Compounds > 2-methoxyestradiol-3,17-o,o-bis(sulfamate)
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2-methoxyestradiol-3,17-o,o-bis(sulfamate)

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Description

2-methoxyestradiol-3,17-O,O-bis(sulfamate): an antiangiogenic microtubule disruptor; antineoplastic agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9804302
CHEMBL ID218382
SCHEMBL ID446846
MeSH IDM0518297

Synonyms (27)

Synonym
(9beta,13alpha,14beta,17alpha)-2-methoxyestra-1,3,5(10)-triene-3,17-diyl disulfamate
2GD8
2-methoxyestradiol 3,17-o,o-bis-sulfamate
bdbm50200936
DB08416
CHEMBL218382 ,
2-meoe2bismate
stx140
stx-140
stx 140
3,17beta-bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene
2-methoxyestradiol-3,17-o,o-bis(sulfamate)
2-methoxyestradiol-3,17-o,o-bis-sulfamate
2-mbm
SCHEMBL446846
(9beta,17beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diyl disulfamate
(8r,9s,13s,14s,17s)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,17-diyl bis(sulfamate)
Q27097624
s57sqe6le5 ,
estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17beta)-
401600-86-0
unii-s57sqe6le5
2-methoxy-estra-1,3,5(10)-triene-3,17beta-diol, disulfamate
[(8r,9s,13s,14s,17s)-2-methoxy-13-methyl-3-sulfamoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] sulfamate
2-methoxyestradiol disulfamate
DTXSID501336467
(1s,3as,3br,9bs,11as)-8-methoxy-11a-methyl-7-(sulfamoyloxy)-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-1-yl sulfamate

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Therapies for hormone-independent prostate and breast cancer are limited, with the effectiveness of the taxanes compromised by toxicity, lack of oral bioavailability and drug resistance."( The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers.
Day, JM; Foster, PA; Ho, YT; Kasprzyk, PG; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Raobaikady, B; Reed, MJ, 2007)		0.34
"There is a continued need for orally bioavailable anticancer compounds that exhibit good efficacy against breast cancer."( A new micronized formulation of 2-methoxyestradiol-bis-sulfamate (STX140) is therapeutically potent against breast cancer.
Ali, T; Baronnet, MM; Bernetiere, S; Camara, J; Diolez, C; Foster, PA; Hacher, B; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Reed, MJ, )		0.13
"The new micronized formulation of STX140 is orally bioavailable and efficacious at inhibiting MDA-MB-231 breast tumor growth."( A new micronized formulation of 2-methoxyestradiol-bis-sulfamate (STX140) is therapeutically potent against breast cancer.
Ali, T; Baronnet, MM; Bernetiere, S; Camara, J; Diolez, C; Foster, PA; Hacher, B; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Reed, MJ, )		0.13
" These studies highlight the activity of two orally bioavailable anti-cancer agents one of which, STX140, may offer a significant clinical advantage over existing drugs as a common dose limiting factor, haemotoxicity, may be minimised."( A comparison of two orally bioavailable anti-cancer agents, IRC-110160 and STX140.
Ali, T; Foster, PA; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Reed, MJ; Stengel, C, )		0.13
" The compound was orally bioavailable (31% after a single 10 mg kg(-1) dose) and resistant to metabolism."( The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer.
Chander, SK; Foster, PA; Jhalli, R; Leese, MP; Newman, SP; Parsons, MF; Potter, BV; Purohit, A; Reed, MJ, 2008)		0.35
" In conclusion, STX140, a promising orally bioavailable anti-cancer agent in pre-clinical development, is highly efficacious in BCRP-expressing xenografts."( BCRP expression does not result in resistance to STX140 in vivo, despite the increased expression of BCRP in A2780 cells in vitro after long-term STX140 exposure.
Day, JM; Foster, PA; Ho, YT; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Reed, MJ; Tutill, HJ, 2009)		0.35

