Compounds > tak 013
Page last updated: 2024-11-10

tak 013

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

Cross-References

ID SourceID
PubMed CID3038517
CHEMBL ID22055
SCHEMBL ID209021
MeSH IDM0450749

Synonyms (37)

Synonym
5-{(benzyl(methyl)amino)methyl}-1-(2,6-difluorobenzyl)-6-(4-(3-methoxyureido)phenyl)-3-phenylthieno(2,3-d)pyrimidine-2,4(1h,3h)-dione
urea, n-(4-(1-((2,6-difluorophenyl)methyl)-1,2,3,4-tetrahydro-5-((methyl(phenylmethyl)amino)methyl)-2,4-dioxo-3-phenylthieno(2,3-d)pyrimidin-6-yl)phenyl)-n'-methoxy-
5-(n-benzyl-n-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-(4-(3-methoxyureido)phenyl)-3-phenylthieno(2,3-d)pyrimidine-2,4(1h,3h)-dione
308831-61-0
unii-56s17z6x9m
56s17z6x9m ,
sufugolix [inn:ban]
tak 013
1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(methyl-(phenylmethyl)amino)methyl]-2,4-dioxo-3-phenylthieno[4,5-e]pyrimidin-6-yl]phenyl]-3-methoxyurea
gtpl1185
sufugolix
tak-013
CHEMBL22055 ,
bdbm50122654
1-{4-[5-[(benzyl-methyl-amino)-methyl]-1-(2,6-difluoro-benzyl)-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidin-6-yl]-phenyl}-3-methoxy-urea
n-[4-(3-phenyl-5-(n-benzyl-n-methyl-aminomethyl)-1-(2,6-difluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl]-n''-methoxyurea
1-(4-(1-(2,6-difluorobenzyl)-5-((benzyl(methyl)amino)methyl)-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-3-methoxyurea
L001648
1-[4-[5-[[benzyl(methyl)amino]methyl]-1-[(2,6-difluorophenyl)methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea
sufugolix [inn]
5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-6-(4-(3-methoxyureido)phenyl)-3-phenylthieno(2,3-d)pyrimidine-2,4(1h,3h)-dione
SCHEMBL209021
5-(n-benzyl-n-methylaminomethyl)-l-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1h, 3h)-dione
5-(n-benzyl-n-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1h, 3h)-dione
n-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea
UCQSBGOFELXYIN-UHFFFAOYSA-N
DTXSID40184893
HY-100209
CS-6434
1-[4-(5-{[benzyl(methyl)amino]methyl}-1-[(2,6-difluorophenyl)methyl]-2,4-dioxo-3-phenyl-1h,2h,3h,4h-thieno[2,3-d]pyrimidin-6-yl)phenyl]-3-methoxyurea
mfcd09837896
AKOS030629545
sufugolix(tak-013)
1-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-3-methoxyurea
DB06494
AS-35342
Q21099001

