Page last updated: 2024-12-06

2-methylestradiol

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

Description

2-Methylestradiol (2-ME) is a synthetic estrogen analog that has shown potential in various research areas. It is typically synthesized via methylation of estradiol. 2-ME exhibits estrogenic activity and has been investigated for its potential applications in hormone replacement therapy, contraception, and the treatment of certain cancers. Research on 2-ME focuses on its binding affinity to estrogen receptors, its effects on different tissues and organs, and its potential therapeutic benefits and side effects. Its unique properties, including its increased stability compared to estradiol, make it a subject of ongoing research for diverse medical applications.'

2-methylestradiol: RN given refers to (17beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID66425
CHEMBL ID241993
SCHEMBL ID3868013
MeSH IDM0112807

Synonyms (13)

Synonym
NCI60_023222
2-methyl estradiol
nsc-666605
2-methylestradiol
CHEMBL241993 ,
(8r,9s,13s,14s,17s)-2,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
2-methyl estradiol 17-valerate
1818-12-8
estra-1,3,5(10)-triene-3,17-diol, 2-methyl-, (17beta)-
bdbm50369009
SCHEMBL3868013
DTXSID50939472
2-methylestra-1(10),2,4-triene-3,17-diol

Research Excerpts

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AromataseHomo sapiens (human)Ki0.10000.00000.60469.5010AID1270809
Tubulin beta-2B chainBos taurus (cattle)IC50 (µMol)17.00000.25001.88388.7000AID214038
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
negative regulation of chronic inflammatory responseAromataseHomo sapiens (human)
steroid biosynthetic processAromataseHomo sapiens (human)
estrogen biosynthetic processAromataseHomo sapiens (human)
androgen catabolic processAromataseHomo sapiens (human)
syncytium formationAromataseHomo sapiens (human)
negative regulation of macrophage chemotaxisAromataseHomo sapiens (human)
sterol metabolic processAromataseHomo sapiens (human)
female genitalia developmentAromataseHomo sapiens (human)
mammary gland developmentAromataseHomo sapiens (human)
uterus developmentAromataseHomo sapiens (human)
prostate gland growthAromataseHomo sapiens (human)
testosterone biosynthetic processAromataseHomo sapiens (human)
positive regulation of estradiol secretionAromataseHomo sapiens (human)
female gonad developmentAromataseHomo sapiens (human)
response to estradiolAromataseHomo sapiens (human)
microtubule-based processTubulin beta-2B chainBos taurus (cattle)
nervous system developmentTubulin beta-2B chainBos taurus (cattle)
positive regulation of axon guidanceTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
iron ion bindingAromataseHomo sapiens (human)
steroid hydroxylase activityAromataseHomo sapiens (human)
electron transfer activityAromataseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenAromataseHomo sapiens (human)
oxygen bindingAromataseHomo sapiens (human)
heme bindingAromataseHomo sapiens (human)
aromatase activityAromataseHomo sapiens (human)
GTPase activityTubulin beta-2B chainBos taurus (cattle)
metal ion bindingTubulin beta-2B chainBos taurus (cattle)
protein heterodimerization activityTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulumAromataseHomo sapiens (human)
endoplasmic reticulum membraneAromataseHomo sapiens (human)
membraneAromataseHomo sapiens (human)
endoplasmic reticulumAromataseHomo sapiens (human)
microtubule cytoskeletonTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID214038In vitro inhibition of tubulin polymerization.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID57875Cytotoxicity against prostate DU-145 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID102160Cytotoxicity against breast MDA-MB-435 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID200441Cytotoxicity against renal SN12C cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
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.
AID214193Percentage inhibition of colchicine binding to tubulin.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
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.
AID214754Cytotoxicity against melanoma UACC-62 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID80541Cytotoxicity against colon HCT116 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID1270809Competitive inhibition of human aromatase extracted from placental microsomes after 5 mins by Dixon plot analysis in presence of [1beta-3H]AD2015European journal of medicinal chemistry, Nov-13, Volume: 105Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer.
AID1337728Inhibition of recombinant human CYP1B1 expressed in bacterial microsomes co-expressing P450 reductase at 3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control2016Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21
Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.
AID90282Mean graph midpoint for all human cancer cell line cytotoxicity.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID201282Cytotoxicity against CNS SF-539 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID81509Cytotoxicity against lung HOP-62 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID145430Cytotoxicity against ovarian OVCAR-3 cancer cell lines.1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site.
AID297655Antiproliferative activity against human MCF7 cells 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.
AID70487Relative binding affinity for human estrogen receptor alpha1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
Three-dimensional models of estrogen receptor ligand binding domain complexes, based on related crystal structures and mutational and structure-activity relationship data.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (16.67)18.7374
1990's3 (25.00)18.2507
2000's3 (25.00)29.6817
2010's4 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.10

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 Index12.10 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.10)

All Compounds (24.57)

Study Types

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