Dosage Studied

ExcerptRelevanceReference
" The potential of 4 as an orally dosed anti-tumor agent is confirmed using breast and prostate cancer xenografts."( 3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
Bubert, C; Ferrandis, E; Ho, YT; Kasprzyk, PG; Leese, MP; Mahon, MF; Newman, SP; Potter, BV; Purohit, A; Reed, MJ; Regis-Lydi, S, 2007)		0.34
" Furthermore, STX140 could be dosed daily over a 60-day period leading to tumour regression and complete responses, which were maintained after the cessation of dosing."( The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers.
Day, JM; Foster, PA; Ho, YT; Kasprzyk, PG; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Raobaikady, B; Reed, MJ, 2007)		0.34
" This is despite an increase in BCRP expression in A2780 cells in vitro after chronic dosing with STX140."( BCRP expression does not result in resistance to STX140 in vivo, despite the increased expression of BCRP in A2780 cells in vitro after long-term STX140 exposure.
Day, JM; Foster, PA; Ho, YT; Leese, MP; Newman, SP; Potter, BV; Purohit, A; Reed, MJ; Tutill, HJ, 2009)		0.35
" To determine TIX and pharmacological profile of STX140, a comprehensive dosing regime was performed in mice bearing MDA-MD-231 xenografts."( STX140, but not paclitaxel, inhibits mammary tumour initiation and progression in C3(1)/SV40 T/t-antigen transgenic mice.
Day, JM; Foster, PA; Kasprzyk, PG; Meyer-Losic, F; Newman, SP; Purohit, A; Reed, MJ, 2013)		0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)0.03900.03900.03900.0390AID977608
Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)0.37900.00021.10608.3000AID275898; AID317983
Carbonic anhydrase 2Homo sapiens (human)Ki0.27000.00000.72369.9200AID1624852
Steryl-sulfataseHomo sapiens (human)IC50 (µMol)0.03900.00010.40717.6000AID275881; AID317982
Carbonic anhydrase 9Homo sapiens (human)Ki0.07000.00010.78749.9000AID1624851
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 2Homo sapiens (human)Kd3.75000.00000.41575.5500AID1624854
Carbonic anhydrase 9Homo sapiens (human)Kd0.60500.00060.13420.6700AID1624853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
steroid catabolic processSteryl-sulfataseHomo sapiens (human)
female pregnancySteryl-sulfataseHomo sapiens (human)
epidermis developmentSteryl-sulfataseHomo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
steryl-sulfatase activitySteryl-sulfataseHomo sapiens (human)
sulfuric ester hydrolase activitySteryl-sulfataseHomo sapiens (human)
metal ion bindingSteryl-sulfataseHomo sapiens (human)
arylsulfatase activitySteryl-sulfataseHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
lysosomeSteryl-sulfataseHomo sapiens (human)
endosomeSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulumSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulum lumenSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulum membraneSteryl-sulfataseHomo sapiens (human)
Golgi apparatusSteryl-sulfataseHomo sapiens (human)
plasma membraneSteryl-sulfataseHomo sapiens (human)
membraneSteryl-sulfataseHomo sapiens (human)
intracellular membrane-bounded organelleSteryl-sulfataseHomo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (73)