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The results demonstrated that the thienopyrimidine-2,4-dione core is an excellent surrogate for the thienopyridin-4-one and that thienopyrimidine-2,4-diones and thienopyridin-4-ones constitute a new class of potent and orally bioavailable LHRH receptor antagonists."( Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
Cho, N; Endo, S; Fujino, M; Furuya, S; Harada, M; Nara, Y; Sasaki, S; Suzuki, N, 2003)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histone deacetylase Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
Gonadotropin-releasing hormone receptorHomo sapiens (human)IC50 (µMol)0.04110.00010.12895.2000AID102810; AID102813; AID102817; AID102818; AID257933; AID257934; AID257935; AID257936; AID257937; AID257938; AID257939; AID257940; AID257942; AID257943; AID257944; AID257945; AID257946; AID257947; AID257949; AID257950; AID257951; AID257953; AID257954; AID257956; AID257958; AID257959; AID257960; AID257961; AID257962; AID257963; AID257964; AID257965; AID257966; AID257967; AID257968; AID257969; AID257970; AID257971; AID257972; AID257973; AID257974; AID257975; AID257976; AID257977; AID257979; AID257980; AID257981; AID257982; AID257983; AID257984; AID257985; AID257986; AID257987; AID257988; AID257989; AID257990; AID257991; AID257992; AID257993; AID257994; AID257995; AID257996; AID257997; AID257998; AID257999; AID258000; AID258001; AID258002; AID258003; AID258004; AID258005; AID258006; AID258007; AID258008; AID258009; AID272532; AID272533; AID272534; AID272535; AID272536; AID272537; AID272538; AID272539; AID272540; AID272541; AID272542; AID272543; AID272557; AID272558; AID407893; AID606109; AID606111; AID606113; AID606115; AID607143
Gonadotropin-releasing hormone receptorHomo sapiens (human)Ki0.00020.00010.00290.0190AID74419
Gonadotropin-releasing hormone receptorRattus norvegicus (Norway rat)IC50 (µMol)0.50070.00030.15422.0000AID102824; AID606118
Type-2 angiotensin II receptorHomo sapiens (human)IC50 (µMol)0.00080.00010.02890.2000AID272557
Histone deacetylase 1Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.34513.5120AID258004
Histone deacetylase Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
Histone deacetylase 3Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
Gonadotropin-releasing hormone receptorMacaca mulatta (Rhesus monkey)IC50 (µMol)0.00060.00060.00230.0040AID407894
Histone deacetylase 7Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
Histone deacetylase 6 Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
Histone deacetylase 4Rattus norvegicus (Norway rat)IC50 (µMol)0.00630.00280.35173.5120AID258004
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
gonadotropin secretionGonadotropin-releasing hormone receptorHomo sapiens (human)
cellular response to gonadotropin-releasing hormoneGonadotropin-releasing hormone receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayGonadotropin-releasing hormone receptorHomo sapiens (human)
cellular response to hormone stimulusGonadotropin-releasing hormone receptorHomo sapiens (human)
blood vessel remodelingType-2 angiotensin II receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by circulatory renin-angiotensinType-2 angiotensin II receptorHomo sapiens (human)
angiotensin-mediated vasodilation involved in regulation of systemic arterial blood pressureType-2 angiotensin II receptorHomo sapiens (human)
brain renin-angiotensin systemType-2 angiotensin II receptorHomo sapiens (human)
cell surface receptor signaling pathwayType-2 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayType-2 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway coupled to cGMP nucleotide second messengerType-2 angiotensin II receptorHomo sapiens (human)
brain developmentType-2 angiotensin II receptorHomo sapiens (human)
regulation of blood pressureType-2 angiotensin II receptorHomo sapiens (human)
negative regulation of heart rateType-2 angiotensin II receptorHomo sapiens (human)
negative regulation of cell growthType-2 angiotensin II receptorHomo sapiens (human)
positive regulation of phosphoprotein phosphatase activityType-2 angiotensin II receptorHomo sapiens (human)
regulation of metanephros sizeType-2 angiotensin II receptorHomo sapiens (human)
exploration behaviorType-2 angiotensin II receptorHomo sapiens (human)
nitric oxide-cGMP-mediated signalingType-2 angiotensin II receptorHomo sapiens (human)
angiotensin-activated signaling pathwayType-2 angiotensin II receptorHomo sapiens (human)
vasodilationType-2 angiotensin II receptorHomo sapiens (human)
negative regulation of blood vessel endothelial cell migrationType-2 angiotensin II receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionType-2 angiotensin II receptorHomo sapiens (human)
negative regulation of neurotrophin TRK receptor signaling pathwayType-2 angiotensin II receptorHomo sapiens (human)
neuron apoptotic processType-2 angiotensin II receptorHomo sapiens (human)
positive regulation of metanephric glomerulus developmentType-2 angiotensin II receptorHomo sapiens (human)
positive regulation of branching involved in ureteric bud morphogenesisType-2 angiotensin II receptorHomo sapiens (human)
positive regulation of extrinsic apoptotic signaling pathwayType-2 angiotensin II receptorHomo sapiens (human)
inflammatory responseType-2 angiotensin II receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
peptide bindingGonadotropin-releasing hormone receptorHomo sapiens (human)
gonadotropin-releasing hormone receptor activityGonadotropin-releasing hormone receptorHomo sapiens (human)
angiotensin type II receptor activityType-2 angiotensin II receptorHomo sapiens (human)
protein bindingType-2 angiotensin II receptorHomo sapiens (human)
receptor antagonist activityType-2 angiotensin II receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneGonadotropin-releasing hormone receptorHomo sapiens (human)
membraneGonadotropin-releasing hormone receptorHomo sapiens (human)
plasma membraneGonadotropin-releasing hormone receptorHomo sapiens (human)
plasma membraneType-2 angiotensin II receptorHomo sapiens (human)
plasma membraneType-2 angiotensin II receptorHomo sapiens (human)
nucleoplasmHistone deacetylase 1Rattus norvegicus (Norway rat)
nucleoplasmHistone deacetylase 3Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (155)

