Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H20O2 |
| Molecular Weight | 268.3502 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3C(=CCC4=CC(O)=CC=C34)[C@@H]1CCC2=O
InChI
InChIKey=WKRLQDKEXYKHJB-HFTRVMKXSA-N
InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1
| Molecular Formula | C18H20O2 |
| Molecular Weight | 268.3502 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Equilin is one of the active components of estrogens used in estrogen replacement therapy. This compound is used as a sulfate conjugate in drug Premarin. Equili is an inhibitor of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1), a key enzyme responsible for elevated levels of 17beta-estradiol (E2) in breast tumor tissues. Thus equilin reduce the E2 levels in breast tissues and hence the reduce risk of estrogen-dependent breast cancer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differing species responsiveness of estrogenic contaminants in fish is conferred by the ligand binding domain of the estrogen receptor. | 2014-05-06 |
|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013-09-05 |
|
| Tartrazine and sunset yellow are xenoestrogens in a new screening assay to identify modulators of human oestrogen receptor transcriptional activity. | 2012-08-16 |
|
| Synthesis and biological evaluation of (6- and 7-phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1. | 2011-01-13 |
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| Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
|
| Roles of hCG in Advancing Follicular Growth to Ovulation after Concurrent Injections of PGF(2α) and GnRH in Postpubertal Holstein Heifers Bearing a CL. | 2010-12-01 |
|
| Pharmacokinetics of a modified-release estrogen tablet. | 2010-11-04 |
|
| A component of Premarin(®) enhances multiple cognitive functions and influences nicotinic receptor expression. | 2010-11 |
|
| Equine estrogens impair nitric oxide production and endothelial nitric oxide synthase transcription in human endothelial cells compared with the natural 17{beta}-estradiol. | 2010-09 |
|
| DNA-Destabilizing Agents as an Alternative Approach for Targeting DNA: Mechanisms of Action and Cellular Consequences. | 2010-07-25 |
|
| Equine estrogen-induced mammary tumors in rats. | 2010-04-01 |
|
| Influence of alkalinity and salinity on the sonochemical degradation of estrogen hormones in aqueous solution. | 2010-02-15 |
|
| Molecular clustering of endometrial carcinoma based on estrogen-induced gene expression. | 2009-11 |
|
| Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol. | 2009-10-30 |
|
| Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: II. Fast screening of free steroids and related low-molecular-mass compounds fraction in the environmental samples derived from surface waters, treated and untreated sewage waters as well as activated sludge material. | 2009-10-30 |
|
| NMR and computational studies of stereoisomeric equine estrogen-derived DNA cytidine adducts in oligonucleotide duplexes: opposite orientations of diastereomeric forms. | 2009-08-04 |
|
| Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination. | 2009-01 |
|
| Structure activity relationships and differential interactions and functional activity of various equine estrogens mediated via estrogen receptors (ERs) ERalpha and ERbeta. | 2008-10 |
|
| Determination of absolute configurations of 4-hydroxyequilenin-cytosine and -adenine adducts by optical rotatory dispersion, electronic circular dichroism, density functional theory calculations, and mass spectrometry. | 2008-09 |
|
| Proliferation of the superficial epithelium of ovaries in senile female rats following oral administration of conjugated equine estrogens. | 2008-06 |
|
| Analysis of steroidal estrogens as pyridine-3-sulfonyl derivatives by liquid chromatography electrospray tandem mass spectrometry. | 2008-04-01 |
|
| Steady-state pharmacokinetics of conjugated equine estrogens in healthy, postmenopausal women. | 2008-02 |
|
| Effects of estrogens and selective estrogen receptor modulators on vascular reactivity in the perfused mesenteric vascular bed. | 2007-11 |
|
| Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants. | 2007-09 |
|
| Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases. | 2007-08-31 |
|
| Ultrasound-induced destruction of low levels of estrogen hormones in aqueous solutions. | 2007-08-15 |
|
| Ultrasound assisted destruction of estrogen hormones in aqueous solution: effect of power density, power intensity and reactor configuration. | 2007-07-31 |
|
| Effects of the components of hormone therapy on matrix metalloproteinases in breast-cancer cells: an in vitro study. | 2007-04 |
|
| 4-hydroxyequilenin-adenine lesions in DNA duplexes: stereochemistry, damage site, and structure. | 2007-01-09 |
|
| Translesion synthesis past equine estrogen-derived 2'-deoxyadenosine DNA adducts by human DNA polymerases eta and kappa. | 2006-05-16 |
|
| Active site analysis of 17beta-hydroxysteroid dehydrogenase type 1 enzyme complexes with SPROUT. | 2006-03-27 |
|
| Select estrogens within the complex formulation of conjugated equine estrogens (Premarin) are protective against neurodegenerative insults: implications for a composition of estrogen therapy to promote neuronal function and prevent Alzheimer's disease. | 2006-03-13 |
|
| The estrogen metabolite 17beta-dihydroequilenin counteracts interleukin-1alpha induced expression of inflammatory mediators in human endothelial cells in vitro via NF-kappaB pathway. | 2006-01 |
|
| Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics. | 2005-11-08 |
|
| Separation and detection of the isomeric equine conjugated estrogens, equilin sulfate and delta8,9-dehydroestrone sulfate, by liquid chromatography--electrospray-mass spectrometry using carbon-coated zirconia and porous graphitic carbon stationary phases. | 2005-08-12 |
|
| Mixtures of estrogenic contaminants in bile of fish exposed to wastewater treatment works effluents. | 2005-04-15 |
|
| Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors. | 2005-02 |
|
| [Menopause in 2004: "hormone replacement therapy" is not what it used to be anymore]. | 2004-11 |
|
| Translesion synthesis past equine estrogen-derived 2'-deoxycytidine DNA adducts by human DNA polymerases eta and kappa. | 2004-09-07 |
|
| Targeting oestrogen to kill the cancer but not the patient. | 2004-03-08 |
|
| Equine estrogens differentially inhibit DNA fragmentation induced by glutamate in neuronal cells by modulation of regulatory proteins involved in programmed cell death. | 2003-12-23 |
|
| B-ring unsaturated estrogens: biological evaluation of 17alpha-Dihydroequilein and novel B-Nor-6-thiaequilenins as tissue selective estrogens. | 2003-12-15 |
|
| Comparison of the proliferative effects of estradiol and conjugated equine estrogens on human breast cancer cells and impact of continuous combined progestogen addition. | 2003-09 |
|
| Equine estrogens differentially prevent neuronal cell death induced by glutamate. | 2003-07 |
|
| Potential role of the interaction between equine estrogens, low-density lipoprotein (LDL) and high-density lipoprotein (HDL) in the prevention of coronary heart and neurodegenerative diseases in postmenopausal women. | 2003-06-20 |
|
| Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's. | 2003-06 |
|
| Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin. | 2003-06 |
|
| Conformations of stereoisomeric base adducts to 4-hydroxyequilenin. | 2003-06 |
|
| Interaction of endogenous compounds in human and rat urine with P-glycoprotein. | 2002 |
|
| Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+. | 1999-02-02 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:36:15 GMT 2025
by
admin
on
Mon Mar 31 18:36:15 GMT 2025
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| Record UNII |
08O86EX0J4
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| Record Status |
Validated (UNII)
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| Record Version |
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C2293
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10971
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08O86EX0J4
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474-86-2
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DB02187
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C29020
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223368
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42309
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EQUILIN
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m4970
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PRIMARY | Merck Index |
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ACTIVE MOIETY |