Assay IDTitleYearJournalArticle
AID1624854Inhibition of carbonic anhydrase 2 (unknown origin) by isothermal calorimetry assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID1249508Antitumor activity against human MCF7 cells xenografted in nude mouse assessed as decrease in tumor volume at 20 mg/kg, po administered 5 days a week measured after 3 weeks2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID317973Antiproliferative activity against human HOP62 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID1249509Oral bioavailability in mouse at 10 mg/kg administered as single dose measured after 24 hrs2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID317975Antiproliferative activity against human SF539 cells at2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID317976Antiproliferative activity against human UACC62 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID473857Antiproliferative activity against human OVCAR-3 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473851Antiproliferative activity against human DU145 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473854Antiproliferative activity against human HCT116 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID317987Oral bioavailability in rat2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID317982Inhibition of steroid sulfatase-mediated conversion of [3H]E1S to E12008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID275889Growth inhibition of human SN12-C cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID317983Inhibition of human carbonic anhydrase 22008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID1249517Antitumor activity against human MDA-MB-231 cells xenografted in MF1 mouse administered thrice weekly2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID297654Antiproliferative activity against human MDA-MB-231 cells after 96 hrs by WST1 assay2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID1600019Oral bioavailability in mouse at 10 mg/kg2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID275895Antiangiogenic activity in HUVEC by chemotaxis assay2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1624852Inhibition of carbonic anhydrase 2 (unknown origin) by stopped-flow CO2 hydration assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID1624855Selectivity ratio of Ki for carbonic anhydrase 2 (unknown origin) to Ki for carbonic anhydrase 9 (unknown origin) expressed in Escherichia coli BL212019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID275881Inhibition of STS in placental microsomes by radiometric assay2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1249519Therapeutic index, ratio of LD50 for MF1 mouse to ED50 for human MDA-MB-231 cells xenografted in MF1 mouse administered thrice weekly2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID317977Antiproliferative activity against human OVCAR-3 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID473852Antiproliferative activity against human MDA-MB-231 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID1600027Antiproliferative activity against estrogen receptor-positive human MCF7 cells2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID473856Antiproliferative activity against human UACC62 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275903Inhibition of tumor growth in Lewis mouse lung carcinoma model at 30 mg/kg, iv2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1249510Antitumor activity against human MCF7 cells xenografted in mouse assessed as decrease in tumor volume at 5 mg/kg, po2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID1624853Inhibition of carbonic anhydrase 9 (unknown origin) expressed in Escherichia coli BL21 by isothermal calorimetry assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID317970Antiproliferative activity against human DU145 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID317972Antiproliferative activity against estrogen receptor negative human MDA-MB-231 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID275898Inhibition of human CA22006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID317978Antiproliferative activity against human SN12-C cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID473860Inhibition of bovine brain tubulin assembly assessed as decrease in turbidity after 20 mins2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275894Antiangiogenic activity assessed as inhibition of cord formation in HUVEC2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID317974Antiproliferative activity against human HCT116 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID317980Antiangiogenic activity against HUVEC cells assessed as inhibition of proliferation2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID1600028Antiproliferative activity against estrogen receptor-negative human MDA-MB-231 cells2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID275885Growth inhibition of human HOP62 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275897Inhibition of MDA-MB-435 growth xenografted in mouse at 20 mg/kg, po after 28 days2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID663555Inhibition of tubulin polymerization2012ACS medicinal chemistry letters, Jan-12, Volume: 3, Issue:1
Steroidomimetic Tetrahydroisoquinolines for the Design of New Microtubule Disruptors.
AID275892Growth inhibition of human SF539 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1600021Antitumor activity against human MCF7 cells xenografted in MF-1 nude mouse assessed as tumor growth inhibition at 5 mg/kg, po treated for 4 weeks by immunohistochemistry relative to control2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID1600020Antitumor activity against human MCF7 cells xenografted in MF-1 nude mouse assessed as tumor growth inhibition at 5 mg/kg, po treated for 4 weeks in presence of 2-deoxy-D-glucose by immunohistochemistry relative to control2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID473861Displacement of [3H]colchicine from bovine brain tubulin at 5 uM after 10 mins2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275888Growth inhibition of human OVCAR-3 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID317971Antiproliferative activity against estrogen receptor positive human MCF7 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID1249512Antitumor activity against mouse 4T1 cells xenografted in MF1 mouse assessed as decrease in tumor growth at 20 mg/kg/day for 8 weeks measured 3 weeks after dosing2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID663556Displacement of colchicine from tubulin at 5 uM2012ACS medicinal chemistry letters, Jan-12, Volume: 3, Issue:1
Steroidomimetic Tetrahydroisoquinolines for the Design of New Microtubule Disruptors.
AID275891Growth inhibition of human MDA-MB-435 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID663557Displacement of colchicine from tubulin at 50 uM2012ACS medicinal chemistry letters, Jan-12, Volume: 3, Issue:1
Steroidomimetic Tetrahydroisoquinolines for the Design of New Microtubule Disruptors.
AID473855Antiproliferative activity against human SF539 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473853Antiproliferative activity against human HOP62 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID1249518Toxicity in MF1 mouse assessed as mortality administered thrice weekly2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID1249513Antitumor activity against mouse 4T1 cells xenografted in MF1 mouse assessed as decrease in tumor growth at 20 mg/kg/day for 8 weeks measured 7 weeks after dosing2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID275886Growth inhibition of human HCT116 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1249511Antitumor activity against human MCF7 cells xenografted in mouse assessed as decrease in tumor volume at 5 mg/kg, po cotreated with microtubule inhibitor 2DG at 2 mg/kg, ip2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID1249514Antitumor activity against human MDA-MB-231 cells xenografted in MF1 mouse administered daily2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID473858Antiproliferative activity against human SN12C cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID317979Antiproliferative activity against human MDA-MB-435 cells2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents.
AID1624851Inhibition of carbonic anhydrase 9 (unknown origin) expressed in Escherichia coli BL21 by stopped-flow CO2 hydration assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID275887Growth inhibition of human UACC62 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275890Growth inhibition of human DU145 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275902Inhibition of tumor growth in Lewis mouse lung carcinoma model at 10 mg/kg, ip2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275893Antiangiogenic activity assessed as growth inhibition in HUVEC2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275896Inhibition of tumor growth in Lewis mouse lung carcinoma model at 2.5 mg/kg, ip2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275883Antiproliferative activity against human MCF7 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1249515Toxicity in MF1 mouse assessed as mortality administered daily2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID297653Antiproliferative activity against human DU145 cells after 96 hrs by WST1 assay2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID275899Oral bioavailability in rat2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1249516Therapeutic index, ratio of LD50 for MF1 mouse to ED50 for human MDA-MB-231 cells xenografted in MF1 mouse administered daily2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID275901Inhibition of tumor growth in Lewis mouse lung carcinoma model at 5 mg/kg, ip2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1811Experimentally measured binding affinity data derived from PDB2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (50.00)29.6817
2010's8 (40.00)24.3611
2020's2 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.36