Assay IDTitleYearJournalArticle
AID257949Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K115Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258004Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR F309L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257971Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S203K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257996Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D302N2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54882Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 2 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID272537Displacement of [His5, D-Tyr6]GnRH from GnRHR D302A mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257945Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L112A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258007Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N315A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257999Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N305D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272536Displacement of [His5, D-Tyr6]GnRH from GnRHR L300A mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID606109Displacement of [125I]leuprorelin from recombinant human GnRH receptor expressed in CHO cells after 60 mins by X-ray counter2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257953Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S118N2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407914AUC (0 to 6 hrs) in cynomolgus monkey at 10 mg/kg, po2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID272539Displacement of [His5, D-Tyr6]GnRH from GnRHR H306A mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257964Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257963Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S186K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257961Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H182E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258005Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR F309Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257950Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L117A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258008Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N315D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257988Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D293E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257955Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K121E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID26343pKa value was determined2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidine-2,4-dione derivatives as potent GnRH receptor antagonists.
AID257959Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S168I2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54883Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 24 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID272552Ratio of IC50 for GnRHR Y290L mutant to GnRHR F272Lmutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257987Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D293N2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257998Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N305A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407921AUC (0 to 8 hrs) in healthy male human at 200 mg2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID407918Cmax in healthy male human at 10 mg2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID272541Displacement of [His5, D-Tyr6]GnRH from GnRHR F309L mutant expressed in COS-7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272555Ratio of IC50 for GnRHR H306A mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272538Displacement of [His5, D-Tyr6]GnRH from GnRHR D302N mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257937Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N27A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID606112Lipophilicity, log D of the compound at pH 7.42011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID607157Antagonist activity at monkey GnRH receptor expressed in CHO cells assessed as inhibition of GnRH-induced arachidonic acid release using [5,6,8,9,11,12,14,15-3H]arachidonic acid preincubated for 15 mins measured after 45 mins by scintillation counting in 2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257986Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D293K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257940Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR T51A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257969Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K191E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257951Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S118A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257941Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N102D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID74419Binding affinity towards human gonadotropin-releasing hormone receptor2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidine-2,4-dione derivatives as potent GnRH receptor antagonists.
AID257936Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR M24T2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258003Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H306K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID607143Antagonist activity at human GnRH receptor expressed in CHO cells assessed as inhibition of GnRH-induced arachidonic acid release using [5,6,8,9,11,12,14,15-3H]arachidonic acid preincubated for 15 mins measured after 45 mins by scintillation counting in p2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257935Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR M24I2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257980Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y284L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257990Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E295K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272543Displacement of [His5, D-Tyr6]GnRH from GnRHR F313L mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID607156Plasma protein binding2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID54878Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 4 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257994Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L300V2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54743Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 0 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257962Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S186D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272532Displacement of [His5, D-Tyr6]GnRH from GnRHR M24I mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272554Ratio of IC50 for GnRHR D302N mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID606114Ratio IC50 for displacement of [125I]leuprorelin from human GnRH receptor expressed in CHO cells in presence of 40% fetal bovine serum to IC50 for displacement of [125I]leuprorelin from human GnRH receptor expressed in CHO cells2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID258002Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H306E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257966Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257942Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E111A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID28501Tested for oral absorption in Cynomolgus Monkey at the dose of 10 mg/kg, activity expressed as Cmax2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257938Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N27E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258000Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR N305K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54880Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 8 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257943Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E111K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID25983Tested for oral absorption in Cynomolgus Monkey at the dose of 10 mg/kg, activity expressed as area under curve (AUC)2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257934Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR M24A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257989Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E295A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54885Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 48 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257976Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR W280F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257973Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S203Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257939Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR A50T2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257995Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D302A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257958Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S168A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258001Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H306A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257946Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L112F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257948Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K115E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID19461Partition coefficient (logP)2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidine-2,4-dione derivatives as potent GnRH receptor antagonists.
