folic acidThymidylate synthaseHomo sapiens (human)
intestinal epithelial cell maturationThymidylate synthaseHomo sapiens (human)
DNA biosynthetic processThymidylate synthaseHomo sapiens (human)
liver regenerationThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
mRNA regulatory element binding translation repressor activityThymidylate synthaseHomo sapiens (human)
thymidylate synthase activityThymidylate synthaseHomo sapiens (human)
folic acid bindingThymidylate synthaseHomo sapiens (human)
protein homodimerization activityThymidylate synthaseHomo sapiens (human)
sequence-specific mRNA bindingThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusThymidylate synthaseHomo sapiens (human)
cytoplasmThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
mitochondrial inner membraneThymidylate synthaseHomo sapiens (human)
mitochondrial matrixThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID212485Concentration required to inhibit 50% activity of Thymidylate synthase was determined1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID212486Concentration required for in vitro inhibition of thymidylate synthase1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID97636Percent control for L1210 cell growth in the presence of thymidine (in vitro)1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series.
AID93927Compound was tested for relative resistance to L1210 (1565) cell line1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID212664Inhibition of thymidylate synthase, partially purified from L1210 mouse leukemia cells overexpressing TS1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Syntheses and thymidylate synthase inhibitory activity of the poly-gamma-glutamyl conjugates of N-[5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino ]-2-thenoyl]-L-glutamic acid (ICI D1694) and other quinazoline antifolates.
AID58146Inhibitory activity against Dihydrofolate reductase in rat liver1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID93928Compound was tested for relative resistance to L1210 (R7A) cell line1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID21135Solubility in 0.92 M aqueous NaH2PO4 buffer at pH 7.0 and 25 degree C1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID93925Concentration required to inhibit 50% growth of L1210 /1565 mutant mouse leukemia cell line was determined1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID99336Relative resistance ratio evaluated for murine tumor L1210:RD1694 cells with 10% horse serum as supplement1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID228250Inhibition of thymidylate synthase from L1210 cells1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Quinazoline antifolate thymidylate synthase inhibitors: difluoro-substituted benzene ring analogues.
AID99330Inhibition of cell growth in culture against murine tumor L1210:1565 cell lines1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID99331Relative resistance ratio evaluated for murine tumor L1210:1565 cells with 10% fetal calf serum as supplement1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID212153Inhibitory activity against thymidylate synthase (TS)1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some sulfonamidobenzoylglutamate and related derivatives.
AID99335Tested for inhibition of cell growth in culture against murine tumor L1210:RD1694 cell lines1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID101072Concentration required to inhibit 50 percent growth of L1210 mouse leukemia cells1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID98199Growth inhibition of murine tumor L1210 cell line1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID98516The compound was tested in vitro for the inhibition of L1210 cell growth in culture1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Quinazoline antifolate thymidylate synthase inhibitors: difluoro-substituted benzene ring analogues.
AID94431In vitro inhibition of L1210 cell growth in culture.1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Quinazoline antifolate thymidylate synthase inhibitors: heterocyclic benzoyl ring modifications.
AID212653Binding affinity against Thymidylate synthase was measured in vitro1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID212479In vitro inhibition of partially purified L1210 thymidylate synthase (TS).1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Quinazoline antifolate thymidylate synthase inhibitors: heterocyclic benzoyl ring modifications.
AID212492In vitro inhibition against L1210 thymidylate synthase (TS)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogues in the C2-methyl series.
AID97899The compound was tested for inhibition of isolated thymidylate synthase partially purified from L1210 mouse leukemia cells1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID212478Inhibition of partially purified thymidylate synthase (TS)1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series.
AID100451Tested for the concentration to inhibit 50% of L1210 cell growth in culture.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogues in the C2-methyl series.
AID98129Growth inhibition of L1210 cells in culture.1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series.
AID477806Inhibition of thymidylate synthase2010European journal of medicinal chemistry, Apr, Volume: 45, Issue:4
3D-QSAR studies on quinazoline antifolate thymidylate synthase inhibitors by CoMFA and CoMSIA models.
AID212643Inhibition of isolated thymidylate synthase partially purified from L1210 mouse leukemia cells1999Journal of medicinal chemistry, Sep-23, Volume: 42, Issue:19
Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors.
AID93926Concentration required to inhibit 50% growth of L1210 of R7A mutant mouse leukemia cell line was determined1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID97666The compound was tested in vitro for the inhibition of L1210 cell growth in the presence of thymidine1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Quinazoline antifolate thymidylate synthase inhibitors: difluoro-substituted benzene ring analogues.
AID96477Inhibition concentration against L1210 cells1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some sulfonamidobenzoylglutamate and related derivatives.
AID100494The inhibitory activity was determined on L1210 mouse leukemia cell in presence of thymidine1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
AID100496Concentration required to inhibit 50% growth of L1210 mouse leukemia cells was determined1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.94)18.7374
1990's30 (88.24)18.2507
2000's1 (2.94)29.6817
2010's2 (5.88)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other34 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]