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.36 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.55%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (95.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
anastrozole
[no description available]		2.1110nitrile;
triazoles		antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor
letrozole
[no description available]		2.1110nitrile;
triazoles		antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor
sulfamic acid
sulfamic acid: standard in alkalimetry; RN given refers to parent cpd; structure. sulfamic acid : The simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to hydroxy and amino groups and by double bonds to two oxygen atoms.		2.610sulfamic acids
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.4620taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
2-methoxyestradiol
2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.		3.699017beta-hydroxy steroid;
3-hydroxy steroid		angiogenesis modulating agent;
antimitotic;
antineoplastic agent;
human metabolite;
metabolite;
mouse metabolite
2-methylestradiol
2-methylestradiol: RN given refers to (17beta)-isomer		2.0310
deoxyglucose
Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.		2.0410
estrone-3-o-sulfamate
estrone-3-O-sulfamate: a steroid sulfatase inhibitor		3.8830
ym 511
YM 511: a non-steroidal aromatase inhibitor; structure given in first source		3.6520
irosustat
irosustat: Antineoplastic Agents, Hormonal; a tricyclic sulfamate ester; structure in first source		2.0410
fosbretabulin
[no description available]		2.4720stilbenoid
vorozole
vorozole: structure given in first source; vorozole/R 83842 is ((+)/dextro-isomer), RN 129731-10-8; R 83839 ((-)/levo-isomer)		2.1110benzotriazoles
estradiol-3-o-sulfamate
[no description available]		2.4620
2-meoemate
[no description available]		4.140
4-methylcoumarin 7-o-sulfamate
[no description available]		3.6520
2-ethylestradiol sulfamate
2-ethyloestradiol-bis-sulfamate: structure in first source		4.6880
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.0410benzenes;
hydroxycoumarin;
methyl ketone
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Lewis Lung
A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.		02.0310
Breast Cancer
[description not available]		03.6690
Angiogenesis, Pathologic
[description not available]		02.0310
Breast Neoplasms
Tumors or cancer of the human BREAST.		03.6690
Endometrioma
An enlarged area of ENDOMETRIOSIS that resembles a tumor. It is usually found in the OVARY. When it is filled with old blood, it is known as a chocolate cyst.		02.1110
Cancer of Prostate
[description not available]		02.9740
Endometriosis
A condition in which functional endometrial tissue is present outside the UTERUS. It is often confined to the PELVIS involving the OVARY, the ligaments, cul-de-sac, and the uterovesical peritoneum.		02.1110
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.9740
Allergic Encephalomyelitis
[description not available]		02.610
Malignant Melanoma
[description not available]		02.610
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.610
Disease Exacerbation
[description not available]		02.0810
Adenocarcinoma, Basal Cell
[description not available]		02.0810
Allodynia
[description not available]		02.0810
Cancer of Lung
[description not available]		02.0810
Peripheral Nerve Diseases
[description not available]		02.0810
Experimental Mammary Neoplasms
[description not available]		02.520
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.0810
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0810
Peripheral Nervous System Diseases
Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.		02.0810
Cancer of Ovary
[description not available]		02.4520
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.4520
Hormone-Dependent Neoplasms
[description not available]		02.4420
Carcinoma, Anaplastic
[description not available]		02.0410
Cancer of Endometrium
[description not available]		02.0410
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		02.0410
Endometrial Neoplasms
Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.		02.0410