AID257968Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR T190K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID606110Inhibition of human CYP3A4 assessed as conversion of testosterone to 6beta-hydroxytestosterone at 10 uM after 30 mins by HPLC analysis2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID272533Displacement of [His5, D-Tyr6]GnRH from GnRHR N27A mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID606115Antagonist activity at human GnRH receptor expressed in CHO cells assessed as inhibition of GnRH-induced arachidonic acid release using [5,6,8,9,11,12,14,15-3H]arachidonic acid preincubated for 15 mins measured after 45 mins by scintillation counting in p2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257954Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR K121A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54744Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 2 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257970Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S203E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257944Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E111Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257967Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189P2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272546Ratio of IC50 for GnRHR Q208E mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272534Displacement of [His5, D-Tyr6]GnRH from GnRHR Q208E mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257960Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR H182A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54879Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 48 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID407910Inhibition of circulating luteinizing hormone in cynomolgus monkey pituitary cells2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID272535Displacement of [His5, D-Tyr6]GnRH from GnRHR Y284L mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257977Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y283F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257933Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR F272L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257972Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S203P2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272542Displacement of [His5, D-Tyr6]GnRH from GnRHR F309Q mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272547Ratio of IC50 for GnRHR Y284L mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID606118Displacement of [125I]leuprorelin from rat GnRH receptor expressed in CHO cells after 60 mins by X-ray counter in presence of 40% fetal bovine serum2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID407908Binding affinity at cynomolgus monkey GnRH receptor expressed in CHO cells2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID606116Ratio of IC50 for human GnRH receptor in presence of 40% fetal bovine serum to IC50 for human GnRH receptor in absence of fetal bovine serum2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID606113Displacement of [125I]leuprorelin from recombinant human GnRH receptor expressed in CHO cells after 60 mins by X-ray counter in presence of 40% fetal bovine serum2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257979Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y284F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272550Ratio of IC50 for GnRHR F313L mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID54886Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 8 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID102817Antagonist concentration required to inhibit specific binding of [125I]leuprorelin to human luteinizing releasing hormone receptor in cloned chinese hamster ovary (CHO) cells.2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID407919AUC (0 to 8 hrs) in healthy male human at 10 mg2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID257975Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q208E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID102818Tested for inhibition of arachidonic acid(AA) release from CHO cells in Human2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257991Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR E295Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257974Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q208D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257957Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S124D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257956Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S124A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407912Suppression of circulating luteinizing hormone in cynomolgus monkey at 30 mg/kg, po relative to baseline2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID102813Tested for inhibition of arachidonic acid(AA) release from CHO cells in Monkey2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257981Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y290F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257983Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y290Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257984Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR W291F2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407894Binding affinity at monkey GnRH receptor2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID257947Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L112K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID606111Antagonist activity at human GnRH receptor expressed in CHO cells assessed as inhibition of GnRH-induced arachidonic acid release using [5,6,8,9,11,12,14,15-3H]arachidonic acid preincubated for 15 mins measured after 45 mins by scintillation counting2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID29714Tested for oral absorption in Cynomolgus Monkey at the dose of 10 mg/kg, activity expressed as Tmax (time required for Cmax)2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID272544Ratio of IC50 for GnRHR M24I mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID102810Tested for antagonist concentration required to inhibit specific binding of [125I]leuprorelin to LHRH receptor in monkey (chinese hamster ovary (CHO) cells)2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID257965Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Q189E2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407909Activity at cynomolgus monkey GnRH receptor expressed in CHO cells assessed as inhibition of arachidonic acid release2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID272553Ratio of IC50 for GnRHR D302A mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257993Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L300K2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID258009Displacement of [125I]-His5, D-Tyr6]GnRH from human wild type GnRHR2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407911Suppression of circulating luteinizing hormone in cynomolgus monkey at 10 mg/kg, po relative to baseline2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID54881Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 0 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID272556Ratio of IC50 for GnRHR H306E mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID102824Tested for antagonist concentration required to inhibit specific binding of [125I]leuprorelin to LHRH receptor in rat anterior pituitaries2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID258006Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR F313L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257985Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D293A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272548Ratio of IC50 for GnRHR F309L mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272540Displacement of [His5, D-Tyr6]GnRH from GnRHR H306E mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272545Ratio of IC50 for GnRHR N27A mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID407913Cmax in cynomolgus monkey at 10 mg/kg, po2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID257982Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y290L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID606117Displacement of [125I]leuprorelin from monkey GnRH receptor expressed in CHO cells after 60 mins by X-ray counter in presence of 40% fetal bovine serum2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadot
AID257978Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR Y283L2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID257997Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR D302Q2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID54884Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 30 mg/kg after 4 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID54745Tested for plasma LH concentration in Castarted male Cynomolgus monkeys for oral administration at the dose of 10 mg/kg after 24 h2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
AID407920Cmax in healthy male human at 200 mg2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID257952Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR S118D2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID272549Ratio of IC50 for GnRHR F309Q mutant to GnRHR F272L mutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272551Ratio of IC50 for GnRHR L300A mutant to GnRHR F272Lmutant2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID272558Displacement of [His5, D-Tyr6]GnRH from GnRHR Y290L mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
AID257992Displacement of [125I]-His5, D-Tyr6]GnRH from mutant GnRHR, GnRHR L300A2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Overlapping, nonidentical binding sites of different classes of nonpeptide antagonists for the human gonadotropin-releasing hormone receptor.
AID407893Binding affinity at human GnRH receptor2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Non-peptide gonadotropin-releasing hormone receptor antagonists.
AID272557Displacement of [125I]-His5, D-Tyr6]GnRH from GnRHR F272L mutant expressed in COS7 cells2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
Determination of the binding mode of thienopyrimidinedione antagonists to the human gonadotropin releasing hormone receptor using structure-activity relationships, site-directed mutagenesis, and homology modeling.
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.
AID1346002Human GnRH1 receptor (Gonadotrophin-releasing hormone receptors)2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: a highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (71.43)29.6817
2010's1 (14.29)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.26

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 Index12.26 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
t 98475
T 98475: structure in first source		3.5320isopropyl ester;
thienopyridine
ag045572
[no description available]		3.1410
tak 385
relugolix: structure in first source		2.0610
nbi 42902
[no description available]		3.5420
ConditionIndicatedRelationship StrengthStudiesTrials