Page last updated: 2024-11-07

talotrexin

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Description

N(alpha)-(4-amino-4-deoxypteroyl)-N(delta)-hemiphthaloyl-L-ornithine: RN refers to (S)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID130731
CHEMBL ID590985
SCHEMBL ID1060263
MeSH IDM0546162

Synonyms (26)

Synonym
unii-a8e516a20k
benzoic acid, 2-(((4-carboxy-4-((4-(((2-diamino-6-pteridinyl)methyl)amino)benzoyl)amino)butyl)amino)carbonyl)-, (s)-
talotrexin [inn]
a8e516a20k ,
nsc 623017
nsc-633713
113857-87-7
nsc-623017
pt523
n-(4-carboxy-4-{4-[(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoylamino}-butyl)-phthalamic acid
n(alpha)-(4-amino-4-deoxypteroyl)-n(delta)-hemiphthaloyl-l-ornithine
pt 523
talotrexin
CHEMBL590985
2-(((4s)-4-carboxy-4-((4-(((2,4-diaminopteridin-6-yl)methyl)amino)benzoyl)amino)butyl)carbamoyl)benzoic acid
talotrexin [who-dd]
benzoic acid,2-((((4s)-4-carboxy-4-((4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)amino)butyl)amino)carbonyl)-
SCHEMBL1060263
2-{[(4s)-4-carboxy-4-{[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)carbonyl]amino}butyl]carbamoyl}benzoic acid
2-[[(4s)-4-carboxy-4-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoy l]amino]butyl]carbamoyl]benzoic acid
DB06178
Q27273768
2-[[(4s)-4-carboxy-4-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]butyl]carbamoyl]benzoic acid
2-[[(4s)-4-carboxy-4-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoy l]amino]butyl]carbamoyl]benzo
CS-0002844
HY-10824

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" We defined each agent's clinical potency index (CPI) as the AUC achieved with standard pediatric dosing regimens divided by the in vitro IC50."( Clinical potency of methotrexate, aminopterin, talotrexin and pemetrexed in childhood leukemias.
Adamson, PC; Norris, RE, 2010
)
0.62
" Further clinical evaluation is warranted to investigate whether a low dosage of these antifolates can elicit immunosuppressive effects equivalent to MTX, and whether they are superior to MTX in patients who fail to respond to MTX."( Methotrexate analogues display enhanced inhibition of TNF-α production in whole blood from RA patients.
Assaraf, YG; Dijkmans, BA; Gerards, AH; Jansen, G; Lems, WF; Oerlemans, R; Scheper, RJ; van der Heijden, JW, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID459851Growth inhibition of Chinese hamster transporter null R2(VC) cells expressing human RFC after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID459846Growth inhibition of Chinese hamster RT16 cells expressing human FRalpha after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621123Antiproliferative activity against chinese hamster R2 cells assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459850Growth inhibition of Chinese hamster R2 cells expressing human RFC and human PCFT4 after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621136Inhibition of human RFC-mediated [3H]MTX uptake in chinese hamster PC43-10 cells at 10 uM after 2 mins relative to control2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID1513004Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as reduction in [3H]MTX uptake at pH 5.5 at 1 uM measured over 2 mins relative to control2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.
AID459847Growth inhibition of Chinese hamster RT16 cells expressing human FRalpha in presence of 200 nM folic acid after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621122Antiproliferative activity against chinese hamster PC43-10 expressing human RFC assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459848Growth inhibition of Chinese hamster D4 cells expressing human FRbeta after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID459844Growth inhibition of Chinese hamster PC43-10 cells expressing human RFC after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621130Antiproliferative activity against human KB cells expressing human RFC, FRalpha and PCFT assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621129Antiproliferative activity against chinese hamster R2(VC) cells expressing human PCFT assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621131Antiproliferative activity against human KB cells expressing human RFC, FRalpha and PCFT assessed as reduction of viable cells after 96 hrs in the presence of 200 nM folic acid2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621127Antiproliferative activity against chinese hamster D4 cells expressing human FRbeta assessed as reduction of viable cells after 96 hrs in the presence of 200 nM folic acid2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621126Antiproliferative activity against chinese hamster D4 cells expressing human FRbeta assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459853Growth inhibition of human KB cells expressing RFC, FRalpha and PCFT in presence of 200 nM folic acid after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID1513006Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as reduction in [3H]MTX uptake at pH 5.5 at 1 to 10 uM measured over 2 mins2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.
AID1513002Inhibition of human RFC2 expressed in human HeLa R1-11 cells assessed as reduction in [3H]MTX uptake at pH 7.2 at 10 uM measured over 2 mins relative to control2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.
AID1513033Inhibition of human RFC2 expressed in human HeLa R1-11 cells assessed as reduction in [3H]MTX uptake at pH 7.2 at 1 uM measured over 2 mins relative to control2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.
AID621124Antiproliferative activity against chinese hamster RT16 cells expressing human FRalpha assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621132Antiproliferative activity against human IGROV1 cells expressing human RFC, FRalpha and PCFT assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459845Growth inhibition of Chinese hamster R2 cells expressing human RFC after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID1513005Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as reduction in [3H]MTX uptake at pH 5.5 at 10 uM measured over 2 mins relative to control2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.
AID459854Growth inhibition of human IGROV1 cells expressing RFC, FRalpha and PCFT after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621133Antiproliferative activity against human IGROV1 cells expressing human RFC, FRalpha and PCFT assessed as reduction of viable cells after 96 hrs in the presence of 200 nM folic acid2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459852Growth inhibition of human KB cells expressing RFC, FRalpha and PCFT after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621125Antiproliferative activity against chinese hamster RT16 cells expressing human FRalpha assessed as reduction of viable cells after 96 hrs in the presence of 200 nM folic acid2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID621128Antiproliferative activity against chinese hamster R2 cells expressing human PCFT assessed as reduction of viable cells after 96 hrs2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
AID459849Growth inhibition of Chinese hamster D4 cells expressing human FRbeta in presence of 200 nM folic acid after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID459855Growth inhibition of human IGROV1 cells expressing RFC, FRalpha and PCFT in presence of 200 nM folic acid after 96 hrs2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduc
AID621170Inhibition of human PCFT-mediated [3H]MTX uptake ectopically expressed in chinese hamster R2 cells at 10 uM at pH 5.5 to 7.22011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-gl
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's11 (40.74)18.2507
2000's9 (33.33)29.6817
2010's6 (22.22)24.3611
2020's1 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.35

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 Index20.35 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]